First Five: First Date (Pt.1)

Now we’ve made it past First Contact and you’ve been chatting and talking with someone you’re interested in, let’s discuss (for some) possibly the most nerve-racking part of dating – the First Date.

First, I’ll discuss a little about getting, setting up and leading up to that First Date. Then we’ll talk about what and what not to do on that First Date, as well as a few pointers for following up after the date.

—-[ Let’s PAUSE here for a second]—-

OK, I wanted to put this up front, instead of burying it at the end because I think it’s something you all need to understand (since this is a women-heavy readership).

Men KNOW pretty much after the first date. No, they don’t exactly know you are “The One”,  but they do know whether or not you have the potential to be “The One” and whether they want to pursue it further or not. If he keeps pursuing you and asking you out, that means he still sees you filled with potential. He’s not asking you out to just see how it goes or to “feel things out”, as most women like to say. Now, here’s the asterisk to that: this only applies to good men who are looking for actual relationships, not hookups.

—-[Back to your regularly scheduled programming]—-

Before you get the First Date, you have to set up the First Date. Now, the first thing you have to do is gauge your partner, because some people like to chit chat online, email or text for a long time before deciding to go out with someone, while others want to just cut through the nonsense and get right to the physical meeting to see if there is any chemistry, as well as to avoid wasting valuable time with someone they end up not feeling compatible with. If you aren’t good at “reading the room”, then just ask. It’s that easy.

Now to some important tips I’ve put together about setting up the first date. This applies to the men, not women.

  • Be the man! Ask her out before she has to ask you. Even if she is head-over-heels interested in you and anxious to go out with you, you’re the man – You Ask Her!
  • Give her plenty of time to prepare for the date. If I want to go out with a girl that weekend, I generally ask early in the week. You don’t know if they already have plans for the weekend, but you want to get your foot in the door before other offers come along. Tuesday is generally my target day for asking a girl out.
  • If she says No, at first. Don’t just give up. Give her more time instead. Maybe she just wants to “feel things out” a little more. Don’t get discouraged. If she is still talking to you, she is still interested in you – remember that. And whatever you do, don’t be an insecure jerk about it and pout or get pissy with her. You’re shutting the door on yourself with that kind of behavior.
  • When she says Yes, then Man Up again and set up the date. Don’t her ask her what she wants to do, or where she would like go. Take the initiative and plan something. If she has a problem with it, like you want sushi and she’s allergic, or something like that, then adjust with a little input. But the initial plan should be All You.
  • Now, going back to my first bullet point, if you’re really good and on your game, you can make it much easier by combining the asking and planning in one simple step. It also makes it harder for her to say No. You don’t really even ask her out, you kind of backdoor it. Just say something like “Why don’t we do sushi and go see (whatever good date RomCom is out) Friday night?” She can’t just say No, she has to come up with a bonafide reason why not and explain it to you. You will cut rejections down significantly approaching it that way. Simply saying “Do you want to go out Friday?” leaves the door wide open for her to give you a simple No answer.
  • Lastly. NEVER plan a Night In for the first date. Make the effort to take her out somewhere nice, in a public setting where she will feel more comfortable. Suggesting a night in watching movies and drinking, etc., just says “I want to just hook-up with you, that’s it.” Don’t be that guy. Date Nights In will come soon enough, and you’ll have plenty of time for that. But start things off on the right foot.

With the First Date set, let’s talk about what should happen on the date. But we will talk about that next time. Otherwise, this post would be so long no one would read it all.  So, logically this is a good breaking point.

Stay tuned for Part 2 to follow shortly. Are you following on Twitter to get updates? Or click the “Follow” button on the right to get updates from the latest posts.

And as always, thanks for reading!

Introducing Bella (my stylist, first offline date)

Many sayings could apply here. Sometimes you have to go off the grid. OR Sometimes you have to get back to the basics. No matter what it is, it’s ironic.

I say it’s ironic, because after all the money I’ve spent online dating, it seems meeting someone the old-fashioned way (flirting and talking with someone in public) works just as well, if not better than online.

So let’s start at the beginning. Bella is my hair stylist, my exclusive stylist. She’s also the only one my son let’s cut his hair. I can’t tell you how long it has been, definitely more than a year now, maybe close to two years.

We’ve always had good rapport and find it real easy to talk to each other. My son always walks out of the salon saying “You guys are hysterical together.” He even suggested several times that her and I date.

But there’s a problem, OK, maybe two problems. First, I have a strict policy about trying to pick up waitresses, bartenders (i.e. Zoey), Hooters girls, strippers, or any woman who makes her money interacting with men for tips – especially at her workplace. Now, don’t get me wrong, I’ve dated all of the above at one time or another, but I’ve never picked them up at their work. I’ve met them outside of work and found out they were a bartender or waitress. Well, except for strippers, I met them at the club. So sue me.

The second issue is I’m 42 and she’s 25 (birthday in June). I’m 16.5 years older than she is and she’s barely 7 years older than my older son.

But she’s funny, smart, in shape, and absolutely beautiful. And we connect so well. She also has two little boys (4 and 14 months) and is divorced.

However, back in the Summer I decided to step up my conversations with her. I made them more flirty, playful, with several comments that – even though were fairly innocent – had plenty of built-in innuendo for someone who’s looking for sexually charged comments. And that’s precisely when I also noticed her demeanor changed toward me.

Without going into too much detail (yes, this is the abridged version), we made a bet on the World Series in November. When we made the bet, she asked what she would get if she won, I said “Anything you want.” And I confirmed that several times with her during the conversation. All of this took place while she was cutting my hair. Then, when I went to pay, I asked her what I would get if I won the bet, she replied with the same thing, “Anything you want.”

It was on! I knew right there what my “prize” was going to be. I was going to have her go on a date with me.

I won the bet. We had seen each other a few times at the salon after the bet and had talked about settling it, but I was too reluctant to tell her what I wanted, for fear she would reject it. I tried getting her to tell me what she would have picked if she had won, and she wouldn’t tell me.

Then came my birthday, last month. I was in getting my haircut on my birthday, as was my son. But we were on a time crunch. Remember, that was also the night of my first date with Ariel. And Bella always has a long wait-list of guys waiting just to have her cut their hair. So I just took the first girl who was available. When I sat down in Andrea’s chair, Bella was cleaning her station and started making comments like I was cheating on her and such. I retorted with comments like clearly I wasn’t a priority in her life, etc. She saw my son there and grabbed his ticket and began cutting his hair.

We talked back and forth across the salon the entire time. Andrea and the two other stylists were getting a kick out the banter back and forth. We went into the back to wash my hair, and Bella and my son soon followed. We continued the conversations )and flirting).

When I was done getting my hair washed, Andrea noticed my tattoos on my arm which I had recently had done. She was admiring them, so I was pulling up my sleeve to show all the work that goes up my arm and onto my chest. After that, we went back to finish up in the salon. Shortly after, my son took his seat back in Bella’s chair.

He tells me that she got his shirt wet. I asked how. He said she was distracted looking at my tattoos when I was showing them to Andrea and wasn’t paying attention and got water all over the front of his shirt. So across the salon, I said (loud enough for all to hear), “Oh, so you were checking me out, huh?” She turned 50 shades of red and had to turn away to hide her face she was blushing and so embarrassed.

Right then I knew I had her. So after we were all done, I was at the counter paying Andrea for both haircuts. When we were finished, Bella already had a new client in her chair. I walked back into the salon and from across the room said, “I’m not done with you yet,” and we walked out.

About a week later, I got a weird Facebook friend request. I didn’t recognize the name or the small picture on my phone, and we had no friends in common. So I didn’t open it right away. Later that night I finally got around to opening it. Then it hit me! It was her! Bella from the salon.

She stalked me – it was so sweet. She went into her work system and pulled out my full name and looked me up on Facebook. (Now I know she debated for days whether to send me something or not.) We chatted on Messenger for a few days before exchanging numbers. We’ve talked everyday since, and I mean we’ve talked a lot.

And yes, this was all overlapping my time with Ariel. But I wasn’t sure Bella was really serious about me, or us for that matter. But then last week, with Ariel pulling away and something clearly being wrong, and Bella obviously showing showing interest in me, I started to play along with the conversation as it escalated.

It was just talking and I was fully reserving my time for Ariel, if that is what worked out. Well, coincidentally or ironically or however you want to put it, Bella said she wanted to see me this weekend yesterday – just ask Ariel was preparing to have the break-up talk with me. So we made plans. She wanted to see me for breakfast Friday, Friday night as well as Saturday night. I committed to Friday plans, holding back on Saturday until I heard from Ariel.  Obviously, I committed to Saturday once things with Ariel fell through.

We had breakfast late this morning in between her time at the gym and before she had to go to work. It was really fun, friendly and flirty. She was nervous the whole place was listening to our conversations about the bet, guys flirting with her at work, and other such nonsense. We also discussed plans for the evening. She gets off work late and has to work all day Saturday, so she wants to just chill and watch a movie at her place.

I walked her to her car and we lingered chatting for a few minutes. A nearby was getting ready to pull out of the lot. As soon as it did, I pulled her close me and we embraced at first, holding each other tighter and tighter. I released a little, allowing her to pull back just enough to make room to kiss her. It wasn’t your typical first date kiss. She even grabbed my face as we kissed for a couple of minutes, even though it seemed so much longer.

So things definitely look promising, and I will – of course – update you on the rest of our weekend together.

And as always, thanks for reading!

The “First Five” of Dating

I’ll be the first to admit I’m not dating expert. I’m still single three years post-divorce and in my 40s. But one thing I do have is experience. And that experience seems to help others a lot more than it helps me.

Over the next few weeks, I’m going to be talking about what I call the “First Five of Dating.” These are the First Five milestones of any dating relationship. We’ll cover each one individually and in depth, but we’ll go over each one here real quick.

The First Five of Dating are the:

  1. First Contact
  2. First Date
  3. First Kiss
  4. First Sex
  5. First Time Saying “I Love You

First Contact is the first time you reach out to your prospective date, whether in person or online. It sets the tone for everything else to come.

First Date is, obviously, when to set the first date, how to prepare and what to do and what not to do.

First Kiss, again, is obvious, but it’s still something we need to discuss.

First Sex is a bit more tricky than the previous three. We’ll talk about how long is appropriate to wait, how to read the signs, how to test the waters, and more. No tricks!

First Time Saying “I Love You is a much more delicate and patient step. It could take weeks, maybe months, but we’ll discuss when it’s appropriate and also how to read the signs so you don’t scare your date off.

While putting this together, I had debated – and even had it recommended – that I also include the “First Fight” in this list. But I want to keep this positive. Developing a strong relationship should be based on positives. Yes, there are going to be disagreements, there always are. But that doesn’t belong here. Maybe I’ll address the “First Fight” on it’s own another time.

So please stop back and follow the discussion. You can sign up for email updates by clicking the “Follow” box in the right column, or follow me on Twitter. Please send any questions you have about each discussion ahead of time and I will try to answer or address each one, if I can. And please make sure you join each discussion.

As always, thanks for reading, and I will see you all again soon.

Introducing Ariel

To say that 2016 has started off poorly, is a grand understatement. January has been pretty much the worst month I can remember in a very long time. Not only the way it started with Zoey, but also many personal issues which you’re not interested in hearing here.

But things are hopefully starting to pick up.

I had been following through with my vow to not get back on Match until February, in order to avoid the Valentine’s Day new-relationship awkwardness. But last weekend I was updating my profile for when I decided to get back into the swing of the online dating game. You’d think I was new to this, because I didn’t realize that editing my profile made it “live” after months of having it hidden. I didn’t realize it until the flood of winks and notifications came in. Most of them completely bogus – thank you Match.

But there were a few “live ones” on there. So I decided to just give it a shot since my profile was public and ladies were checking it out.

That’s where Ariel came in. Her profile was very much what I was looking for. She’s tall enough (my perfect girl is about 5’8″-5’9″ because I’m 6’2″), active enough (she likes to run 5/10Ks and works out almost everyday), likes my kind of music, and even commented on looking good in a ballcap and formal dress. I once had a line almost exactly like that about wanting someone who looks good both in a ballcap and LBD.

So I messaged her. After about two days, we both decided to take the conversation off Match. I originally set up a date for us to get together this weekend (Saturday). But a friend of mine offered to watch my son on my birthday (Thursday) if I wanted to go out and do something for my birthday. So I asked Ariel if she was free and wanted to go out Thursday. She accepted.

A little about Ariel. She has one child, an 18 year old son who is a freshman in college, just like my oldest. She is only six months younger than me and works in the financial department of a very cool non-profit. And has the biggest, most intoxicating smile.

Ariel was mentioned numerous times that she felt very special that I chose to spend my birthday with her, and make that our first date. We met at the restaurant, and she arrived with a gift. I was very surprised she brought me a gift. It wasn’t much, just a gourmet cupcake and a very sweet card. The conversation was great and there was a lot of laughing. Always a good sign.

I walked her to her car, and as you regular readers know, I’m not the best at judging the “first kiss” and often back out instead of face the possible rejection. But tonight was not one of those nights. It seemed very natural and easy. It was just a quick kiss, but there was nothing uncomfortable about it.

As we parted, I reminded her that we were still on for Saturday and she wasn’t getting out of it. She completely agreed.

Friday, we texted a bit in the morning. She told me she was informed that she was just officially offered a job at the non-profit she used to for prior to her current job. She was really looking forward to this opportunity. The weather had been in the 60’s recently and we were discussing how nice it was. So I suggested – half joking – that she skip out on the afternoon at work and we go celebrate the new of her new job. I fully expected her to decline my offer because of work. But she didn’t. She jumped at the invitation.

So, I picked her up at her office and we went to a nearby bar for drinks and appetizers. Again, the conversation was great. No awkward silences or moments, and there was even more laughter. She’s totally tuned into my sense of humor and I don’t have to explain my jokes to her. It is so nice.

As I returned from a bathroom break, I noticed a lounge area with couches and loveseats. When I got back to the table, I mentioned the couches and she said she totally forgot about them and that next time we’ll have to hit the couch area instead. I drove her back to her office, and in the car we kissed goodbye again. This time was a little more intense than the first time.

But before she got out of the car, she commented that Saturday night she promised to be more affectionate. I totally understood because we were saying goodbye in the parking lot of her work. I had not said anything or acted in any adverse way because the thought of something “more” in that situation had never crossed my mind. So I really took that comment as a very good sign.

Saturday night went just as well, if not better. Though I was more nervous Saturday than I was for either of the first two dates, combined. We went to a japanese steakhouse and had wine in the waiting area talking about karaoke because she admitted she was a closet karaoke singer. Then during dinner, we were having a great time “people watching.” There was a younger couple sitting across the hibachi from us who looked like they were having a miserable time. By the end of dinner, we had decided to ask them to join for the rest of the night to get their real story and maybe cheer them up. However, they vanished as soon as the check was paid and we never had the chance.

We went to a nearby big country bar after dinner for drinks. We were talking, laughing, dancing, singing, kissing, holding hands and each other, and lots more “people watching”.

It was probably the best date I’ve been on in a very long time. She parked right next to me in the parking garage because she pulled into the garage right behind me. Normally I would have picked her up, but she lives about 30 minutes North of downtown and I live about 30 minutes South of downtown, so we just met downtown. We walked back hand in hand and when we got to her car, the goodnight kiss was much more intense and lingered for quite a while. Unfortunately, I had to return home to relieve the babysitter even though every ounce of my body wanted to stay there with her all night.

Today, we talked a little this morning and she spends Sundays going to church and spending time with her family (sisters and parents). She was making Mardi Gras King Cakes with her sister. I asked how that was going and jokingly said she needed to make one for me. Again, she enthusiastically agreed to have one for me “the next time she sees me”.

So everything seems to be starting off well. But I am much more cautious this time around, for better or worse. I am trying not to get my hopes up too high, given the way recent dating experiences have gone. Though many of my friends are telling me to not worry about it so much. One big change I’ve made is dialing back the texting. I’ve heard more than one source cite too much texting as being a key problem to developing relationships. So I am trying to make sure I space things out and not send every text that comes to mind. Hopefully it all equates to a better result.

Again, thank you for reading. And if you have any further questions or comments, please let me know.

Until next time …

Next Post: Ariel: I Made Her BFF Cry

This is Why I Hate Online Dating, or At Least One of the Big Reasons

There are lots of things to hate about online dating, and only a few things to like. As I always say, it’s a necessary evil – at least for me. And this right here is one of them.

When you’re talking to more than one person and you’ve only got a limited amount of time to make dates, who do you pick and how do you prioritize?

Here’s my situation: As you all know, I’ve gone out with Wanda and have another date set for Thursday. But I’m still talking to a couple of girls that I’ve been communicating with since before I went out with Wanda. Since I don’t want to assign names to them yet, I’ll just call them Potential 1 (P1) and Potential 2 (P2). I would drop P1 and P2 in a heartbeat if I knew things with Wanda were solid. But we’ve only been out once, and recent history has me leery about abandoning other possibilities because you never know what’s going to happen.

Like I said, I have a date scheduled for Thursday with Wanda, but both P1 and P2 have been pressuring me about wanting to do something this next weekend. I am available this weekend. I already tried to book it with something with Wanda, but she has two charity fundraisers this coming weekend. That’s why we’re going out Thursday. I have been skirting the issue trying to avoid committing either way.

Look, I don’t want to date anyone else but Wanda. Period. The signs are all good …

But again, you never know …

I hate the thought of having to go back on Match and start all over again. So let’s break down options I have, and I’m interested to see what you think.

Wanda

You’ve read about the first date. But since then, we did have a hiccup with having to cancel the original date. However, unlike recent incidents (Violet), she immediately rescheduled and has been completely normal with me ever since. She sends me random pictures just about every day of what she’s doing or something interesting. She sent me a picture of her riding her lawn mower wearing a baseball hat, in her bikini top, all while wearing big blue hearing protection. The hearing protection was not flattering, but it was still cute. She was also out shopping for dresses for her fundraisers (that I mentioned) and was sending me pictures of dresses she was trying on. We talk on the phone pretty much every day. She has this cute – kind of high-pitched – voice that is so sweet to hear. She’s even engaging on my Facebook page, like posts and pictures and even commenting.

From the beginning, I have known she is very much like me, in that she doesn’t like talking with a lot of people at the same time and definitely doesn’t like dating more than one at a time. She likes to focus on one at a time, too. And I don’t get the feeling she’s got other options going on along with me.

Now, my interpretation is that if she wasn’t really interested in me, she wouldn’t share the pictures and other things we talk about. If she was just lukewarm on me and us, I’d hear from her just enough to keep things going until the next date (Thursday). But we are also flirty and have lots of good conversations.

Again, I’d be more than happy to shut everything down to focus on her. And I don’t want to make a date with P1 or P2 for the weekend if things go really well with Wanda Thursday night. But I also don’t want to miss an opportunity with either one of them if something goes wrong with Wanda by or on Thursday night. Because then it would be really too late to make plans with either P1 or P2. Thus my dilemma.

Prospect 1

P1 lives just as far away as Wanda, but not in the same town. So, again I’d be compromising my stance on the long distance thing. She’s very much a country girl with blonde hair, green eyes and two kids (a teen girl and boy about the same age as my son). She’s very much into nature, exercising, and sports. She is also the one who seems to be the most interested in me between her and P2. She’s a dental assistant who happens to work in the same town as Wanda, and is always active with something with her kids, her friends or work.

She seems very sweet and genuine. She’s about 5’7″ and very much in shape. Not like Wanda, but her body looks very good in every picture I’ve seen. Now to be bluntly honest, she’s cute but still a little plain compared to what I’m used to. But at this point, that doesn’t seem to be any sort of detractor. If it wasn’t for Wanda, I’d have already set up some time to meet with her. She’s very interesting, and she is the most attentive out of all three options.

She, too, sends me frequent pictures of her and what she’s doing. She’s very respectful of what I have going on and is not demanding of my time. I don’t have any negatives to speak of with her.

Prospect 2

P2 is the most aggressive of the three options. She’s very flirty and playful and likes staying up late on the phone flirting and getting into deep discussions. She is very much into sports as well, and is also active and exercises frequently. She even does fun 5Ks like I do. However, physically, she isn’t the normal type of woman I look for. She’s much more curvy, but still in shape. She’s very cute and looks exactly like Blair from “The Facts of Life”. Again, it is no way a detractor when it comes to how I feel about her or the potential I think she has.

She’s an accountant with 3 kids and is working late on accounts or always shuttling kids from one activity to another. But she clearly likes me and definitely makes time to talk to me. She, too, has been very vocal and eager about finding a time to meet. From talking with her, it sounds like chemistry between the two of us would be rather easy. I would have her listed above P1 on the list as far as my top priority after Wanda, if it wasn’t for a little hiccup we had the other night.

We were talking late, per usual, and she was asking questions about what I was looking for in my woman. I was honest about what I expect and what i’m looking for. She took a few things I said about things I wouldn’t compromise on as being “still angry” about things that happened in past relationships. I said I was in no way angry, just explaining why I have the rules and expectations I have. I don’t want to get burned or taken advantage of again. But she still kept going with that. I finally said she was clearly reading something into what I was saying that wasn’t there. Since then, she has clearly backed off from me. We still talk everyday, but she isn’t nearly as flirty and isn’t sending me pictures daily, like she used to. She says it is because she is very tired, which may very well be the case, but I’m waiting for things to return to normal and still haven’t seen it. So we shall see.

Look, I like the potential I see in both P1 and P2. And I would hate to dismiss both of them, only to find myself back on Match full time next weekend because things didn’t work out with Wanda and I didn’t have any plans.

I don’t like stringing people along. I don’t like having other options still available if Wanda is actually focused on me. I know how I feel when I’m on the other side of that coin. Remember my thoughts on the Talia situation.  But I also know things are still early with Wanda and anything could happen in the next few days or by next weekend.

Do I set up something for Saturday with P1 or P2 and cancel if things go well with Wanda Thursday? Do I hold off until Friday to analyze things with Wanda and try to set up something last minute with either P1 or P2? Or do I set up something with P1 or P2 Saturday and keep it regardless of what happens with Wanda Thursday? Or what other suggestions do you have?

So what are your thoughts? Please leave your comments and even questions below, and lets dialogue about what you think I should do. I’m interested to hear your perspectives, especially from the lady readers out there.

Wanda: Former Fitness Model bends the dating rules in her favor

I wasn’t supposed to go out with Wanda until tomorrow night. She was coming into town for work and to catch a baseball and since she lives more than an hour away, so she’d stay with her good friend that she stays with on her frequent visits here. We really wanted to get together to meet before I went out of town for Labor Day weekend.

But today, she had the day off from work because she’s been traveling for nearly a week straight. She was telling me all of the stuff that she had to do today, including mowing and bailing her acreage. I was working from home today and playfully said I was available if she needed a playful distraction. I totally meant for her to call or text me. She immediately took it an ran with it as an excuse for us to see each other today. She prefaced it with saying she’d only be casual, with her hair in a pony tail and probably little to no makeup.

So we decided to meet this afternoon in the college town located midway between us, at a popular soda shop that sells just about every imaginable type and brand of soda (including international brands). Before I get into the date itself, how about a little background …

Wanda contacted me on Match with a fairly long, detailed message “selling” herself on why I should check her out and give her a chance, very similar to what Uma did. The main concern was her distance away from me. She lives more than an hour away, and my preferences are set to keep things rather local, because on top of my rigorous schedule with my son, having a partner living that far away only complicates the matter further. But she explained that she travels into town frequently for her job, is considering moving here, and has the flexibility with having two older kids (18 and 16) along with an 8 year old (like my son) who spends lots of time with his dad.

She also mentioned the fact that my Age parameters are set to 45 years old – and she’s 46. I’m sure that was much more of a joke, whereas the distance issue was an actual concern.

She travels frequently as an event planner/coordinator for a major bank setting up their corporate events across the country. And, yes – as I mentioned, she used to be a competitive fitness model. Something I did not learn until we added each other as Facebook friends. I don’t usually do that with dates until much later. But she mentioned it, and I ran with it. I wouldn’t have if I didn’t see a lot of potential in this one. Even more than Violet, Talia and possibly even Staci.

I know what you’re all thinking … he says that about all of them; “they have potential.” Well, they don’t make it this far if they don’t have potential. I don’t go on dates with them if I think they don’t have real potential. You don’t see the numerous women I have to go through and talk with before I find one to actually go out on a date with. As recent as this weekend, there were seven (7) girls on my radar that I was talking to off Match (texting or calling) – including Uma and Violet. Now, I’m down to only three (including Wanda), and I may not actually set dates with the other two, especially if things go well with Wanda.

She’s 5’9″ (about the perfect height for me), has a gorgeous smile and captivating brown-hazel eyes, and is just overall very beautiful. Quite possibly the most attractive woman I’ve dated, so far since I’ve been doing this site (but Talia is close, just a bit too short).

Back to the date … I showed up slightly before her and began checking out the place. Before long, she walked in and there was no mistaking it was her. It helps that she’s been sending me pictures just about every day (including today). We immediately hugged and made small talk as we checked out the store together. There was lots of brushing against each other and her standing in my personal space. There was also lots of laughter. After checking out the thousands of different soda brands, we finally settled on four very unique ones (including a chocolate covered maple smoked bacon soda) that we decided to sample together.

After purchasing our sodas (yes, of course I paid) we headed down the street to a local park where we sat next to each other on a bench in the shade. I grabbed my bottle opener out of my car, just in case they all weren’t twist tops. One by one we sampled them. I’d open them and hand them to her to drink first.  Then we would share the bottles, discussing the flavors, checking out the calories and ingredients. Though all the sodas were twist tops, and I didn’t need my bottle opener, they all weren’t easy to open. I even (unknowingly) cut my hand open. Neither of us noticed until I noticed blood on my shorts. It made for good conversation, and possibly a unique memory. Nothing like bleeding on a first date.

While sitting on the bench, she turned her body sideways on the bench to face me, and even put her leg behind (obviously touching me). When it seemed like she was actually rubbing her leg and foot against me, I put my hand on her leg to gauge her reaction. It didn’t phase her. No flinching, no pulling away, not even after nearly an hour like that. She also smiled a lot, not really at anything I said, but right at me while she was leaning in toward me. Almost like she was moving in for a kiss, but I can’t say for sure. I wasn’t about to try and be wrong. That will come tomorrow night.

The time for us to go came way too quickly. We both had to head home to pick up our kids from school. I walked her to her car and we talked about our plans for tomorrow night. Then we hugged – a lingering embrace, not just a quick hug – and she commented on how I smelled (and how she liked it).

We texted a bit back and forth tonight but nothing excessive. She still seems excited about seeing each other tomorrow night, even though it is going to be late (after 9 pm) and not very long (only 2 hours or so).

So we shall see how tomorrow goes. Check back for more updates, and as always … thanks for reading!

Update:  Since posting, her friend has an unscheduled medical procedure tomorrow (Thursday) morning, Wanda isn’t coming to town tonight, she’s coming in in the morning. So our follow-up date has been moved to next Thursday. Still being positive

Uma: Very intriguing vice principal, again making exceptions to the rules

Before my (supposed) date with Violet this Saturday, I met up with Uma.

I originally had Uma scheduled for Saturday night, but a work engagement came up that she didn’t feel she could miss, so we met prior to (both) her function and my (scheduled) date with Violet at Chili’s for a quick drink and appetizers – it was centrally located to both of us.

Uma is a local high school vice principal. She’s in her mid-40s, slightly above average height (not tall), blonde with a very nice body. Even in her baseball-sleeve length t-shirt, shorts and her hair pulled back in a pony tail, she still looked very attractive.

Now before you go bashing her dress code for our “first date”, keep in mind she just came from a function at her school where she was supervising a bicycle safety event being given to young kids. So she was dressed appropriately for that. We had discussed the attire beforehand, and I had no issues with her attire. So, to make her feel better, I was in shorts, t-shirt and a ball cap – dressing down for the occasion. But I still looked pretty good, though.

What makes Uma interesting is that, once again – as with Staci, I’m bending my normal rules to see how this goes. Yes, I hear the collective groan and the cries of “didn’t you learn anything from the last time?” But in fairness to Uma, I can’t blame her for Staci’s issues. However, she is never married, has no kids, and didn’t have a picture on her profile. All three of those things are pretty much instant disqualifiers for me. So why is she different?

She contacted me on Match with a very long, detailed explanation of why she was interested in me and why she thought we should get together and see how it goes (you’ll see this theme again shortly). She acknowledged not being married and not having kids because she was focused on her teaching career for so many years that she didn’t find time for those things. Now, she wants something more substantial. And as far as the picture goes (or lack thereof), she acknowledged that too. Because she’s in the position she’s in, she doesn’t want the possibility of people recognizing her online and having that interfere with her work. She had many pictures, and was more than willing to share them once we started talking. And yes, she looked like her pictures.

Before our date, we chatted and talked several times during the week, but definitely not as frequently as most other women I meet on Match. She definitely seemed more old school and independent, not needing to be attached to her phone and texting all the time. It was kind of refreshing. And for as little as talked, she always still seemed very interested in getting together and meeting. Emphasizing that she was going to make sure we got together before I left for the weekend and it was another two weeks before we could possibly see each other.

She happened to beat me to the restaurant, which never happens. I’m always early. But not this time. I was still early, according to when we said we’d meet, but she was there first. She had ordered appetizers and some drinks. I sat down across from her and we just started chatting away. We were there for a little over an hour, and it seriously flew by. We had great conversation but didn’t really get into anything overly personal. It was good, not awkward at all. I really think we hit it off.

Then when it came time to leave, she tried to pay. I halted that immediately because, well, it’s the gentlemanly thing to do. The guy always pays (at least for the like the first 100 dates or so). And I follow the code; opening doors, car doors, paying the check, not walking in front of her, walking between her and the street, stuff like that. Finally, I won the “battle” and she was very appreciative of the gesture, even commenting on it several times later.

I walked her to her car and we hugged as we talked about making plans for after I got back from my trip.

Things seem good. We’ve talked a couple of times since then. Everything still seems to be on track. But we’ll see. Based on recent history, I can’t count on anything (it seems) until it actually happens.

I’ll definitely keep you posted, and stay tuned later this week as something is brewing for Wednesday. And as always, thanks for reading!

Doubleheader weekend and more on deck

You know the whole “things happen for a reason” business, and the line about “when one door closes, another opens”? Staci who?

Ya, so true. It has been a crazy week. My Match profile has been blowing up this week. Granted, 75% of that has been your typical Match.com fake profiles, spam and scam accounts, which by the way is about ready to cause me to suspend my profle for a while to get away from all that. But I’ve had lots of prospects.

I had originally planned to see Uma (ok, my only 2 “U” name options were Uma and Ursula, what would you have done?) Saturday night. She’s an assistant principal at a local high school. Never married, no kids and her profile didn’t have a picture. Three strikes, right? But she contact me first with a very long, meaningful message and seems very interested in meeting me. We’ve talked over the past week a little, but she’s not like most girls on Match. I don’t hear from her very much, yet when I do she seems very interested. However, a work function came up for Saturday night so we’re going to meet for an hour or so Saturday for appetizers and drinks before her work function.

That opened the door for Violet on Saturday night. I am so relieved! I have really been wanting ask Violet out but didn’t have a window of opportunity any time soon, with my commitments with my son plus going out of town over Labor Day weekend. Violet and I have had a really good connection. She’s an accountant, mother of  4, fitness buff, blonde and gorgeous. But today, we were chatting and she mentioned she’d really like to see me tonight, even though our date is just tomorrow night. So i suggested we meet for drinks this afternoon before I picked my son up from school. She said she was just in workout clothes and had her hair up in a ponytail wearing a baseball hat. I said, “So?” She agreed and we met for a little over an hour. It was really good and fun. The conversation was great, she was beautiful even in her workout clothes, though I will admit she was a little heavier than I would’ve guessed from her pictures. But that didn’t bother, I thought she still looked great. So now we have the “first date” out of the way and we’ll see each other again tomorrow night.

Now, for those who routinely follow this page, you’re probably noticing that seeing Violet today throws my naming game off. True. But I had already decided on who was Uma and Violet before making plans today, so I’m sticking with it. Deal with it, you’ll get over it.

And ironically, one of these lady’s real name is actually one I used as a pseudonym for one of the girls recently posted on here. I really try to avoid using names I might actually run into.

There are also a few other developing options. One in particular I really hope develops into something, but she is a long-distance situation, which I really try to avoid. But again, she make a serious effort to contact me and sell herself why she was worth me making an exception to my distance “rule.” But we’ll see how that develops.

So please stay tuned for more updates, and as always, thanks for reading!

Talia: Date was great but my son is only 8

By now, everyone should be familiar with my naming game for my dates. I name them alphabetically (so we’re up to “T” since I started this thing) with random, false names to easily keep track and anonymous. And yes, I do have a master list of coinciding real names, but it isn’t stored electronically anywhere in case some Chinese or Iranian hacker wants to try to blackmail me someday.

This update features Talia, a name inspired by the fact that I was watching the Rocky marathon on TV when we were really starting to get to know each other. For those wondering how that ties with Rocky, well, Adrian – Rocky’s wife – is played by Talia Shire. Ok? Moving on.

Talia is about as close to being the opposite of Staci (and many of the other girls I’ve dated recently) as you can get without actually be a dude. She’s a nurse, only 5’4″, dark hair that she has slightly tinted with a redish-purple, busty, very expressive and communicative, and light-hearted. She had been married twice before and has a 24-year-old son and a 15-year-old daughter.

She contacted me on Match and we began talking. We really hit it off quickly and spent the first few days sending countless emails and texts, along with numerous phone calls asking all sorts of questions and talking about everything imaginable. We had SO much in common it was scary. We answered just about every basic question the same, with the exception of her liking fish and me hating it, and her favorite color was Orange … and mine isn’t.

We set up a date for Thursday because she was heading out of town Friday to spend the weekend with an old friend of her’s in San Diego as part of birthday celebration. Thursday was Talia’s birthday. She was insistent that we go out Thursday (on her birthday) because her deceased twin (who passed away 2 years ago in an accident) would want her to spend her birthday doing something with someone that would make her happy [1].

Things continued to develop very well up until Thursday. Lots of talking, texting and selfies. This girl had way too many selfies of herself, and she’d send me a few every day. I mean dozens that she sent me. She was gorgeous – don’t get me wrong – but I mean a bit too many selfies of yourself if you ask me. [2]

But in the meantime, I was a bit stressed out. I was struggling to find a babysitter for my son and was on the verge of having to cancel when one of my son’s friends’ parents (who knew of my situation) invited him along to a pool party they were going to. Yay, saved! So the date was on. I didn’t share these issues with Talia, by the way.

We met for dinner and immediately upon meeting she gave me a very intimate hug. I’m all for going for an introductory hug, if the moment feels right, but this was a bit intimate and lingered. [3] Dinner conversation was great! We talked about her interest in getting married again – she definitely wanted to, but I’m just open to the idea, that’s not my goal here. We talked about past relationships, and somehow we even had things in common with our past relationships and ex’s, so we understood where the other was coming from.

After dinner, since it was her birthday, I asked if there was anything particular she wanted to do for her birthday. She didn’t have any preference. So I mentioned we should just go have drinks at this bar I like to go to that has a rooftop bar with nice cozy couches and always has sports on the TV. She’s a big baseball fan, almost as much as I am. She would text me game updates and ask questions even when I didn’t have the game on. She was on top of it more than I was. Not a bad sign.

She thought that sounded perfect, even though I threw some alternate ideas out. At the bar, on the rooftop, we found a perfect sofa lounger with a perfect view of the game. We talked about random things as well as the game. That’s when she started telling me about this guy that strung her along and messed with her, she thought they were dating but he only thought they were just friends (with benefits). [4] She even mentioned that at some point, she is pretty sure she freaked him out [7], but she wouldn’t tell me how she thinks she freaked him out. So, even though I asked this once previously, I made sure she wasn’t still hung up on this guy. You can guess I’m a bit gunshy on the whole “hung up on ex’s” thing after Staci. She insisted she wasn’t and that it wouldn’t be a problem with us. She even clutched my hand (and didn’t let go the rest of the night) and snuggled closer after I brought that up, as a way of trying to ease my concern.

Well, that was until she mentioned “the other guy.” [5]

Right about the time we set up the date, she hid her profile on Match. She mentioned it to me because she said she wanted to “focus on getting to know” me. So after our discussion, I did the same thing. I really liked her and wanted to see where things were going, and I didn’t have any other serious conversations going on at the time.

Things were going so well, I brought up seeing her again and when she was available. Being a nurse, her schedule is very odd and whacked out. The next Thursday was about the only time I could realistically have a chance of seeing her because she was working lots of weekends and I am going to my brother’s over Labor Day weekend. So I said Thursday would have to do, because I wasn’t going to wait three weeks in between dates.

That’s when she brought up “the other guy.” She said that the day she met me on Match, another guy showed interest in her too, and she has been talking to both of us and she had a date set up with him on Monday (after she got back from San Diego). Needless to say that changed the tone of the whole date for the rest of the night (about the next 30-60 minutes). She insisted that she really liked me and wanted to see me again, but she was going out with this guy because she made the plans with him before she made up her mind about me and didn’t want to be rude and cancel.

Things tapered a little after that, and then around 9pm I said I needed to wrap things up because I had to go pick my son up from the sitter because it was a school night. She knew about the timing from the beginning, so this wasn’t a cop-out or anything. As we walked out, she grabbed my hand and we held hands as I walked her to her car. At her car, we said goodnight and kissed. However this wasn’t your typical first-date goodnight kiss. As soon as I went in for the kiss, she was clearly ready for it and it ended up being a long, deep, passionate type of kiss that lasted a while, not your normal easy, gentle, non-tongued kiss.

After we went our own ways, she texted me numerous times the rest of the night, just like everything was cool. But it clearly wasn’t.

Starting the next day, things clearly started falling apart. I hardly heard from her Friday.[6] I texted a few times to see if she was on her way, etc. Her responses were short and non-engaging. She said she would let me know when she landed in San Diego. She never did. I texted her later that night just to say “I hope you’re having a good time.” I’m guessing some of you are wondering why I was being kind of clingy with her about it. Well, she mentioned early on that she likes to know that her guy is thinking about her and likes to hear from him every once in a while. So I was just trying to make sure I didn’t give the impression I wasn’t interested. But I definitely wasn’t overdoing it.

Saturday was more of the same. I hardly heard from here. And when I did, it was in response to my text and it wasn’t very engaging either. Short, quick responses, then nothing for several hours (meaning like 5-6 hours). I wasn’t sweating it, but I was noting it. I was totally intending to give her her space to enjoy her time with her friend, while also still trying to maintain a level of interest with her.

Sunday was a little better. She communicated a lot more on Sunday, and actually let me know when she got back home. However I did notice she never responded to my question about Thursday. Earlier in the day,I asked her about Thursday again because I needed to make sure I could secure a sitter for Thursday. But I got no answer. After she got home, we chatted for a little bit, and I told her that after she got settled in, and had time later, we should talk about her trip because I wanted to hear how it went. I’m very partial to San Diego after living there for more than 6 years, so I wanted to hear what she did and where they went.

That’s when I got the text message saying she didn’t think we were a match. She thought I was a great guy and everything, but she doesn’t want to date anyone with kids younger than her’s. That may sound a bit odd and selfish, but to her credit, she DID have that written in her Match profile, so it’s not like it was some out of the blue thing. However, remember, SHE contacted me first on Match, and my profile also clearly states that I have an 8-year-old son that lives with me full-time.

And that was that. Just like that, it was over. In retrospect, I shouldn’t be surprised. I mean, if you go back and look at the highlighted numbers (i.e. [1] ) you’ll see some of the warning signs that I noticed immediately and let pass, or that caught my attention later.

Moving on.

And I’ve been getting some questions asking if I have heard anything from Staci yet. NO, I have not. It’s only been a week people. I told you, after a month, maybe two, she’ll realize what a bad idea getting back with this guy was. But the more I think about it, the more I think I won’t hear from her again, and the less I think I want to. So again, moving on!

I hope you all have a good week, and as always thanks for reading! Please share this site with your friends and readers on your own blog.

Staci: Hoping making exceptions to the rules pays off

Over time, I have established a pretty standard list of criteria/rules to follow when meeting people online. Some things are your standard dating rules, while others are based on my personal experiences or preferences.

Some of those are ones like: no sex on a first date, she can’t be taller than me, I won’t date a woman my age who has not been married before and/or doesn’t have kids, I won’t even entertain talking to a woman who is only “separated”, and a few more.

But with Staci, I saw enough potential with her that I went against my normal practice and made a few exceptions hoping that it would pay off. We shall see.

First, a little about Staci. She’s a tall (5’11”), very skinny, blonde, who is a little older than me (45), and she works as an investment broker. She’s been divorced for about 4 years and doesn’t have any children, though she did have a stepson who visited while she was married.

Our email and text conversations were very fulfilling, fun and even flirty. Some nights we’d be up until midnight chatting away. She would text some during the day, would text when she got home in the evening, and when she would go out with her friends to happy hour or something, she wouldeven text me once she got home. It seemed pretty obvious that she was interested in me more than just a simple curiosity or feeler that I get from some of the other dates I’ve met online. This seemed to be mainly why I was willing to skip some of the normal rules I follow when dating women online.

Now let me break this down by explaining some of the exceptions I made to my normal rules. The first was the rule about Not Going to Movies on the First Date. But that is what she wanted to do. She wanted to see Entourage badly, and I really couldn’t say no to her. I was hesitant about seeing a movie on the first date, and she knew that, because I mentioned it would limit our time to be able to talk and get to know each other. Something told me she knew that, and it wasn’t going to be a problem and maybe she wanted to be “alone in the dark” together. Since we were going to one of the newer, fancier theaters that has the super nice recliners and bar inside the theater, we decided to meet at the theater bar about 90 minutes before the movie.

We had a couple of drinks at the bar, talked about many things, including my previous marriages, my kids, her previous marriage, and even sports since we both like baseball and the Stanley Cups Finals and UFC were on the TVs at the bar. We laughed and even flirted a little. She looked incredible. There wasn’t any question about whether I was physically attracted to her.

Once we got into the theater, we took our reserved seats. They were large leather recliners paired together with a raisable center arm to convert into love seat, if you chose to. We ordered some snacks to eat during the movie. During the show, there was definitely a physical tension between us, like we were like magnets too close to each other. So midway through the movie, I made a move. I had debated it for a while, so I just placed my hand on her leg, palm up, looking to hold her hand. She quickly grabbed my hand. Not only did she hold my hand, but she would occasionally stroke one of my fingers with hers, and eventually grasped my hand with both hands. This is clearly not a sign of someone who was just going along with my move in order to avert an awkward moment, she was clearly ok and accepting of it.

After the movie, she wanted to linger there in the seats for a while, talking for a bit longer while still holding hands. It started to get a little awkward, only because we were the only ones in the theater and the theater staff was cleaning around us. So we headed out to the parking lot. We were parked on opposite ends of the lot, so I walked with her to her car. On the way, she grabbed my arm and we walked arm-in-arm for a while, and then we held hands all the way to her car. There we lingered for a while talking. Finally, I just grabbed her and pulled her in for a kiss. Again, there was no sign of awkwardness or resistance. We paused a few times, only to resume again. She even wrapped both of her arms around my neck, drawing me closer. The kissing itself, may not have been the best I’ve ever had, but I chalk that up to the awkwardness of the first kiss.

We said our goodbyes and talked about when we would see each other again. It wouldn’t be the next weekend, because was going out of town for the weekend with her girlfriends. We even talked for a while after we each got home. Everything seemed to go very well. It was seemingly one of the best connections I’ve had in a while.

Now to the second rule I looked past in order to give Staci a chance, and this is the one I’m more concerned about.

As I said earlier, she’s in her mid-forties without kids. Why, exactly, I don’t know. I didn’t ask (yet). But she is always going out with friends, either to happy hour, sporting events, concerts, or whatever else is going on. Since I started talking to her, she’s been home all night, on average, about 1 or 2 times per week. There’s nothing completely wrong with that, she can do whatever she chooses, it is just a matter of compatibility with my schedule. The first time she wanted to hang out was a random weeknight and I had to say ‘no’ because I had my son and no options for someone to watch him on such late notice.

And that is why I have the rule about Not Dating Women Who Don’t Have Children. They don’t fully understand the issues parents empathize with each other. They usually don’t understand the difficulties with having to plan dates, instead of being able to up and go out on a whim. From personal experience, I’ve had many instances where childless women get jealous, impatient, and frustrated having to work around a single father’s schedule. Especially one as sporadic as mine.

We haven’t talked about it yet, but I can see it has the potential to be an issue. And then there’s the issue of the following night.

The next day, things seemed different. Almost like they do when you have a one-night stand – and one of you regrets it the next day. But based on her actions, there was no sign of any hesitation, so I am not sure what it could be exactly. Except for one thing.

She mentioned she was going to a concert that night, and was very vague about her plans that day and evening. We talked much, much, less than normal, but she did still ask about my son’s baseball game. However, unlike other nights out, I didn’t hear from her during the evening or after. I sent a couple quick messages, saying I hope she had fun, etc. I also sent a quick “good morning” text the next morning. Only got a quick “Thank you” response and nothing more after that. So my guess is she was on another date.

Not that it bothers me, I totally get it, I do the same thing – at least the overlapping multiple first dates until you establish a connection with someone. Then I cut off things with the others, or it fizzles out on its own.

And I’ll be completely honest, to me, if I’m overlapping dates, I try to keep things as “normal” with each one as I can – if I am interested in keeping each option open. But if I’m not, I will cut it off and not drag it out knowing it is not going to work. I would just ask the same from them. At least “act normal” until you make up your mind. Because now, I’m more likely to keep my eyes open looking for other options, which could make for very awkward times if she ever decided to actually see where this goes.

But don’t worry, I’ll keep you updated. Keep checking back for updates. And as always, thanks for reading!

p.s. Oh by the way, even though she really hasn’t been talking with me lately, she’s been checking out my Match profile every day or even several times a day. So, there’s that.

UPDATES

Second date success, but something’s jamming my radar.

Making Strides But The Big Test Could Be Right Around the Corner

She said Yes to the weekend getaway

Weekend road trip was great, despite no sex

Dinner at her place, I’m meeting her best friend

Dinner, meeting her best friend not what I was expecting

Staci, Amy wanted me to go out with their friend tonight – alone

Hot and Heavy but not quite a Homerun yet

Mountain out of Molehill and She cancelled again

A Great Day, A Shot to the Heart, then Sexting

Touching all the bases, but still no home run

I’m pretty freaking devastated right now

She meets him on Tuesday and small test may be coming

The Writing is on the Wall but still playing the waiting game

Tuesday (and Staci) are gone with the wind