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 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

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!

Constance: Started so well, then POOF it was over (Rewind)

This Rewind post will be more of a relationship synopsis instead of just a date review.

Constance, as the C name would suggest, is the third attempt at dating this year as I start this single-dad dating thing.

Clearly, since we went out, things on Match worked out well enough for us to see each other in person. So we set up a date a local Mongolian barbecue place that I love. When she showed up, she looked pretty much as advertised in her profile pictures, except she was wearing glasses, but that was nothing to dwell on. She was real tall for girls that I date, she was 5’10” without shoes, so with shoes she was really close to my height (6’2″). But she was dressed very very casual, wearing jeans, tennis shoes and the female equivalent of a t-shirt. It wasn’t as bad as Hermione, but still, I was dressed well for the occasion.

The date went really well, conversation was good, we shared some good stories and then went to a bar for some drinks after dinner. She told me about the time she went on a date with a guy from Match who looked nothing like his profile picture, and when she asked him about it he said “you wouldn’t have gone out with me if you knew what I really looked like.” Duh, but falsifying yourself is so much better, right? After that date he went in for the kiss and she dodged the bullet, but then he asked for a ride home because someone dropped him off for the date. She said no and went to her car. Waiting to see what the guy did before she tried to leave, she noticed him cross the parking lot and get into a car and drive off. Creepy!!

Anyways .. moving on. Things went really well and we saw each other a few more times. There really seemed to be a strong connection developing.

Then it all fell apart in (literally) an instant.

I was hanging out at her house after she made me dinner and we were sitting around the kitchen table drinking beers and chatting. That’s when I mentioned – in passing as part of the conversation – that early on after my divorce when I wasn’t seeing anyone I would let me ex-wife stay at the house when she was in town visiting our son. She slept in his room every time and nothing ever happened between us. I was, and still am, NOT attracted to her anymore. She is such an ugly person inside that it doesn’t matter to me what she looks like, I’ll never be able to sleep with her again. Too much baggage and drama with her.

That’s when Constance flipped. She literally snapped. She got all upset and went on about if that was her ex, she wouldn’t be able to resist sleeping with him and that it wasn’t ok for her to be staying there. Keep in mind this all happened long before I met Constance, and there was no chance she would be staying at my house anytime soon. I kept trying to assure her that if she didn’t like it, it wouldn’t happen if we were still dating the next time my ex-wife came into town. That didn’t matter.

The “argument” spilled over into the next day over text messages. I repeatedly tried to make her see that it happened long before her and I knew each other and wouldn’t happen if we were still together the next time she was in town. She kept on going on about how I was obviously choosing my ex-wife over her. What?? How is that? How is something I did months previous, and NOT actively doing, translated into me choosing my ex over her? I said I would totally understand, that if my ex came into town and I let her stay at my house while Constance and I were still dating, her getting all mad at me for that . That would be understandable.

I kept trying to make her realize that she was making a big deal about something that wasn’t real, something that hasn’t actually happened, hoping she would see she was overreacting and let it go. But after about 20 minutes of texting all of this back and forth, she finally said “Don’t ever text me again!”

OK. Done. And I haven’t heard from since.

Things started off so well and then, BAM, she flipped and it was over. It was the strangest “relationship” I’ve had in a long while.

Sorry this update isn’t as detailed as the others. But it has been so long since this all took place, I didn’t want to bog down the story. If I wanted to grade the first date, like I’ve been doing, I would’ve given it an A-/B+, but after things ended it would totally skew my opinion of the whole thing.

Back to your regular programming, citizens.

Christmas Eve ramblings and updates

Merry Christmas and Happy Holidays to everyone!

Since I’m sitting at my parent’s house (totally bored) alone with my sons are with their mothers this year, I figured I’d catch you all up on how things are going.

I told you I pretty much put dating on hold over the Holidays, so … of course, what happens? Yep, multiple interests come seeking me out. Never fails.

I seriously contemplate just forgetting about actively dating because when I ignore the “dating game” prospects just come to me (somehow).

I’ve had two serious prospects over the last week or so. Both contacted me on Match and I’ve been talking with both since. Naomi, is a petite, 40-something CPA, mother of 3; and Olive is my age, a classic country girl with a son about the same age as my youngest son.

Things with Naomi were a little too aggressive and moved a bit too fast. We’d been taking for about a week when I took my son to his mom’s. She was very aggressive in saying how much she was thinking about me and talking about plans and stuff already. This is all before we’ve even met yet. So on my way back from dropping my son off, she called and we talked almost the entire 4-hour trip back. Then she basically invited herself over to meet me at my house when I got home (about 1 a.m.).

We both had to work the next day, but I figured “what the hell, why not?” She met me near my house and followed me home. Honestly, once we got to my place, I figured we’d chat for a while and she’d go home. I was wrong. I grabbed us both some water in the kitchen when she came in and grabbed me and started making out with me. She dragged me to the couch for some more making out, then suggested we go upstairs to the bedroom.

Ok. This was moving a bot way too fast for something that would have any chance of being a serious relationship. But I’m a guy, it’s not like I’m gonna really say NO and stop things. My chances at this are too far and few between.

After a vigorous round of bedroom aerobics, she stayed and cuddled til we both fell asleep. She stayed until about 5 a.m., when she got up to leave and get ready for work. All the next day she texted and called repeatedly. Over the next few days, the conversations trailed because she was becoming too clingy and we hadn’t even really gone a date yet. I was getting highly annoyed, and just couldn’t take it much more. So I told her I wasn’t sure things were working out, maybe we should slow it down a bit and see what happens. It’s been a few days and I haven’t heard from her since.

I haven’t met Olive yet, in person, but we talk every day. She’s very sweet and we have so much in common and our little boys seem almost identical. So far, if there’s a problem of any kind, it’s that our schedules have been seriously conflicting so we haven’t been able it meet yet. It’s not a serious issue since we’ve only been trying for about a week to find a time. But she had her son when I was free and now that he’s visiting his father’s, I’m visiting my family out of town.

But as I’ve been writing this, Olive has been texting me the whole time because she’s bored bad wants me to keep her company.

I am a little paranoid about dragging this out about another week or so, because the last time this happened, coincidentally over the Christmas break, the girl I was into moved on (back to her ex-husband) before I really even had a chance.

But I guess, as they say, “things happen for a reason.” Maybe this one will work out better than that one.

I’m going to sign off for now. “It’s A Wonderful Life” and a 24 hours of “A Christmas Story” are on.

Merry Christmas and Happy Holidays to you all, and thanks again for reading.

Mona: Baseball mom knocks it out of the park

Hello everyone. I’m writing this tonight, even though my attention span is being pulled in lots of directions with homework, my son, and flipping between Monday Night Football and baseball games. But I wanted to get this knocked out while it was all fresh in my mind.

Background: Mona contacted me a while ago on Match, but I really didn’t pursue her until just recently. When she first contacted me, there were lots of other things going on: Justine just ended, things with Krystal just started, I started talking to Lola, and then there was the whole Winky thing.

Even though she was very attractive in her profile pictures, she had very little written in her profile so there wasn’t a lot to go on. But as things unfolded with the other ladies, she always managed to stay on the fringe. If you know anything about Match, there are several ways to indicate your interest without actually writing a message. I guess keeping her female pride in tact, she exhausted all of those options over the course of a few weeks without actually breaking down and messaging me.

So, finally, I dropped her a line to say “Hi”, and I must say it was one of more shorter, yet more clever introductory emails. I hate this part of online dating. The Dreaded First Contact Email, especially when Match makes you use a stupid Subject line. She mentioned being a single mom drowning in an ocean of Barbies. My message played off that, being a single parent with a boy with an army of action figures carpeting my house. That, and the fact that we are big baseball fans, was all it took to getting things rolling quickly.

She is 42 with a 21-year-old son who plays competitive amateur baseball, and she loves baseball and football. She also has two younger daughters, 4 & 6. She’s about 5’8″ with great brown eyes, naturally wavy brown hair, and a terrific, fit but not muscular, body (from what I could tell). I got a good initial hug, and there was no cause for any concern.

She gave me her phone number in her initial response because she isn’t sure how much longer she wants to hang around Match (a very very common sentiment these days). So we started texting and talking within hours of that and things have been rolling very nicely.

The Date: As you know, I’ve been a proponent of the “quickie date” recently after too many questionable experiences. Couple that with my crazy schedule, and spending time with Lola, I really don’t know when my next free “date night” will be. So I suggested a lunch date with Mona near her work. She thought that was a great idea and we met today at a restaurant near her office, which is about an hour from my house.

She showed up in a very lovely form-fitting white blouse with jeans that fit perfectly. She looked just like her pictures, but in person that feels so much better. Like I said, we exchanged a very nice hug and she seemed very excited for the date. She had seemed rather excited for it over the last few days, even while she was out of town celebrating her son’s 21st birthday. So things were off to a very good start.

For the hour we were together, we talked mostly about our kids. I felt like I had a constant smile on my face, and looked the same way. We were so focused on each other we nearly forgot to order lunch. The servers were very understanding and patient with us. We were showing each other pictures of our kids like a couple of grandparents showing off their grandkids, and she even moved over to my side of the booth and sat real close to me showing me videos of her son playing baseball.

As it was happening, her sitting that close to me seemed like a very big deal (a good sign), but then the pessimistic side of my brain started downplaying it like it was no big. What do you think? A good sign or not a big deal?

She even commented how impressed she was that I kept my phone in my pocket the whole time, except when we were sharing pictures, because some guys she had recently been out with had their phones out and were paying attention to them instead of paying attention to her.

Idiots!! Even if I had my phone on the table, I wouldn’t have touched it,  because I was so into her. She’s so beautiful and engaging, any guy paying attention to anything else doesn’t deserve a girl like that.

The hour went by way too fast. She had to go because she had a client to meet with. We could have easily spent another hour there just talking. It was very easy and natural.

I walked her to her car and we just kept talking, both of still with smiles on our faces. We both agreed that we need to find a time very soon to get together again for a “real” date with more time together.

Post Date: Since the date actually took place this afternoon, I don’t have a lot of “post date” information for you. I texted her on my way home thanking her for the date and telling her what a good time I had and that I really wanted to get together again. She concurred and we talked about everything from looking like our profile pictures to watching the football and baseball games on TV tonight.

I know I’ve had a few good dates recently. But since January this has to clearly be the best. Yes, the date was good, but the conversations, the things we talk about, the things we have in common, etc., make it a lot more than just a good date. Plus she even fits what I have been looking for physically.

In regards to potential, she has the most of any of them so far (since Abigail). So much, that I would easily consider deleting all of my dating site profiles in a heartbeat if she asked. Of course that is something that won’t be addressed for a while yet, but I’m just sayin’.

However, my pessimistic side is creeping up again, leading me to think this is going to go more like Ellen. She seemed to be a complete packaged deal with lots of potential, but just faded away after the first date and nothing ever amounted from it. Call me overly pessimistic, but that’s the way it is sometimes.

Grade: A (could be a +, we’ll see)

Speed Dating: Just my random thoughts hitting all sorts of things

I had a lot of thoughts running through my head on things to update you all on, but I didn’t want to write a new post for each individual one. So I figured I would knock them all out here.

First, things with Lola have lots of potential. We’ve hung out a few times and have a great time together every time. We haven’t had what I would call our official second date yet, since we have only hung out together for an hour or two just to spend some time together having lunch together or something. No, we haven’t had sex yet. Is that all you people think about?

Speaking of sex; things with Krystal are fading out, and fast. She recently started a new job so I haven’t had the same exposure to her that I normally had. But she is very clingy and a little intrusive. She’s always telling me she misses me, and has even been asking to come to my son’s baseball games and come over after he goes to bed at night. I’ve had to shut her down more times in the past week than I would ever care to.

We also had to have “The Talk: Deuce” because after the initial version of “The Talk” some things started coming out that I wasn’t really cool with. When this whole thing started, I was under the impression this was just going to be a fun FWB thing, and that her husband was cool with it. Well … apparently he doesn’t know about me as much as I was led to believe. She says he is rather naive and clueless and has no idea of what she is doing. She isn’t happy in her marriage and doesn’t leave because of the kids. She told me earlier that she was “happily married and in love with her husband” several times. So, the tapestry is unraveling. And now I’m not as comfortable with this as I once was. This is definitely a different scenario than what I signed up for in the beginning, and I thought I was pretty blunt and honest with her as to what I was looking for. She wants to get together next week after I get back from my long family weekend trip to Texas. I am not really interested and kind of dreading it. Especially with thing going well with Lola and the possibility of another upcoming date (with Miley). I think it’s about time to end this bad MTV reality show I’m living in. I’m not desperate enough to need sex that bad to need to hold on to this arrangement.

And remember, I told you that my luck would change once I started down this Ashley Madison-inspired trail. First Lola comes along right as things with Krystal and I get started, and then Miley, with whom I’ve had only 2 messages with previously, comes jumping back into the picture, after a few weeks of nothing. So I figured I’d at least have a quickie date with her for lunch or something to see how things look. I don’t juggle girls very well, so I’m not really interested in dating multiple girls at the same time, but I guess I can’t also dismiss one without at least checking it out first. You never know what might happen. All the more reason to get rid of my clingy, married, side piece.

Lastly, I am still looking for any feedback or suggestions on what you guys would like to see from me on here. Any additions, topics, whatever. You name it and I’ll consider it.

Thanks for reading and have a great Labor Day weekend.

Lola: I took a shot and hit the target

Background: Lola is another one of my Match dates. She didn’t send me any messages or winks, but she liked a few of my photos. So I checked out her profile, liked what I read and saw, and decided I’d just send her a note thanking her for admiring my photos and just made some small talk. She responded, and we started talking from there.

She was ending her time on Match after only about 2 months because she was having to block too many guys, hide her profile too often and was even thinking of changing her phone number because of all the creeps she’d been meeting online. This has been a broken record lately, talking with girls who are fed up with sites like Match because the guys are too creepy, inappropriate or over-aggressive.

We’d been emailing back and forth for a few days until her paid account expired, then she gave me her personal email and things were going very well. I took a little extra time before offering up texting and calling each other because I didn’t want to seem like I was just like all the other guys she was talking to. Even though I got a sense that she didn’t think of me that way, I still didn’t want to push my luck.

But I did NOT want to play myself into the FriendZone. So I offered up my phone number and things took off from there. No hesitation on her part to text me, or call me, so things were looking pretty solid.

So after a couple of weeks of talking/chatting, I finally had a free night coming up and we set up a date. She’s a hairdresser and has a unique schedule where she has alternating weekends off, and has Mondays and Tuesdays off. She usually doesn’t have Fridays off, so she took a vacation day so we could go out Friday night.

A little about Lola: She’s tall (5’11”) – which is a weakness of mine, attractive, in her low-40s (just a bit older than me), never been married and doesn’t have any kids of her own. But she’s very much a family person, loves kids and is very involved with her nieces and nephews. I haven’t asked about the “no kids” thing yet because that is kind of a sensitive issue. Maybe she can’t for some reason and I don’t want to broach that subject too soon, especially since having kids is not any sort of priority for either of us (her profile listed that she didn’t want kids but it was ok if her partner had kids).

I kicked around some new and different ideas for our first date. I thought about taking her to a baseball game just to do something a little non-traditional, otherwise we’d just do the typical dinner and dancing idea (since she mentioned she likes to dress up and guys don’t take her anywhere which requires her to dress up). So I came up with a very non-traditional choice, but wouldn’t tell her what it was, trying to keep things interesting. I let her know what she should wear (casual clothes), but that’s really all I would let on.

The Date: Based on where we were going and our time constraints because I had to drop my son off at his friend’s house, she agreed to drive to me because it would take about 2 hours for me to drive out to get her and come all the way back. Thanks to rush-hour traffic, it took quite a bit longer for her to get to my house than originally planned, but it wasn’t a big deal.

I was so relieved when she finally got out of her car that she looked like her pictures and like she described herself. She was tall, slender and very cute. We were already leaving many of my previous dates in the dust at this point, and we’d barely said “Hello” yet.

We chatted as I drove to our initial date location, but I still didn’t tell her where we were going. As I turned down the street to our destination, I asked her if she had ever fired a gun before. She replied with much more excitement than I expected, “Is that where we’re going?” When I responded affirmatively, she was so excited.

At this point, I figured the rest of the night would go smooth, because I thought this was the “make or break” moment. Either she would hate the idea and the date would suck, or she would love it and the date would go great. Thank goodness it was the latter. I had also read in numerous places that taking a date to a gun range can really get the endorphins flowing.

It worked like a charm. I gave her some instructions on how to hold, aim and fire a handgun. Of course this meant plenty of opportunities to get close and touch her. That really seemed to break the ice so much faster. And we had to get real close to talk to each either, too, since it was so loud inside the range.

I could see the surge rushing through her after she fired off her first shot. I let her fire about 75% of the shots, since I’ve fired countless numbers of rounds in all of my years in the military. I would step in every once in a while to fire a few rounds when she needed a break because her hands and arms were getting tired. I helped with more instruction, gave her advice, and helped spot her shots so she knew where she was hitting the target. For a beginner, she was doing outstanding. She would generally hit the target within a 3-inch radius of where she was aiming and was keeping her shots in tight groups. That is something military and law enforcement practice hard at being able to achieve. She was a natural.

I expected to only be there about an hour, but almost 2 hours later, we decided to head to dinner even though she would’ve stayed longer to fire more since she was having so much fun. We even kept the targets so she could have them as souvenirs and take them home. I even took pictures and video of her so she could have them all to show her friends and family. She really appreciated that and couldn’t wait to show the girls at her salon.

The next stop was a live music spot in my part of town that I had been wanting to check out for a while. It is supposed to be a jazz/blues club, but also has bands that play some rock as well. It is also billed as one of the top local barbecue joints in the area.

We got there after 9 p.m. and found a nice spot up near the front. The place was almost at capacity but there were a few open tables. We ordered a few beers and the barbecue sample combo. The food was outstanding, but still took second place to Lola.

We had such good, easy conversation while we ate and listened to a local 3-piece blues/rock band. We had lots of laughs and never ran out of anything to talk about. I found ways to talk mainly about her and her career, and stuff like that. I am not much about talking about myself. Time flew by. We even managed to find ways to continue to casually touch each other – always a very good sign on a date. The next thing we realized, it was about 11:30 p.m.

As we were getting ready to leave, I apologized for making our first date so loud so we basically had to yell at each other all night just to have a conversation. She laughed it off and we decided to go somewhere much more quiet to talk for a little bit longer. So we headed to my place for another beer or two and talk.

At my place, we cracked open a couple of beers and talked for a little while longer. I had a been a fairly good boy to this point in the night, and decided I need to make my intentions known and made my move for the kiss. After that, everything was glorious. It was great. We made out for a little while – kept our clothes on the whole time (in case you were wondering) – and then sometime after 1 a.m. I suggested it would probably be a good idea if she went home before things got into some dangerous area.

I walked her to her car, gave her directions how to get back to the highway (since I had to walk her in to my place earlier), and we kissed a bit more. As always, I made sure she let me know when she got home. About 2 a.m. she texted me she was home and we exchanged a few more messages before going to bed. Things were looking very promising.

Post date: Like I said, things are looking very promising. We’ve been talking all day and have even planned another “date” for Monday afternoon, since she doesn’t work and I don’t have class.  I want to make sure I see her again this week because next weekend I will be out of town for Labor Day weekend and won’t be able to see her for almost 2 weeks.

Now, I have to figure out what this means with the whole Krystal situation. She was constantly texting me last night during the date, but I was ignoring them because I think it’s rude to keep checking your phone on a date. I have to check to see who it is, in case it is an emergency or something with my son, but if it is someone else, I ignore it and don’t respond. And all that did was make it worse because I was ignoring her. Ugh.

Grade: A

Thanks for reading and stay tuned for more!