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!

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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

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