Trinity: She said Yes, then said Goodbye*

Hello everyone,

I know it has been quite a while since you last heard from me. I’ve been rather busy; still trying to find a job, recovering from hand surgery, and spending a lot of quality time with an amazing woman, Trinity, whom I asked to share my life with.

I haven’t been posting about her because I felt like I might jinx things if I share them here online. But I guess that doesn’t seem to be much of an issue now. I’ll try to keep this as short as I can and update your more on her and our time together later.

Things with Trinity, as I’ll call her for numerous reasons, were going great up until about a week ago. I asked her to marry me in July and we were planning a wedding for early Spring next year. We had our wedding and reception venues reserved, and were going to book our hotel guest room contract. We had sent out the “Save the Date” notices to our friends and family. I was on cloud nine with her.

Then a week ago Thursday (10 days ago) she called me before going to bed (as she did every night) after her regular Thursday night dinner with her best friend. Out of the blue, she told me she was feeling very stressed about all of the wedding plans, to include our finances because of my lack of a job currently and her lack of income from a rental property she hasn’t had filled for months, along with other personal concerns. She said she felt rushed a little and wanted to postpone the wedding date for a while until we had things established a little better. I was totally supportive and had even told her that I had considered that us getting married next Summer right after school restarted would probably be a much better time to get married.

You see, she wanted to incorporate all of our children in the ceremony and my son gets back from visiting his mother for the summer in mid August right before school stats.

Everything had been OK since then, but she was still acting a little weird. And I was still adjusting to the news. You can’t expect her to drop news like that on me without it bothering me a little bit. Though I was supportive and understanding, the fact that the change was bothering me didn’t set well with her. And then my normal joking, flirty ways – that she originally fell madly in love with – began to annoy her. It seemed I couldn’t say much of anything substantial (especially something related to my feelings) without her getting upset or irritated.

Then Friday (2 days ago) we met for lunch and discussed things further. I started feeling much better after our talk, because she was reassuring me that she still loved me, I still made her happy, and her goal of marrying me and spending our lives together has not changed. We spent the rest of the day texting like normal. Then after her kids went to bed, she called me and dropped the bomb on me.

None of it really makes sense. Yes, we had bumps in the road just like everybody else. Yes, she likes to shut down when she gets stressed and isn’t the best communicator. But none of the issues were remotely close to “relationship killers”, hell, not even the sum total of the issues were enough to terminate a serious relationship like this.

This issues definitely seemed to be the stress of combining our households and her maintaining her free time, and a few smaller issues which we had dealt with early on that seemed to linger. But again, nothing that couldn’t be resolved or worked out.

I tried reassuring her that the wedding plans were not the priority – that her happiness was – but she insisted I was just saying that, but wouldn’t give me the chance to prove it. And several of her “issues” were easily explained away or remedied, but she made sure to say that it wasn’t going to change her mind. She finally ended it by saying she was going to return the ring to me. I reiterated that it didn’t have to be this way and we deserved more of a shot than this.

Since Friday, I have not heard from her (as I’ve mentioned). I’ve desperately wanted to hear her voice or just tell her the usual nonsensical things that transpired in my day. I’ve had to fight from texting her good morning or calling her before bed every day.

Everyone I’ve talked to says I just need to give her some time and space. If I try to reach out too soon, it will just make things worse and push her farther away. I definitely don’t want that. I hope they’re right. But it doesn’t make it any easier.

How much time? How long do I have to wait before I can reach out to her?

She still hasn’t removed me or my family and friends from her Facebook. If you knew her, you would know how serious keeping her Facebook private is to her. She only has about 35 friends and family on Facebook. She’s been on Facebook numerous times since Friday night, so if she was going to do that I figure she would’ve done it by now. I can’t help but hold onto that as a small glimmer of hope that she isn’t fully committed to terminating our relationship.

And though everyone is telling me that I will hear from her and she might come back, because they all saw how great we were together and can’t imagine someone throwing it away so hastily. I sure hope they’re right, but I’m not getting my hopes up and am doubtful I will hear from her anytime soon. That’s why I have the asterisk (*) in the headline.

I’ll definitely keep you all updated on things as they transpire – if anything does happen. In the meantime, if you have any specific questions you want me to address about in my next posts, or if you have any comments or suggestions, please feel free to drop me a line. I’m especially curious to know if any of you have taken “a break” like this and how long it lasted.

And as always, thank you all for reading!

Advertisements

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!

Bella: We have all the time in the world

Following our great breakfast date, Bella spent the day working at the salon.

Now here’s the dilemma I have when she’s at work, she’s very busy with all of her regulars who will wait up to an hour just to have her cut their hair. She has almost no time to take a break or even eat lunch most days. And she asks me to send her text messages regularly because she likes to see messages from me while at work, but she rarely, if ever, has time to respond. The problem is that it is difficult to come up with stuff to say throughout the day when she doesn’t respond. It’s like coming up with one-liner after one-liner all day.

I want it to be clever and witty, and I just don’t want to say “I’m thinking about you”, or something lame like that, all day. It’s kind of stressful. But I do my best.

So Friday after she got home from work, I went to her place for a relaxing night of watching movies. She had to get up early to be at work Saturday morning for an 11-hour day at work.

I showed up while she was still getting ready after showering. She left the front door unlocked for me. So I let myself in and began setting up the movie and drinks that I brought for us. Shortly, she joined me downstairs in the kitchen while she made her dinner. We embraced and kissed for nearly the entire time her food was cooking.

Bella is clearly more demonstrative about her interest and affections for me than Ariel ever was. Which, in hindsight, reflects what I should have been reading during my time with Ariel. Bella shows her interest much  more, in how she is with me in person as well as when we’re away. Bella is already starting to use “pet names” like “babe” and “baby”, and actually compliments me. Ariel never complimented me – except once to tell me I smelled good – or ever used any sort of “pet name” or term of endearment.

We spent the evening with her wrapped in my arms, drinking cocktails and watching “The Best of Me” (yes, the same Nicholas Sparks movie Ariel wanted to see) – it was totally Bella’s choice. Of course, there was kissing – lots of kissing. But knowing she had to get up so early for such a long day, along with the fact that I was going to see her again Saturday night, I/we didn’t push the issue even though the sexual tension was very high.

I left a little after midnight as she was heading off to bed.

Saturday, however didn’t go as originally planned. She spent most of the day keeping me updated on the situation with her youngest son’s father. He hadn’t picked up his son all weekend (which starts on Thursday for him) from the father’s parents where her son was currently staying. So she had to pick him up from her ex-in-laws after she got off work.

Our plans weren’t cancelled but seriously altered. I had purchased her a simple rose bouquet for Valentine’s Day – which neither one of us really celebrates. But I definitely wanted to express my appreciation for her. So I just went over to her house for about an hour to give her the flowers and spend a little time with her.

She was already in her pajamas sitting on the couch eating dinner when I arrived. Her son  was already asleep. She was very grateful for her flowers. And we spent the short time I was there snuggling on the couch again, of course kissing again. She snuggled in very close and I stroked her hair, and she actually fell asleep on me twice. So we called the night short so she could go to bed.

The best part was when I was preparing to go and we started kissing again and she jumped up and wrapped her legs around my waist as she passionately and intently kissed me. The urge to carry her upstairs like that and take her to bed was difficult to fight. But that would have to wait for another night.

As we walked to the door, she apologized for having to cut the night short, hoped that I wouldn’t be mad at her for altering our plans, and offered to come stop by in between her split-shift at work Monday since I live rather close to her salon. I told her I understood, that these things happen and there was no way I could be mad at her for something like that.

That’s when she said, “Plus, we’ve got all the time in the world to see each other.” That simple comment meant so much, as she clearly meant she plans to see a lot of me and doesn’t plan on going anywhere.

Sunday I drove through bad weather to get my son (nearly a 10-hour day) while she worked nearly the same amount of time and then had to go get her boys. We didn’t talk much during the day, as I was driving in bad weather and she was working. So I asked her to call me once the boys went to bed. The last I heard from her was she was snuggling in bed with the boys watching cartoons. She never did get around to calling. She fell asleep watching cartoons with them.

Then, this morning, she informed me that her oldest son woke up with an ear ache and her youngest had a bad cough. So her mom took her oldest boy to the doctor where he got antibiotics for his ear. She never officially cancelled our time together, but I was pretty clear we weren’t going to see each other today. She decided not to work her afternoon shift so she could get the boys, after going to the gym, and take them home. I held out hope that she might decide to just swing by for a minute to say Hi. But it didn’t happen.

She hung out at her mom’s for a few hours before going home. On her way home, she said she missed me (for the first time). And SHE said it first. Once, again, that simple comment lifted all of the dark clouds that had been building during the day.

As of now, we don’t have any plans for seeing each other this week or weekend – yet. She has Tuesdays off but has her kids all day, so I’m almost certain she will stop by before work Wednesday and will see her Friday night. She has her oldest son Saturday night after work.

But I will definitely keep you all informed what happens next. And please, follow me on Twitter for more live updates, comments and posts. To get post updates, please click the “Follow” button to the right. Or post your comments and questions below.

And as always, thank you 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!

Ariel: I Made Her BFF Cry

For starters, I was going to wait until tomorrow to post an update on things with Ariel, but changes in circumstances have freed me up to write an update today.

She called a bit ago to tell me she’s sick – “throwing up sick”. However, she has not officially cancelled all of our plans, she just wants to see how she feels and sounds optimistic we’ll still see each other tonight. However, it remains to be seen how much of our plans remain in tact. We were originally going to watch “The Best of Me” (Nicholas Sparks, chick flick), I was going to make chicken flatbread pizzas (she doesn’t like red meat) and then watch the Super Bowl together.

So, on with the update.

This week was full of major dating milestones. I picked her up at her office for lunch earlier in the week. She invited me up to her office to meet her friends/co-workers. We even waited around for her cubemate to get back from lunch so I could especially meet her. That’s a pretty big step. Intentionally introducing me to friends and co-workers isn’t something you do with just some casual date. Sure, it happens when you might run into someone you know while you’re out on a date, but this was intentional. To top it off, the first thing she did once we stepped into her office was kiss me, a serious kiss not just a peck. That surprised me somewhat. After the last time I dropped her off at her office and she was a little concerned about showing too much PDA at the office, I never expected to kiss her there, I figured that would wait until we go to the car. So that was another pleasant surprise.

After we had lunch and she returned to her office, she was texting that all of her co-workers we all raving about me. Several of them even commented on how good I smelled – which was literally the first thing Ariel said when we first met. They asked what I wore because they wished their men smelled that good. I refused to share my secret and told her I didn’t want other guys walking around smelling like me, especially ones she knew. Playfully of course.

Ariel is not a very flirty, or complimentary. She doesn’t use pet names or anything like that, or even say “babe or baby”. That’s totally fine. Which is why when she does say things like she’s excited to see me the next time, or calls me wonderful, or whatever, it really resonates. She’s not like others who jump into things like “I love you” too early.

Things all week were very positive, nothing questionable. Conversations and texts were solid, fun and enjoyable. She even called me one night because she was working on the Match profile for her good friend’s 22-year-old son. OK, ya, I was like why is a 22-year-old on Match? Turns out he’s a little nerdy (plays video games and Magic the Gathering) and has never been kissed (or had sex obviously) at age 22. So he’s trying to find somebody. So she asked me for help and advice on putting his profile together. First thing, this kid’s expectations were out of whack. In his present state, he’s looking for a 20-something supermodel. OK, who isn’t? Dial down the expectations into the realistic zone there, son. I thought that was a positive sign, involving me in this thing she was doing.

Then Friday, we were going out with her best friend in the world, Darma. No pressure at all, right? She had plans for Saturday with all of her sisters and girlfriends coming over to her house, so Friday was my night.

We met up at this quaint little place they both like to frequent. We talked about everything from my son, my military background and even that I am a gun guy. Darma was just so enthralled, continuous saying that her fiance and I would get along so well. They were making plans for us all to go to their favorite winery together, among other plans for all of us – like date nights at the range.

At one point, Ariel dismissed herself to go to the bathroom. You know, the old “I’m leaving for the friend to ask the tough questions” routine. As soon as Ariel was out of ear-shot, Darma started in. They were all pretty tame and straightforward, I didn’t have any problems with answering them. We even discussed how my ex-wife and Ariel’s ex-husband are so similar, and how Darma “hates” her ex. The only question I struggled with was the question about my feelings for Ariel. I didn’t want to say too much, but wanted to definitely convey I was very interested in her. I was in the middle of trying to explain something when Ariel returned, so we stopped in the middle.

You see, the majority of people who know me (friends, family and colleagues) will refer to me frequently using such words as stoic, robot, emotionless, and intimidating because I don’t talk a lot and am very quiet. Now, I have no problem socializing, but I’m generally very quiet. I warned Ariel about this from day one. However, I haven’t shut up from the moment I met her. People also know I never smile. I always hear complaints about pictures because I will smirk, but never smile. But my face hurts after all the smiling I do around her. She just brings that out of me. I can’t explain it any better than that.

So a little while later, Ariel brought up my not talking and not smiling, playfully calling me a liar because she has no idea what I’m talking about because she’s never seen this side of me. I even warned her I’d probably be nervous and quiet around Darma. Again, I wasn’t. So I playfully jabbed back about airing all of my business out to her friend the first time she met me.

That’s when Darma asked me about me allegedly being quiet and not smiling. I told her I could provide a laundry list of people who could back up my story, especially my ex-wife (who to this day attacks me for never showing her much affection when we were together, but I didn’t tell her that part) who could easily confirm I’m an emotionless robot, and never smile.

Then she asked me to explain why I’m not that way now. As we discussed it, I basically repeated something to the effect of “I don’t know, I really can’t explain it” while subtly pointing at, or glancing at Ariel while I said, to suggest it has something to do with how I feel when I’m around her. I really wish I could recall exactly how the conversation went in order to properly convey it.

But when the conversation was over, she was in tears – good tears. We wrapped up dinner and went our separate ways. Darma gave me a big hug and said she was glad to meet me and we’ll all have to get together soon. I think I passed the BFF test.

After, we went to see “The Choice” (yes another Nicholas Sparks chick flick) and then back to her house. It had to be an early night because she had a major workout session early Saturday morning at the gym.

I was fully intending to just walk her to her door and head home, I didn’t want to try to push things when she made it clear she needed to go to bed early. But she invited me in for a while. We talked for a while and I checked out her paintings. She’s a painter, a very good one. I was really impressed.

But then we started kissing heavily. After a while, I suggested that I wasn’t going to leave, she was going to have to kick me out if she wanted me to go. We kissed more. Again, I said, look if I don’t leave soon, we’re going to be up very late and she wouldn’t be happy in the morning. We kissed even more. However, I was looking for any sort of sign for something more, but never got it. No suggestive touching, no leaning, angling or moving back toward the bedroom, and definitely no more overt gestures of grabbing my hand and leading me in that direction. As much as I wanted to drag her into the bedroom, I just couldn’t help but think it wasn’t the right time and definitely didn’t want to spoil things by moving too fast for her.

That brings us to today. Last night, she had her friends over and she was up past midnight drinking Crystal Light vodkas (dangerous) and eating pizza (regular pizza, not healthy pizza), which both seem to be the contributing factors to her feeling ill. I know it all too well. Once I started eating healthier, any fast food or junk food (especially KFC) made me feel totally ill.

And I don’t think she’s using it as an excuse not to see me. I know some people do that. But she at least called me to tell me and explain, so I could hear her voice as she told me. Not just texting it. She’s also called a few times to update me. She still talks as though she’s hoping to better so I can come over at some point. If she was just trying to use it as an excuse to cancel, she would’ve cancelled right away.

So hopefully today is not a total loss. I bought all the supplies for dinner tonight and a few other things, and would hate to see all of that go to waste. She definitely sounds like she feels genuinely bad for altering our plans. I’m not too upset, but I am definitely disappointed.

Our next scheduled time together is next Saturday, but I’m sure we’ll see each other at least once before then, probably for lunch during the week. And if she does cancel tonight, I get the feeling she’ll ask to make it up to me tomorrow night.

I’ll keep you posted. I guess it’s a good thing I posted today and didn’t wait until tomorrow. This was long enough.

And, as always, Thanks for reading!!

p.s. please follow along on Twitter as I will post some more causal updates along the way, instead of waiting for a big post update like this.

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