As in all things, timing is everything when it comes to online dating. People enter into the dating arena at all stages of relationship readiness and sometimes you don’t find out until it is too late that the guy you are interested in has no business being out in the dating world. This was the case with Leigh, my next date, who should have come with a sign that said ‘emotionally unavailable’ hanging around his neck. I was not, however, so lucky as to get a warning so I was forced to find out the hard way.

Leigh showed up in my daily email of suggested guys from Match.com and, after clicking on his profile, I found myself pretty interested. He was cute, owned his own real estate business and seemed to have a solid base of friends and family in the Seattle area. After my last date (a poor actor with questionable role choices), Leigh sounded alluringly stable and safe. I couldn’t tell yet how exciting he was but I was intrigued enough to send him a short email.

It was clear from our first contact that Leigh was totally, totally new to online dating. He asked me on our second round of messages what the whole ‘story’ was and what the ‘rules’ were so that he didn’t mess them up. I assured him that I didn’t believe in the whole ‘Swingers’ mentality of waiting a specific amount of days to call or initiate contact but rather that it should be easy and comfortable and not so rigid. This seemed to calm Leigh down a little but I could tell he was still just…scared and uncomfortable about the whole thing. We started emailing right before Thanksgiving but he seemed to disappear over the long weekend and I thought he had run off into the hills in fright. A week after the holiday, though, he tentatively reached out and I all but forced him to come and meet me for a drink. Some days, it seems, you have to try a little harder than others.

Leigh and I agreed to meet at a bar located between our two neighborhoods. He sent me an email the afternoon before our date to tell me that, watch out!, he had met with two clients that day and consumed two lattes so he was wired for sound. Things could get crazy! I have been warned of a lot of things but this was new. Hopped up or not, I was excited to finally get to meet Leigh.

As over-caffeinated as he might have been, I was fine with Leigh almost immediately. He was very nice, almost bland nice, had a decent sense of humor, was easy to be around and, once his drink kicked in, he wasn’t at all too amped. I asked about the spelling of his name since it was a tad unusual and he said that he was ‘named after Jerry Lee Lewis’. I took a sip of my drink so I didn’t blurt out that, what the hell?!?, those names are totally spelled differently, but Leigh beat me to it. He laughed and said, “I know. My parents had half of a good idea.” It was comments like that which made me like Leigh. He seemed all kinds of vanilla but then he dropped something like that out of nowhere. I was getting the slightest bit charmed.

I sensed trouble, though, when we started talking about the adventure that is online dating. Leigh’s whole demeanor totally changed and it was so, so clear that he did not want to talk about that subject at all. I didn’t want to be a jerk but such a visceral reaction had to have some story behind it. I insisted that we get another drink to buy myself time to figure Leigh out.

Leigh turned out to be a bit of a lightweight – apparently caffeine was not all he was sensitive to – and the story came crashing out midway through our second cocktail. Leigh had had the awful misfortune of recently getting out of a long relationship with a woman he thought he was going to marry but had turned out to be all kinds of mentally unstable. He looked like he was going to cry as he sat there, gripping his drink, and told me about the horrible time he had been through trying to end their relationship. Wonderful – I was going to be responsible for causing my date to have an emotional breakdown just to satisfy my sick curiosity. But, really, it wasn’t sick. I had some sort of right to know where he was at, right? Right?

Thinking fast, I recommended that we hold off on more drinks but rather get some chocolate cake instead. If sugar was the third stimulant in Leigh’s trifecta of chemical instability I was in for it but, thank you thank you, he seemed to get in a better mood. By the time we finished our cake, served with the coolest little milk jug that we both had to take pictures of ourselves with, I was feeling the slightest little crush on Leigh. Maybe it was ok that he was a little unstable and on the mend and maybe he just needed the guidance of a good girl like me. Danger, danger, danger, those thoughts.

As I drove home I wondered if Leigh was going to be ready for whatever the next step was in whatever type of dating thing we had going on but I need not have concerned myself. Mother Nature was deciding for us. Not two days after our first meeting, Seattle was hit with a huge snowstorm (for Seattle) and the city shut down. I was stranded at home for a few days, as was Leigh, and, without him, I am not sure I would have gotten through it. We sent each other fun emails through the day and spent what felt like hours on the phone comparing the food in our pantries to see who would starve to death first. But, really, all we talked about was snow and the weather. It did not get more serious than that.

The snow melted before we perished but then it was Christmas and then New Year’s and, before I knew it, it had been almost a month since I had met Leigh. It seemed like we both knew either the timing or the chemistry was just not right for us. I suggested, finally, that we meet for dinner and a movie in January and it was enjoyable and we even held hands and kissed but something was just…not…there. I am not sure if I was turned off by the hesitancy on Leigh’s behalf or we just didn’t have a spark and a click but, after that date, I just was not that thrilled at the idea of doing it again.

I didn’t hear from Leigh for a few months (apparently we felt the same way about our chances in love), but I did get an email from him asking if I was still dating and available and, if so, would I be willing to meet him for some video games and pool? I will admit that I got kind of excited at that email and, after agreeing to his offer, at the thought of meeting up with him again after a little bit of time. Maybe the months apart had been good for Leigh and he had been able to move on from his ex-girlfriend. A girl could hope. I was waiting in front of the pool hall and Leigh drove by in his brand-new, pimped-out Cadillac, waving. The guy could definitely make me laugh.

My hopes about Relationship 2.0 were soon dashed, though, after we got some food and drinks and hit the arcade. I just still felt unsure about Leigh. He was laughing and seemingly having a good time but there was just something distant and kind of awkward in everything we did. After about 45 minutes I just really wanted to go home. A date, in my mind, should not feel so forced. All of the signs were telling me that, no matter how much I hoped it might work out, it was just not in the stars for Leigh and me.

I did get an email from Leigh almost a year later, oddly enough, to tell me how much he loved my blog about online dating. He had even been at a party where they took turns reading my entries out loud. That blew my mind just the littlest bit but I was glad that, even though we weren’t meant to be in love, at least we could still be cool with each other. Through the wonders of Facebook I know that Leigh has gotten married and seems to be, from what I can tell, a pretty happy guy. I still have the picture of Leigh on my phone, eating chocolate cake, drinking his milk and looking all kinds of not ready to be in love with me. Even though it was disappointing at the time, I am glad it was just me he was not ready for.


Just a reminder: I am going to be starting an online dating themed podcast in the next couple of weeks and I would love your stories, questions or advice to include in the show. Send them to dateswithkate@gmail.com!

Published in: Uncategorized on October 31, 2011 at 3:30 am  Comments (1)  

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One CommentLeave a comment

  1. From now on, I’m gonna try and sum up Kate’s date experience in 5 words or less so you won’t have to read through all that stuff, kind of a condensed Cliff notes. This one is easy:

    Leigh – Drives a Cadillac – Next!

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