Datehazard’s Blog

On dating, singleness and adjusting to being 30ish.

Back on the dating scene (again) March 10, 2009

Tonight I’m going out for date #2 with The Analyst (same guy I had the Best First Date Ever with). We’re going to meet at a public monument, then meander and figure out what we’d like to do. Basically take it easy and wander around. It sounds like a lovely way to spend an evening with someone.

I know this will sound like I’m jumping the gun a little bit, but I’m not sure whether The Analyst and I have all that much chemistry. When we spoke on the phone last night, he was really hesitant and quiet. It made me think about the fact that I thought he seemed pretty depressed when I first met him. I mean, he laughed at all my jokes, and he seemed to really appreciate my sense of humour, but it seemed to be because he was really in a sad space and needed cheer, rather than that he was really genuinely appreciative. There wasn’t the witty back-and-forth or the one-upmanship that one would expect from someone who was really following.

Then there’s another guy who I’m meeting up with on Friday: let’s call him Hedge Fund Trader. Yes, yet another finance guy. He is hilarious and sarcastic, and seems pretty high-energy. We’ve been texting back-and-forth, and the jokes keep flying. I haven’t yet met him, so I can’t tell for sure, but he also seems like he might be a bit self-centred and maybe a touch of an asshole. The kind who would do something to someone else and not apologize, because as far as he’s concerned, it was funny/amusing. And his opinion is all that matters in this situation. He reminds me a bit of my good friend the Computer Programmer, who would also never intentionally set out to hurt someone, but who also has that “I’ll do what I want, thank you,” attitude, at times. We’ll see what happens.

In the meantime, the Charmer called. He called yesterday, and we had a brief conversation. He sounded guarded in his language and mannerisms, but said he’d like to meet up. He wasn’t sure about timing for this week, but wants me to text or call on Wednesday or Thursday in case he can meet up.

I spoke with my friend Kind Ninja (yes, she really is that fantastic), and I told her about how I’d reacted to The Charmer and everything that happened. She told me that she thinks I should just follow my heart and seize my desire with both hands. I said that I really just didn’t want to be heartbroken — that the problem I have with the Charmer is that my reason and logic are completely overtaken by a kind of senseless desire when it comes to him. And that I have no idea what to do with those emotions, let alone how to handle it if things go badly.

And then she said the sweetest thing to me that I have possibly ever heard: she said, “DH, listen to me. If things don’t go well and you’re heartbroken, I will come to you, and I will pick you up. Really.”

I am so lucky to have a friend like her in my life.

And today, I am feeling happy and confident, and optimistic.

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Meeting the friends & family March 1, 2009

Filed under: Adjusting,Dating — datehazard @ 11:38 pm
Tags: , , , , , , , , , ,

Last night, I met up with the Corporate Lawyer, his sister, his visiting lawyer friend, and her two married friends (another corporate lawyer, and an architect).

We had dinner at a delicious restaurant, and I got very drunk while we were waiting for our table. It took a while for them to get our table ready, eventhough we had a reservation, and Corporate Lawyer and myself were the first people to arrive. The drink I had at the bar, on an empty stomach, went right to my head. Fortunately, the drunkenness really came into full force during the serving of the main course, and no one seemed to notice.

Meanwhile, Corporate Lawyer had been particularly agitated that day, and told me that he was really worried that he was going to get the axe at work. He’d read one of his partner’s actions as a sign that his performance was not considered up to snuff. It didn’t sound that way to me, but I’m not sure if there was more information he was withholding, and didn’t press for details. He was miserable enough as it was. At one point, he said to me, “well, DH, I guess you’re going to be the only breadwinner soon.”

I laughed at him and gave him a hug to cheer him up.

Don’t get me wrong, we’re still not dating exclusively, and I still get the “I’m not sure I’m that into you” vibe from him, but he’s starting to open up a little more to me. Which is, frankly, neither a good nor a bad thing.

Call me opportunistic or just plain lazy — or most likely both — but I just don’t really care about this relationship. He has a lot on his plate, as do I, and I’m perfectly happy to coast for now. Especially after the drama of The Charmer. It’s nice to hang out (and occasionally make out) with someone who’s pretty undemanding, pleasant company, and pretty straightforward. I keep thinking that we should be having a serious conversation about Where This Is Going, but last time I checked (about a week ago), he was totally uncomfortable with anything serious, and told me that he was happy with how things were. Which I clarified as that we’re dating other people. The only thing I asked for was that he would tell me if/when he slept with someone else, for my own health’s sake. We’re both cautious and safe people, but I’d rather minimize my risk whenever possible.

So, I guess there’s nothing to worry about?

I’m not looking to date anyone else right now. Should I be? Should I hedge my bets?

This is starting to feel like work…