Datehazard’s Blog

On dating, singleness and adjusting to being 30ish.

The Dating Tutor February 21, 2009

Sometimes, when you don’t know what you’re doing, you need to talk to someone who’s been there, done that.

Like one of these fictional ladies.

Been There, Done That

And that’s exactly what I did last night. I ended up having a 3.5 hour conversation with my friend The Toronto Journalist. We haven’t spoken in months, and I figured it was time to give him a call. Especially since he’s from New York and lived here for most of his life.

The hours flew by and I dished to him about my most recent adventures, and my current fixation with The Charmer. He, in turn, told me about his current dating woes and the problems he’s having with his long-term girlfriend, The Box. The Box works in the medical field, and she Does Not Like Many Things. She’s also apparently super-private.

When The Toronto Journalist told me he’d never even met The Box’s friends, in the 1.5 years that they’ve been together, I was shocked. The Box liked to tell my friend, by way of explanation, “I’m sorry, but I’m just a private person.” Uh… Ok?

She also does not like taking photographs, and until The Journalist maneuvered her into a compromising situation (friendly to normal photography), with her brother and her family members’ help, he did not have a single photo of her. When he’d try to explain to her that it was important to him to be able to see her face while at work, or just to have a memento of her while she wasn’t around, she would reply, “Well, you can always just see me in person.”

Trouble in paradise. I’ll keep my fingers crossed.

Meanwhile, he gave me the same advice I’d been giving myself: when it comes to The Charmer, the only way for me to be in this situation is to step back and see what he does next. If he’s really interested, he’ll let me know.

And he gave me an earful of information about men in New York City — the way most of them do indeed play the Seduction Game and string women along, and that most New York women understand this and also have their own game of manipulation. He did say, though, that when these men recognize or realise that they’re dealing with women who aren’t from the city, they usually drop their game and try to be real.

I wonder if it’s really that easy. I mean, if you always play a game, it becomes second nature. You don’t even know you’re still doing it.

Meanwhile I really do have to tell Corporate Lawyer that I am no longer dating just him. I know he’s dating around, and assumes I am too, but that doesn’t mean I have no responsibility to him.

And Non-Profit Guy and I are going to a play today. Purely as friends. In that “WTF??” way. I will keep you posted.

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Possibly Probably making a mistake February 16, 2009

The Charmer called. We made plans to meet up tomorrow, at his swanky apartment profiled in a major international newspaper (he was also quoted in the same article). I have to give it to him, he is a smooth operator. This is how it went.

“Hey DH, how’s it going? How are you doing, sweetie?”

“I’m fine, TC, much better now that I’m hearing from you — I’d been waiting for your promised call this morning. How are you? How’s work going? I’m glad you managed to finally squeeze some time away.”

“Well, it’s really busy since the acquisition of the other company late last year. Then at the same time that deal was being negotiated, we decided to expand operations into another country. Then my Dad had a health problem, so I was at one point in the hospital, with my mom and dad arguing in the background while I was trying to talk to the lawyers to negotiate both deals. You can’t make this stuff up.” (laughs).

“Yikes. Is your Dad doing ok? What happened?”

“Oh he’s better now. He’d had a quadruple bypass and they found out that his arteries were really clogged, so he had a choice of having to do another quadruple bypass or having stents put in. So he opted for the stents, which is why he was in the hospital for some time.”

“I’m glad to hear he’s better.” Pause. “I’m wondering if I could talk to you about your text message about meeting up.”

“Yeah… (laughs). I figured you probably thought it was a weird message, and a strange way to have a first date. I can assure you that I don’t always arrange first dates like that, but because this week is so packed and I want to spend some time with you and figure out whether we can get along, I felt like I had to send a direct message like that. But I really don’t do stuff like that.” (Laughs).

“I figured it was something to that effect. I mean, I also checked the time of your text message, and figured from your subsequent one that you were probably a little drunk when you sent it, so you probably didn’t intend for it to have quite the bluntness that it did.”

“Yeah, well, no, it wasn’t just that I was drunk, it was because I wasn’t sure how to fit all of these things together. But yeah, I probably would have phrased it somewhere along the lines of, ‘you know, I don’t often do this, and I hope it doesn’t make you uncomfortable, but how do you feel about…'”

We both laughed. Ha ha ha.

“So, I figure we could meet up tomorrow, I’ll get my car service to pick you up and bring you here, and we can have a carpet picnic or whatever, maybe I’ll get a DVD and we can watch something.”

“Uh… Well, where do you live? I mean, I could easily take the train there. The trains run all night, right? How far away from the station are you?”

“Nah, don’t worry about it. I’ll give you my address, I’ll just arrange for the car service. It’s really no problem at all.”

“And by the way, I don’t want to have you think I would stay overnight and you’d have to drive me in to town the next morning. Let’s leave that possibility open and see what happens.”

“Oh, no, really, you’ll see, I’m a perfect gentleman. I have an extra bedroom and everything, so if you want to stay there, that’s perfectly fine with me; if not, whatever — there’s no pressure at all. Seriously, I want to make sure you’re comfortable.”

I hate to say it, but he’s smooth.

He continued, “But I would suggest you might want to pack an overnight bag; I mean, just in case you stay. It’s also more convenient so you can have your stuff with you if you need it.”

The guy is seriously amusing me.

What the hell. I’ll give it a go. There are lots of horrible worst-case scenarios, but I don’t think many of them will apply to this situation. And I am seriously entertained by this guy’s shenanigans!