Survey the District: How Can I Make Concrete Plans?

Dear Date the District,

I met a friend of a friend a couple of weeks ago, and he invited me to his birthday party the night after we met. I was tentative about being able to make it, so I told him I was busy. He fell of the face of the earth for a few days, and then the next Saturday around 5, told me he was going to a specific bar that night, and wanting to know if I had plans. A friend of mine from college was in town, and I had plans with her. Again, we texted back and forth a bit. Fast forward to this Friday, and I get a text from him in the afternoon, asking what I'm up to that night. I told him I was going out with co-workers and where we'd be, also asking what he's up to that night. No response, but text again this morning, saying he fell asleep early but he's going out to Fenway tonight and to let him know if I wanted to meet up for a drink. I suggested a bar, since I was going to a party there later that night, and he wrote back saying that he has to be in Fenway for a friend's birthday so he can't come to Cambridge. And then I ended up saying that I'm probably not going out because my dinner plans were running late and I'm kind of tired, and we texted back and forth again a bit. The past few weeks, our text conversations ended with things like "yes, let's hang out next week" but not this time, instead talking about something about our mutual friend.

So the real dilemma is that this has turned into this stalemate, with neither of us wanting to budge--I don't really like playing by his "you can come meet me where I am" rules, and the lack of notice. I feel slightly awkward going to a bar and meeting all his friends (since I'd have to gather a bunch of my friends too, which is not that easy to do on like 4 hours notice). I'm pretty busy, and I don't want him to think that I don't want to hang out with him, and I don't like feeling guilty about having to constantly say no, but I'm not really sure how to express this to him. Really--I'd just want to get coffee and chat with him for an hour. Should I just suggest that outright? Thoughts? 

This problem comes up a lot when you meet someone new—guy or girl, friend or potential love interest. Once you’ve been living in a city for a while, you have friend groups, haunts, habits, and it’s hard to figure out where this new guy will fit in.

You’re right to avoid going to a bar alone to meet up with a group of his friends. That’s just begging for things to get awkward, for you to get clingy, and for him to feel like he has to entertain you when he might want to talk to his friends. Plus there’s the fact that when guys go out with their friends, they tend to get wasted, and nothing ruins things like watching him puke and rally.

The ideal situation would be to bring a group of your friends to meet up with a group of his friends. But it can be hard to pull a group together so last minute, and even harder to convince your friends to venture out of their neighborhoods (plus, doesn’t the T close at like 9 p.m. these days?).

You’re doing the right things so far. You’re busy, and you’re not dropping everything to spend a few minutes with him. Which shows him that you have a life, that you have tons of people who want to hang out with you, and, most importantly, that you’re not desperate. This is probably why he keeps texting you—if you’re so awesome that you have plans every night of the week, who wouldn’t want in on that?

It’s great that he suggested meeting up for a drink before he went out. And it’s great that you suggested a bar on your turf. Make him come to you, so that he feels like he has to work for your company (and appreciates it all the more when he gets it).

Keep things going in this vein. If he suggested a drink before, he’ll probably bring it up again, and maybe this time you can suggest a place that’s a little closer to his side of the river (without venturing into the territory that celebrates Evacuation Day).

But don’t text him and ask him to get a cup of coffee. That’s asking him out, which we never advocate because it makes you look super available, and super interested (which is super not sexy).

Guys usually don’t agonize about this stuff as much as girls do. So definitely don’t verbalize (or textualize) your guilt about not being able to hang out with him. Like we said before, your unavailability is probably part of the appeal—wanting something he feels like he can’t have.

He’s probably not obsessing over why you’re busy, and if you show him that you are, you’re also admitting that you spend a lot of time thinking about him.

If he wants it badly enough, he’ll head over to the People’s Republic of Cambridge. And the only way you’re going to inspire that kind of lust is by keeping up what you’re doing—living your life, and letting him adjust his schedule accordingly.