Dear Captain Awkward,
I’ve got a thing for this guy who I met through a mutual friend. He lives in another city so I don’t see him all that often [it’s close enough that a lot of people date (and non-romantically commute) between the two cities, but far enough that casual hanging out with friends can be difficult]. We’re fairly friendly on Facebook and the like though, which has kept the infatuation going.
Mutual Friend thinks we’d be perfect together, but she refuses to find out if he might be interested in me [because she is also awkward?]. I’ve reached the point where the fun of having a crush has worn off and normally at this stage I’d just go ‘fuck it’ and get a good friendship out of the deal – but that is probably why I am perpetually single with a lot of really amazing friends. I feel like I should be proactive about this and actually do something, but my issues with that are as follows:
- I’m not sure that it would be a good idea to start something with this guy as Mutual Friend is really important to both of us and it would add an extra level of awful if things went wrong [basically the ‘But what if our friendship is ruined!’ excuse, but with an extra person].
- As I don’t actually see him very often I may have built him up too much in the ‘Oo, crushes are fun!’ stage, breaking rule #2 of the Rules for Geek Dating and increasing my levels of intense awkwardness.Case in point, I am writing a multi-paragraph letter to an advice column about a guy I hardly know.
- I’ve got no idea when I’m going to see him next, but it is probably not for awhile, which means if I am going to do something it will need to be over the internet.
So my questions to you are:
Should I go for this? It seems like really flimsy grounds to possibly start a lot of drama on.
If I do go for this, is there a way to indicate your interest to someone via Facebook message without it being super weird? Particularly someone who you’ve never hung out with one on one? I’m one bad day away from sending a message that reads “HEY I THINK YOU ARE GREAT AND MAYBE WE COULD HANG OUT SOMETIME BECAUSE THAT WOULD BE GREAT, BUT IF YOU DON’T WANT TO THEN THAT IS GREAT TOO AND WE CAN JUST PRETEND THIS NEVER HAPPENED. K THX BYE.” And that would not be attractive to anyone.
Hello, you didn’t pick a snappy nickname, so I’ll pick one for you:
DEAR OVERTHINKING IT:
There is a reason your mutual friend will not “find out if he likes you” – it’s because you are all over the age of 15, yes? So (s)he is generally encouraging, but wants to stay out of the middle and wants you to handle stuff yourself. That seems like a pretty great idea and not awkward at all. But where does that leave you? It leaves you just asking him out already. Here you go:
Option 1: ”Dear ____, can I buy you dinner next time you are in town? I’d really love to hang out with you.“
Option 2: ”Dear ____, I’m going to be in (your town) the weekend of (date). Can I buy you dinner or brunch one of those days?“
I know, I know, it feels like there is so much at stake, but I refuse to believe that any friendship, including the one with your mutual friend, is so fragile that it cannot handle that question. I can’t remember the last time I dated without using the internet as a go-between, but in the olden times I think people met each other through other cool people they know and having friends in common was a reason in favor of a relationship, not a reason to avoid one.
If he says no, the distance is actually an advantage, because a lot of time will go by until the next time you see him and the awkwardness will wear off with time. Then you’ll run into him via your mutual friend, and you’ll look all cool and unapproachable and gorgeous. He’ll say “Hey” and you’ll say “Hey” and then you’ll ask him a question about something totally unrelated to show that you’ve let it go, and it will never come up again. If by some unlikely fluke he avoids you forever, then you have just found out that he is a Giant Rude Awkwardpants and you didn’t want to date him anyway.