Should I Approach Him First?

Back in seventh grade, I used to know this guy from an exchange. We became friends but lost touch once the program was over and never talked again for the last five years.

Lately, I’ve seen him in town a couple of times (nothing but eye contact) and soon after at a club where he was super nervous but actually came up to talk to me. We had a really awkward chat, and he tried to compliment me, told a couple of silly jokes and everything but didn’t ask me for my number. Even though I suggested having coffee some time, he didn’t message me on Facebook so I did, and the response was poor or at least not what I had expected after that night.

Another night we ran into each other at a bar, and he was again just staring at me without saying a word but appearing out of nowhere everywhere I went, even in front of the ladies room! A friend of his, who he must have told about me because we clearly don’t know each other, recognized me saying he knew me from school, and he tried to keep up a conversation with the three of us. It wasn’t until they almost left that the guy talked to me, and it was something really random. Yet, I saw him blush and become really nervous.

But again, he didn’t message me or anything. A couple of days ago, I saw him in town and he clearly saw me too, but I got so embarrassed about the fact that he may or may not have already rejected me that I looked away the moment he was coming closer, so he just walked by.

So what is this about? Does he like me or was it just the usual initial interest in someone you haven’t seen in a while? Should I “accidentally” run into him again (as I know where to go now) and approach him first this time? Thanks for reading, any help is appreciated!”

-Gigi K. (Pennsylvania)

Hi, Gigi. Thanks for your letter.

There are a couple of things that don’t quite seem to fit, but for the most part, this seems like a pretty straight-forward case of a shy, socially awkward guy with a major crush on a girl he considers to be out of his league. How you handle it depends on how badly you want to date this guy or at least how much you want to figure out what’s going on with him. Since you wrote the letter, let’s assume there is some curiosity/interest there for you.

I don’t know if this student was on a foreign exchange program or just exchanging from another area school. In any case, he may feel like an outsider, especially if he was dropped into the middle of suburban WASPville from a Jewish school, an Islamic upbringing, or a country with very different social standards regarding dating. By our standards, he is bound to seem a bit immature in the relationship game.

My intuition also tells me you are most likely a quite pretty, reasonably popular girl with a down-to-earth, easy-going nature and sweetness about you. You probably befriended him in the seventh grade at a time when he felt nervous and alone, and he probably was drawn to your approachability and friendliness.

But five years have passed, and it’s time for him to grow up. Go ahead and approach him. Let him feel safe, but let him know your losing your patience a little bit and you don’t understand his mixed signals. Tell him that every time you start to get interested in him, he flakes out and makes you feel like he doesn’t care. Is he interested in dating you? If he is, he doesn’t need to have a friend approach you, and he should at least send a nice text that doesn’t make you feel rejected. Tell him the things you think are sweet about him, and invite him to coffee. Make him give you an answer right now. If you don’t really want to date him, let him know that, too. You can still be his friend and help him to become a more confident man.

If my assumptions are off base, write back and we’ll keep working on it!

Nick