A Word of Advice... on friends... or more?

By Joshua O'Connell
Posted Monday, June 11, 2007

I met this guy on the internet. After talking to him for a while and getting to know him a little, he started asking me to meet up with him. I was scared so I kept making up excuses. He kept telling me I was pretty and stuff. So finally I went to meet him at the club. I brought my friends, and he brought his. We ended up hitting it off so good that we were cuddling in the booth at the club.

The night ended, and we went our separate ways. We still talked on the net and occasionally on the phone, but he hasn't brought anything up about what he thought of me in person and if he wants to take it any further. I haven't asked him because I don't think it's my place to make a move. In any case, I like him a lot and would love to get to know him better. Maybe get into a relationship down the road. But I'm confused. I don't know what I should do to get the ball rolling.

--Confused club cutie

Cutie, you’ve done well here. You met a guy online, you were cautious, brought your friends, things went well, and connections were made. But you seem conflicted. On the one hand, you don’t want to make a move because you feel it’s not your place. On the other, you wonder how to get the ball rolling. So, here’s my advice…

MAKE YOUR MOVE! Let’s consider the risks. The potential upside: you form a friendship with this guy, potentially even a relationship. The downside: he loses interest (or you do, for that matter) and you part ways. I’m having a hard time seeing where there’s much to be lost here.

You already have an encouraging sign in that you two are still talking. So your real question should be where to invite him: dinner, movie, club again, etc. If you’re aiming to be cautious because this person is still a relative stranger, that’s understandable, so you just follow the normal policies: meet in a public place with others around, don’t bring him home until you feel comfortable enough, etc.

It looks like you’ve done well so far, doing the right things. The risk here is definitely worth it, so give it a go and see what happens!

--Friendly overture

To review: you’ve been there for her for awhile now, and as she’s going through what has to be a difficult transition (two kids and all) you’ve been there. And you also hit on the possibility of a rebound, which is definitely something to be aware of.

So, the risk: loss of friendship. The potential reward: a relationship with someone who, after three years, could pay off well, seeing how well you already know each other. She may have realized that she was missing something, and thinks you could fix that. Or she sees how you’re there for her, and just wants more of it – that’s a strong rebound sign right there.

I’d tread lightly as you’re doing, while she slowly disconnects from the previous relationship, and see what develops as she moves into steadier waters.

--Distant friend

If you want to be honest with her, you should tell her. There’s the risk that she may get scared off and disappear into the 1500 mile horizon, but even if she’s not interested she may shrug it off, say she’s not interested, and let it be done.

Many friendships have survived despite the unrequited feelings aspect and continued on without any difficulty; others have fallen apart. If you want to tell her, you’ll have to accept the risk of how she may react. Considering the distance, it’s unlikely it will have a large impact at this point, as the odds of being able to act on this right now are slim.

Good luck, and thanks for asking.

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