How do you turn friendship into something more?

I met a really nice guy last weekend at my brother's wedding. The hard part is trying to figure out whether it's one-sided. Since he is such a nice guy and is friendly with everyone he meets, I can't make a big deal out of how he treated me. He lives far away, and the chances of seeing him again are few, but I can't get over how good he made me feel. Any suggestions? I would like to make attempt at this, but I don't know how. I think that my fear of making a fool of myself (and rejection) may hold me back.

There are two challenges here: first, the question of how to approach him without embarrassment and losing the friendship; second, the fact that he lives miles away. Let's deal with the second one first, because it's something you should think about before doing anything.

If he lives far away, what are the chances of anything coming of it, even if the feeling is mutual? Are you prepared to move to where he lives, if you do start something and it's looking good over time? Is there a chance he might move closer to you? The reason I ask is that long-distance relationships can work, but only if there's some light at the end of the tunnel -- in other words, if you both know eventually you will end up living in the same place. Otherwise, what's the point? So if you have no intentions of ever moving, I'd think twice. Maybe approach him as a friend and check out how stuck he is on where he lives before suggesting anything more.

If after all that you're still convinced you want to give it a go, here's what I'd do. Start by sending him an email (if you don't know his address, your brother will). Email's a nice place to start. It's less embarrassing than a phone call, you don't have to think on your feet, and you can get a trusted friend to read it before you send it to make sure you've struck the right tone. I'd send a cheery, it-was-so-nice-to-see-you type of email, simply thanking him for making a nice day even more special. If the reply is nice and it's obvious he enjoyed your company too, send one back pretty quickly. Again, keep it chatty and ask how life's treating him, what he's been up to, that sort of thing. If you don't know if he's got a girlfriend or not, it's pretty easy at this point to add a ''How's your love life?'' jokey question. Again, he'll reply (and you'll get a feeling of whether he's keen by how quickly), and before you know it, you'll have a nice little email relationship going. How then to move it from friendship onto finding out if he's keen on you? Start adding affectionate little things like ''Miss you,'' or ''Wish we could continue this over a drink'' or ''Any chance of you coming back here for the holidays? There's a great restaurant here you'd love.'' Again, watch his reaction. If he's not keen, he'll hint at a girlfriend or reply in a way that makes it clear he's just a friend (''I'd love to but I'm having way too much fun here at the moment'').

By now, you should have a feel of how he feels, and if he still hasn't taken the hint already, there's nothing for it but to take a deep breath and put yourself on the line a little. Try saying, ''I had a dream the other night that you and I were together. Weird, eh?'' He'll reply in one of three ways:

  1. ''Totally weird! Whatever made you dream that?'' (Forget it. It's just friendship.)
  2. ''What did we do?'' (Any general curiosity probably means he hasn't thought of you that way before but is fast warming to the idea).
  3. ''Why weird? Now you mention it ...'' (The desired response -- and the rest will be history).

Good luck!

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