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How do I show a friend that I'm interested, without risking the friendship?

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Question - (25 February 2006) 2 Answers - (Newest, 26 February 2006)
A female Iceland, *hoenixstar writes:

Hi, I have something that I’d like to get advice about. I’m really attracted to a friend of another friend of mine, who began hanging with my group of friends a few months ago. I’d love to let him know that I’m interested in him, but I’m shy about that kind of thing, and scared of rejection, so I’m not sure how to go about it ... Also, although we have very similar interests, and get along really well, I’m worried that becoming good friends with him first would just make me even more scared of making the first move, as I’d be frightened of losing him as a friend – this has happened before. What should I do?

If anyone has advice for this situation, it would be greatly appreciated!

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A reader, anonymous, writes (26 February 2006):

This is one of those oh-so-rare instances where I recommend subterfuge, so congratulations.

You say he hangs out with your circle of friends? Take aside your closest and most trustworthy one from among them, swear him/her to secrecy, then dispatch them for a little investigative work. Get that person to ask whether this new face is interested in you (or would be), and act accordingly based on his response. If yes, go for it, if not, nothing lost.

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A female reader, anonymous, writes (26 February 2006):

If you have similar interests, try to set it up so the two of you end up doing something on your own. Ask him if he wants to go see some museum exhibit with you, or invite him to something you're doing so that you have to go over to it together. The trick is to get some time alone with this guy. Then see how much you have to talk about.

If he's interested, you'll find that you just naturally end up spending more and more time together, because he'll be doing the same thing, or at least hoping that's what you're doing. Meanwhile, in case he's not interested, you've still got plausible deniability - he won't be forced to interpret your invitations as a full-on come-on, so the friendship won't be threatened with weirdness, as long as you're attentive to his responses and don't pursue too much.

As for not wanting to make the first move on someone you've become close to for fear of losing the friendship, that only makes sense if you'd rather have this guy as a friend than something more. if you're interested in dating him, it shouldn't matter whether you officially start dating him and then get to know him well enough to see whether you really care about him, or get to know him well enough that you really care about him and then officially start dating him. Except that in the latter scenario, you're more likely to actually get to know him, since you won't be bothered with trying to take each other's clothes off, initially.

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