How to break it to a guy that you're interested? Asking the guys (advice from girls too) HELP!

I can’t stand this! Okay, while I invite girls opinions, I really need the guys to weigh in on this one. It should be fairly cut and dry, I hope, and I’d really appreciate your help. I also apologize ahead of time for length.

I like a friend of mine (the term friend is used loosely, we aren’t very close but more than acquaintances), and I’m fairly certain he is interested in me, to a degree. The thing is, we’ve only ever hung out a few times in person, but have chatted a lot online, mostly via myspace (yes laugh, I make fun of it too and slightly judge myself). However, that was because I spent the first three months after we met on the opposite side of the country (I go to school on one side, was on summer break on the other)., and because he works a lot so finding time isn’t always easy.

Over that first break, I started dating someone. When I got back into town, me and the current the guy were talking about hanging out, but the one week he really had time my then boyfriend was coming into town, and then contact began to dwindle after I mentioned the bf.

We started talking more around x-mas break (after me the boyfriend broke up) and hung out once when I first got back. When we hung out, the comments he made certainly insinuated that he was interested (they were fairly obvious). I slightly panicked (not good at realizing my own feelings), and realized I liked this guy.

We haven’t hung out since that night, but have texted a few times (all very flirty) and messaged a bit. I definitely got a bit overeager/nervous and suffered a case of mild word vomit on the messages and we stopped talking a bit. Then it started up (he insinuated it). We recently chatted on aim, however I’m not sure how that went.

Now, I hate aim. It’s so impersonal. I like people and hearing their stories, and part of that involves non-verbal communication. You can learn so much about a person from their nuances, gestures, facial expressions etc. I’m not a fan of this social networking/online stuff. He however is. He is all about the internet and aim/facebook/myspace/blogging, etc. And that’s fine, except that the aim conversation was awkward to me. It wasn’t my comfort zone and was totally his. He was definitely in control the whole time.

We are at a standstill. I know that he is either interested in me in a vague sort of way, or actually wants to see where this could go, but I can’t tell. Also he has insinuated things but never blatantly stated anything. Part of me thinks that he might be a bit shy. I’m thinking about just finding a way to hang out and then, after the evening is winding down, confront him and say “Hey, I like you, and would like to see where this goes. So yeah, you ponder on that” Just to get it out there. I hate this back and forth. But I can’t seem to figure out how to get us to hang out.

So I ask, is that a good idea, if not what would be your suggestion, and if it is a good idea but I cannot get him alone in person, how else should I break it to him?


Most Helpful Guy

  • If you happen to both be on AIM before you see him in person again, let him know that you'd really like to ditch the electronics and see if there's a way the two of you can actually talk in person, then ask him to let you know when a good time is for you to get together. Don't let the conversation end until you both have a date and time set. If you were to say something like, "I like you," and just leave it at that, that opens up the door for more flirting, and possibly more word vomit.

    I learned this in church and in sales -- you will never get what you do not ask for. Instant messengers don't have to deter us from saying what we really want or really mean. Take this opportunity and let him know how you feel about him. He may very well be shy, but he backed away a bit when you were dating someone else, so that means this guy has some integrity, and you would probably do well in getting to know him a little more. Go for it, and let me know how it goes.

    • You know, I completely agree. After reading this I went ahead and pretty much gave him a time frame during which we need to do something in person or I'm done. I told him I shouldn't have to always badger him into doing something with me, which got him moving a bit. I'm waiting to hear back about his work schedule. So that's promising! Now let's see if we can rip the other band-aid off. Thanks for your advice. It was really sensible and I needed to hear it!

    • I really like the ditch the electronics thing. I think I'm going to use that too!

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