What can I do to make a guy friend more comfortable around me?

We have known each other for more than twenty years, since we were in elementary school. He was even my middle school boyfriend. But we do not live in the same area anymore. Our families are close and he seems comfortable around everyone else but me. Sometimes he doesn't even look me in the eyes. I the type of person who likes to get to the bottom of things. Should I confront him?


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What Guys Said 2

  • There are many potential explanations for his behavior, but I think two are the most likely:

    1) He's always had a thing for you, and whether or not you two could ever possibly actually be together, the fact that he's got you on this pedestal makes him feel shy and awkward around you.

    2) He knows something very personal about you. Does he talk to any of your exes or anything like that? If he knew some secret about you, especially if it's sexual in nature, or has seen pics or anything at all like that that could make him behave oddly.

    Of course, he could just be shy, I'm pretty shy, but never around my family and family friends that aren't my age. It could just be that he thinks you're pretty and is intimidated by that.

    My best advice is just to talk to him in a very casual way, talk about something he's really into so he can get lost in his interest in it. If he gets more comfortable as the conversation progresses, just say you're curious about why he was so shy before. Maybe even comment on how relaxed he is, and ask why he's not always like that with you. Something like that might get him to open up about whatever it is.

  • Talk with him, but don't "confront" him. Casually chat with him. Ask him questions about where he's living now, where he's working, just regular chit-chat.


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