Did I miss my chance?

I've been friends with a guy for over 5 years. We went to college together. During college we'd work a few projects together, sometimes they'd go well into the night because of the limited hours already in the day. I was really tired one time and laid down on his bed, after ten minutes he wanted to relax too (haha..right). So he laid down with me, caressed my arm, commented on my soft skin.. and I told him I had to go. I was chickensh*t, I admit it.

After college we met up a few times (I had moved away, but we stayed in contact). During one of these visits, 2 years ago, I was flirting with another guy - seeing what was there. When he saw this he flat out told my friend that that's what he is trying to do. So she pulled me away from the other guy. She told me later, but when I was taken aback that he liked me that way, I said we're friends though (I was boggled that he could still like me that way). Within the hour, she was with him. I was wishing the rest of the night that I had reacted differently.

Then earlier this year, I came out to visit again. Of course we made it a point to see each other. It'd been the longest time apart (over a year) that I've seen him. I now wear glasses when I'm too tired to deal with contacts, he'd never seen me in glasses. For the first half of the meal he hardly looked at me. I finally found a topic that made him react like his old self, the second half of the meal went better. I left, and felt awkward from that meal. So I texted him, what happened? Did my glasses throw you off? Were you mad at me? Why was it so wierd. He wrote back that he was nervous. I made a joke, and we ended on good terms - he actually texted me that there was Never any way he could be mad at me.

Now, I have moved back. Shortly after that earlier visit this year he started dating an ex. A few weeks after I moved he broke up with her. I've tried subtly flirting with him. However, now he seems like he wants to live a playboy lifestyle. He's lost the sensibility I saw in him for the first years I knew him. I did work with him this past weekend, but he was my "boss". So I tried to keep it professional. However, we did have some alone time. I gave him a compliment. He would caress my back. At one point he was touching my shoulder and gave me a mini massage, so I joked and told him to do the other side too. We were around co-workers.

His life is pretty busy now. I figure he's already tried to ask me out a few times. I just wasn't ever ready or initially in shock that he was interested. If he wants to he'd call right? Or is he now probably just comfortable with me. It's not like he goes for my hand when he touches me. Small of my back, shoulders, arm.

I promised myself I would stop asking guys out (honestly, it's all I do to get dates). Two guys have asked me out, but that's after they found out that I liked them first. Should I bite the bullet on this one, since he's tried in the past already?

Updates:
Should I flat out ask him out? I know I wrote below that I'll take it slow. However, since I know in the past he liked me - should I just ask him out? Or not force it.
I did finally ask him out. We were at a mutual friends party. I wrote him a letter, because he really confused me that night with the way he was touchy freely. That mutual friend also made a comment how we can't take over his bedroom. which made us both give a huh reaction. In the end, he was actually back with his Ex. Different timing we may have given it a shot. We now know what each other feels. It's because of our friendship it didn't get weird. Now it's up to fate if we ever give it a shot

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Most Helpful Girl

  • I say you too need to go out on a DATE not a dinner get together. Don't wait for him say how you feel before it truly becomes too late. If you don't feel the same way he feels about you don't force anything. But at the same time don't watch him walk out the door alone. He obviously likes you and you know it, I think you like him too. Take a chance and call him and ask him don't wait for his call because truthfully he might be waiting for yours. It's like a book, you can't just stop in the middle and guess what happens at the end. Go for it and call him.

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What Guys Said 2

  • Call him-or email him and be completely upfront. Tell him this question is a bit embarrassing but the consequences of doing nothing maybe too great. Tell him you got the sense that his feelings had changed and that he was interested in you romantically. If you are wrong he will be flattered. If you are right you'll be happy you did. It's a bit risky since it may embarrass you but really, nothing to be embarrassed about. It's bold, impetuous and hot.

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  • Dude probably lost hope. You can't expect him to keep it up. I mean he might, but you can't expect it. If you want something to happen on this one, you gotta make it happen.

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    • Thanks. That's what I figured. I'm just gonna take it slow though. Try to feel him out. At least put us in a situation where it's not business and we can just talk.

    • Yes... Just flat out ask him... Don't worry about that going slow business.

What Girls Said 1

  • If it's meant to be, another chance will come...

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