Should I tell him how I feel?

[Moomoomilk]

Hi guys. Thanks for reading this first of all. All comments are appreciated.

I have this friend. We are long distance but have been friends for a year and have hung out in person twice. Since I met him, I've had a slight crush. But when we met he mentioned how he didn't want a relationship and blah blah. He's also mentioned since how he wouldn't want long distance. So I think, okay, we're friends. It goes like this for about six months until he mentions possibly being friends with benefits. I agreed to this because I thought it would be fun and was what I wanted too.

Well, long story short, this last weekend, he and I were finally able to spend three days together, mostly alone. We had a hotel room and shared a bed. Before the weekend, I made a joke about having sex that weekend. He told me then that he was actually nervous and he didn't know if anything would actually happen.

I had kind of thought before that maybe, maaaaybe, he may have wanted even more than just fwb, but wasn't sure what I wanted and was afraid to ask. He's a shy introvert with anxiety, much like myself. Haha.

But anyway, nothing ended up happening even though we spent three nights together. I had a great time though, and so did he.

But now, I have even more of the feeling that he is actually into me. But I'm worried about being wrong.

And the way I feel is, if he wanted more, I'd be into it, but if he didn't, I'd also be okay with that. So now that I really feel like he likes me, I'm thinking about what would happen if I told him I'd be up for more because I like him too.

Just some examples of why I get the feeling he's actually interested in me are..

He seemed interested in my dating life. He asked me about people I'd mentioned to him that I was talking to/dating a couple times over the weekend. One of them was from way back in October and I didn't even remember who he meant at first.

He didn't ever really want to look me in the eye, especially when we were just laying in bed, or looked away when I looked at him and he had been looking at me. He was also super nervous at first, like basically all of Friday he was a bit awkward.

Through our whole friendship, he has mentioned us living together at least five times. The first time was when he brought up possible fwb. And then a few others. And over the weekend, he mentioned at one point how he would never move for someone unless he was in a long relationship with them, but yet he and I have discussed him possibly moving in with me where I end up a few times. And then later in the weekend after saying that, he says, "well, you should just move up here!". Another time in the past too he has mentioned something along the lines of "well, you just move here and we'll live together and work and figure our issues out together" or something like that. He mentioned again how he wouldn't do long distance once over the weekend too.. So maybe that could be why he won't say his feelings if he has them? Idk

He kept saying as well how he wanted me to visit again. We already have plans for me to visit again in October. But when I was leaving after the weekend too he said something like, "you should come up for blah, or just whenever! I'm free pretty often". And when I told him I got back home, he told me he'd been sad since I left. Which yeah is normal for just friends too, but yeah.

General flirty things happened too, on both sides. There were several times where i could feel the chemistry we had flowing, and like we should kiss or something, but obviously that didn't happen.

He also made a comment about how he wanted to be friends for the rest of our lives at one point over the weekend.

He's told me before I'm one of his best friends. We talk almost everyday and he tells me his feelings and everything like that. And a lot of personal stuff. I do the same to him.

Basically when I left on Monday, I was really confident in how I felt. Like, basically how you'd feel after a first or second date that went really well. I was all, hell yeah! I'm gonna just tell him I like him. I bet he likes me too!

But clearly, I've had time to think since then and am just unsure. All my friends think I should ask him about it, but I'm worried about ruining our friendship or making things awkward.

One extra thing that happened that I wasn't sure what to make of it was, we were talking and he was telling me about a friend who hooked up with another friend. The other friend had a history of sleeping around and I said "yeah, that's definitely not the guy to fall for" and he said "I wonder if that's me, not the guy to fall for" and I said "well, you make it seem that way" he said "good haphaha" so I said "lol, I thought you wanted to be with someone eventually?" He said "I do, but I was just embracing it haha". I wasn't quite sure how to read that either if it meant anything.

I don't know, there was even more I wanted to say but this is long enough already. Basically, my intuition from the experience is telling me he's actually crushing on me, but he afraid to say something because if I'm not feeling it it might mess up the relationship. Which is basically also what I feel. I'm probably over thinking it, and I just need a third party opinion before I decide to bring it up to him. What do you guys think? I'm sure I have more to say as well if anyone has a question.

Should I tell him how I'm feeling? Or should we stay just friends and keep going how it is?

Edit:

Reasons I'm worried about telling him are, possibly making the friendship awkward. If he doesn't like me, he could be weirded out and not want to be as close any more. He also told me in the past that his past two friends with benefits have ended up wanting more but he didn't. But I also know that they weren't as close to him as I am, and that he didn't feel any chemistry with them, and I really feel there was no way he didn't feel it when I felt it this past weekend...

[musicman777]

Reasons I'm worried about telling him are, possibly making the friendship awkward. If he doesn't like me, he could be weirded out and not want to be as close any more. He also told me in the past that his past two friends with benefits have ended up wanting more but he didn't. But I also know that they weren't as close to him as I am, and that he didn't feel any chemistry with them, and I really feel there was no way he didn't feel it when I felt it this past weekend...

 

It sounds to me like this friendship already is "awkward". I've never heard of two people that agreed to set up a three-day getaway in hotel to have sex end up not doing anything, this whole thing sounds a bit odd. This guy certainly does. It's hard to understand his angle with you from how you describe him. It sounds like he is playing an awful lot of games.

 

I don't know... if you really think you have feelings for this guy, there is no point in keeping them bottled up. It will only make this friendship more difficult to maintain over time. You should just tell him how you feel and what you want and see how he responds. If he doesn't want a relationship, move on with your life. Because you are just going to waste your time. I personally don't see this relationship going anywhere if he does want one, but I could be wrong. He doesn't sound like a real winner to me.

[Wiseman2]

Why not visit each other at home? Is he married/living with someone? It sounds like he just wants to be friends or roommates.

Well, long story short, this last weekend, he and I were finally able to spend three days together, mostly alone. We had a hotel room and shared a bed.

[Moomoomilk]

He lives five hours away from me, sadly. He currently lives with roommates. When I picked him up he showed me around the house. And on the last day, I gave him a ride to work before I left for home and we hung out at his house for about an hour before that and ate breakfast and what not.

[Moomoomilk]

It sounds to me like this friendship already is "awkward". I've never heard of two people that agreed to set up a three-day getaway in hotel to have sex end up not doing anything, this whole thing sounds a bit odd. This guy certainly does. It's hard to understand his angle with you from how you describe him. It sounds like he is playing an awful lot of games.

 

I don't know... if you really think you have feelings for this guy, there is no point in keeping them bottled up. It will only make this friendship more difficult to maintain over time. You should just tell him how you feel and what you want and see how he responds. If he doesn't want a relationship, move on with your life. Because you are just going to waste your time. I personally don't see this relationship going anywhere if he does want one, but I could be wrong. He doesn't sound like a real winner to me.

 

Thanks. I think I should just tell him too. I probably make it sound more awkward than it is, lol. I know I don't really have anything to lose. I don't think he'd let it mess with our friendship if I told him. Because I know I'd be able to move on if he didn't feel the same way. Not knowing for sure is killing me, so I'm going to tell him. I just have to work up the courage and find the right time. Lol

I should have been more clear too. The weekend was an opportunity for us to spend time together. It was his friends wedding and he invited me to be his plus one, and then we just stayed a couple extra days for time to hang out.

[Wiseman2]

Sounds like a lot of work for someone with such ambiguous intentions, no?

He lives five hours away from me, sadly. He currently lives with roommates. When I picked him up he showed me around the house. And on the last day, I gave him a ride to work before I left for home and we hung out at his house for about an hour before that and ate breakfast and what not.

[Moomoomilk]

Sounds like a lot of work for someone with such ambiguous intentions, no?

 

I don't think so, because we have been good friends for a year like I said. Hanging out in person is important to both of us. I didn't go there specifically because I thought he liked me. I got that feeling waaaay more after spending the time with him and seeing how he acted and the things he said. I went there for the opportunity to hang out with my friend for a few days and have a little mini vacation type of thing.