Should I Try with him?

[livvy1123]

I hung out with this guy last night and we have been talking for the whole summer planning to hang out since June (he was away). When he got back he kept asking to hang out and we made plans. So we hung out and I kind of thought from how we were talking before that he wanted to hookup with me but he didn't try once. I feel like some of the conversation was good but we were both kind of awkward and silent. After he dropped me off I sent him a snapchat saying "lets hang again soon " and he said "ya for sure". And he had asked me if I was going to the football game so I decided to go but when I did he didn't say hi to me at all. And then I said "I left the game because it sucked" and he said he was "going out" but he didn't invite me and now he's at a party up the street from my house. I don't know if I should keep trying with him or not because I've been hurt by guys who didn't like me back in the past badly and I have really huge emotional walls so I don't know if I should subject myself to getting hurt again if I can't tell if he had a good time last night or if he actually likes me. I really like him but I don't want to seem desperate by asking to hang out again and by starting all the conversations but I also don't know how to show him I like him without looking stupid. HELP!!!!

[Jacob]

Hi Livvy!

Welcome to Scarleteen!

I am just going to start by asking what you would like from the situation with him? Would something casual be ok? Are you looking to date for a longer period of time to be more like long term partners?

For sure it can be worthwhile to be open minded to different options but it sounds like neither of you are expressing what you want but are being careful to come accross as casual. So between you it's totally possible that you aren't actually both interested in the same thing.

I will say it does sound unbalanced if you are initiating conversations and he is not.

I think there is nothing wrong with appearing interested and enthusiastic. If he doesn't feel the same way it's his responsibility to politely say no rather than your responsibility to not seem 'desparate'.

I totally don't like that word! I totally celebrate you finding someone attractive and wanting to express it.

It sounds like that self expression will do you both good. You could even ask him more directly what he would like to happen. Then you can hear what eachother want and decide if you agree!