Does he like me enough to date me?

I met my best friend 9 months ago in our college math course.I immediately was attracted to his personality and looks but figured he was way out of my league. So, I figured I shouldn’t even give it a chance. Over the semester we’ve spent a lot of time together and message each other everyday with funny pictures and videos. He also makes comments like “you look really really good”, “I vibe with what you’re looking for in a relationship”, and when watching me sing and dance “I can’t look away it’s just so amazing.” He also moves from telling me about girls he met on tinder to not speaking about a girl in front of me. He even grabbed my ass when were tipsy one time. I get these crazy feelings when we’re together but I’m so afraid to tell him how I feel. It’s the classic case of not wanting to lose him. Do you think I should just tell him and risk the weird feelings if he doesn’t feel the same?

Well, he likes you, but is he hanging around with any other girls? Is he dating? I know what it's like to be friendzoned and you're right, trying to make a move on him can ruin the friendship. But you don't start out by telling him what your feelings are. You go out on dates. Invite him to go to places and do things. Get him in a romantic mood. Cuddle and snuggle and that sort of thing. Don't just jump on him. See if he falls in love with you over the next few months.

It sounds like he likes you but also wants to date around and be flirty. What is it you would like to see happen with him?

He also moves from telling me about girls he met on tinder to not speaking about a girl in front of me. He even grabbed my ass when were tipsy one time.

I’d like for him to confirm that he has the same feelings as I do. So then we could confirm we both like each other as more than best friends. Then move on slowly from there

As for whether he’s dating other girls I have no idea. When we first met we’d both talk about people we were seeing. Now neither of us talk to other about that. He also got pretty jealous once when I told him about this guy I as going to go on a date with.

I wouldn't label anyone a "best friend," especially after only knowing him 9 months, since most friendships change, evolve, fade away or even end, especially when it comes to opposite sex friendships. The thing is, the relationship you have with him right now will most likely ease onto the back burner when one of you gets into a longterm relationship. For one thing, if he gets a new gf, she won't appreciate how much you two communicate and get together because opposite sex close friendships have a different dynamic that sometimes doesn't sit well with a person's new partner. And don't think you can fool the new lady. She'll know you have a crush on her man. The same would happen if you get a new bf.

Knowing your friendship has an expiration date, I'd go for the risk of having a talk with him. He's not shy, since he compliments you and easily dates others. There could be two reasons he hasn't asked you out. 1. You two were with others when you met and he hasn't been clued in that you have a crush on him since you've both been single. Or: 2. He's just not that into you to ask you out, but knows you have a crush on him and it's an ego boost for him, and he's only jealous about you dating another guy because he's selfish and wants all your attention, even though he wants to keep it in the friend zone.

I'd probably say: We get along so well. What do you think about us giving dating a go? I once worked with a woman who the exact same thing happened to, and they married and had a son together. If you don't want to be that bold, step up your compliments of him and touch his arm for emphasis when you laugh and touch his hair and tell him he looks so cute today. The one thing you have to do is bolster your own self esteem. When you say someone is out of your league, it's a turn off when you feel so poorly about yourself. If you can't feel confident that you're worthy of someone, and feel like you're the treasure and they need to treat you special, don't enter into the relationship, because it won't turn out well. Good luck and let us know how it goes.

I wouldn't approach this with some awkward confession about your feelings....because...well...it makes things very very awkward.

Instead maybe keep it light and just ask him what he thinks about you and him going on a date or has he ever thought about you two being more than friends. Kind of open a conversation and see what he says. This way it's just a conversation about what if and if he gives you an answer you don't want to hear, at least you'll know how he feels and you can back away without all the awkwardness of confession and rejection.