We'd been friends since first year of college but never that close, now as seniors he has become one of my closest friends. We chill for hours and hours, having interesting conversations or just being silly and random. I'd not been feeling romantically towards him until 2 weeks ago we spent a Friday hanging out and went to a party and walked around and I suddenly kept thinking of kissing him.
The next day I was thinking so much about him and that night he messaged me and we had the most vulnerable philosophical personal conversation I'd had with him or seen him had with anyone. He came over at 2 AM and we continued it in person til 6 AM when he fell asleep with us cuddling, which we had never done before (I'm the one who sparked the cuddling but he swirled his fingers around on me and stuff). Some moments it felt like maybe we'd kiss but I sort of kept just enough distance because I wasn't sure. Through the night and in the morning there was no more cuddling.
Since then we've hungout and talked more than ever, often with him initiating, and usually just the two of us. He makes me feel so good about who I am and verbalizes how special it is that we can hangout for hours and personality qualities about me that he thinks are cool. Sometimes it seems like there is definitely flirtatious eye contact but other times it feels totally friendly.
There is a girl he has been friends with benefits with for years who he references a lot, but always refers to as a friend and doesn't mention the benefits part. She is a freshman at another school and he's on his way to visit her for the long weekend. As I was driving him to the airport, he said he was excited, but didn't say it that enthusiastically, and didn't mention anything about her. Again, at some points I felt flirtatious eye contact, and he seemed excited to hangout when he gets back Tuesday.
What do you make of this situation, and how he might feel?
What should I do or not do for the sake of our friendship, etc?
get over it, stay friends
stay friends, wait to see how he feels
just try to kiss him or be clearly flirty
have a conversation (lots of options... have you ever thought of me in a different from a friend sort of way? was i off base in feeling like we were about to kiss that night? how are you feeling about elyssa lately? i've found myself thinking about you a lot lately... or a plethora of other approaches i could take to have a convo)
Most Helpful Guy
I believe in doing nothing to jeopardize the friendship. The friendship you describe comes along so rarely, if at all, in life that it is in no way worth losing for any reason. My closest friend is a woman I've know for 18 years. I would never want to take a risk that might have a chance of messing that up. There are plenty of other women to have relationships with. If you are inclined to take the risk, you are saying you are willing to face the consequences of that decision. If you lose, you can't complain because you did so knowing it may happen. I hope you use common sense and logic in your decision. He sounds like a truly wonderful man that rarely comes along.1