A fling from college that I recently saw out. Do I initiate that I'm interested?

5 years ago when I attended college, there was a guy in one of my lectures and we almost had this immediate attraction but barely ever spoke to each other. We once did briefly text but I don't remember how we got each other's numbers. We would see each other around college but were too afraid to say anything to each other. I ran into him a while after in a bar and we ended up having a one night stand, nothing happened after that but I would occasionally see him look at my Instagram stories. Fast forwarding possibly a year later after the one night stand, I saw him out with a girl who was his girlfriend (we just sort of looked at each other and that was it), within a week or so I noticed he became single via social media.

Do I like one of his photos/indicate that I'm interested or leave the situation alone?

Up to you, but I wouldn't be dating someone who was only about a week out of a relationship. Regardless of who they were.

At some level you realize that he is not interested and has never contacted you directly. Unfortunately you wish to interpret social media postings, glances etc as a secret wish to have a relationship. It's time to stop obsessing over him and get on dating apps if you are seeking a relationship.

Think about it logically, though. If he wanted to date you he has your contact info and would simply ask you out, right?

5 years ago

I ran into him a while after in a bar and we ended up having a one night stand,

I noticed he became single via social media.

At some level you realize that he is not interested and has never contacted you directly. Unfortunately you wish to interpret social media postings, glances etc as a secret wish to have a relationship. It's time to stop obsessing over him and get on dating apps if you are seeking a relationship.

 

Think about it logically, though. If he wanted to date you he has your contact info and would simply ask you out, right?

Valid, however, we've both changed numbers since then.

Has he contacted you for a date yet?

Valid, however, we've both changed numbers since then.

You can contact him again, but all that will be on his mind is another one night stand. My perspective, if he was interested in more than a fling he would have initiated it.

You've got nothing to lose and he's just a guy out of many guys. I wouldn't overthink it and just message him. Greater mistakes have been made, larger long shots have been fired, greater problems are out there. You're in your twenties (?). Have fun, get out there, meet people and don't be afraid to take chances.

What happened to Mr Wonderful from the thread a few days ago? Why are you prowling bars looking for old flames to pick up?🤔

I'm (24F) seeing a wonderful guy (29M) who I admittedly share quite a lot of interests with.