I’ve been pretty much best friends with a guy for about five years. The whole time there has been underlying romantic tension; we are both sort of shy (not with each other but in any uncomfortable situations), and neither of us has really made a move at any point.
Valentine’s day last year (2015), he admitted to having some feelings for me, and me, being really horribly awkward, just sort of replied like, “aw thank you”, because I also had complicated feelings for someone else at that point and wasn’t sure if I wanted to start something. Now I do want to start something, but I am a big baby about talking about feelings.
We flirt pretty much constantly, but I don’t know if he realizes because that is just how we have always talked, and he isn’t very good at taking hints. I don’t want to be the person to make the first move, but I feel like I have to, and soon, because he just graduated high school (I will be a senior next year). While he is staying in town, his dorm will be about 45 minutes away rather than 5 minutes where his house is, so I feel like starting something would be easier now.
I know everyone will probably just say to go ahead and ask him, but I am just the tiniest bit nervous that he doesn’t actually want to date and just wants to keep up what we have. It is okay if you are just going to tell me to talk to him, I would like some reassurance and motivation anyway. Thank you!