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!
LemonVibe 
hey!! looks like we’re both in similar situations. i also liked one of my best friends, except i had only known him for 2 years, but he basically acted like my brother. I know making the first move is hard, but it’s a bit easier for you because from what i’ve read, it seems to me that he still likes you. People always say, tell them in person, it’s better that way, but no its not. If you have no problem with telling him in person, then go ahead. But you should tell him in a way that you’re most comfortable with. From my experience, I told that guy over text and he said almost the same thing. “ahaa thanks” and that was that. I got rejected of course because i knew he liked someone. As for timing, if he’s not ready to date, you could tell him that its alright and it can wait. that’s would i would do, but i’m a freshman going into my sophmore year soooo idk much about relationships yet, cause i’ve never been in one. But all i have to say is good luck. 🙂