Originally Posted by
TheEvilJester
Honestly... I'm sensing a theme here. You two hit it off... you two do something that at least hints that the feelings on both sides are romantic and not just friendly.... and then you two completely avoid talking about it. I don't mean to make it sound like I am over simplifying things.... but I think your path forward is pretty obvious. Talk to him about all this. It would be nice if things were natural and clear. If he asked you out, making clear it was a date, and things progressed as you'd expect.
But, it sounds like that hasn't happened. Things have remained ambiguous. Any time one or the other of you made any kind of move it wasn't clear if it was just a friends or meant something more.
Do you want to date him if he's interested? Or do you only like him as a friend? Think of that before you even bother to proceed, because how you feel on that will inform how you handle it if/when you proceed. But, either way you should talk to him. Make your intentions clear and ask if he is on the same page. If you two keep dancing around it, how do you ever expect anything to become clear? Believe me, I understand it can be hard to bring yourself to have that conversation... but if he's not making things any clearer, how will you ever know unless you ask?
Good luck.