We've gone out once or twice outside of work - each time we'd end up spending the better part of the day/night together. It's been fun and our conversations are a good blend of getting to know you and other deeper, more personal topics. He always pays but he hasn't made any move beyond that which might signal it's a date.
I think he knows I'm interested in him and he seems reasonably enthusiastic about spending time together. I'm just trying to figure out whether it's as friends or as something more.
Most Helpful Guy
You can't really tell. Just have to ask or spend more time together.
If he hasn't asked you out after spending some time together why not ask him?
He may just not find you attractive, he may just not want a relationship, he may be too shy. But I think most impressively from a man's point of view would be to take the initiative and call him on it.
Most Helpful Girl
He could be in a relationship. Or not sure how he feels about you