Men - does it seem like he's inti me or just trying to be my friend?

If you have ever dateda younger woman before (i.e I am 25 and the man I'm interested in and who I think likes me is 40), how did you let her know you were interestedin dating rather than just being nice? He was a teaching fellow of mine at my law school and now has been promoted at another university, and I work at a firm so we dont have that student-teacher conflict anymore (and havent for 1.5 years now!)

He asked a mutual friend of ours once to ask me if i had a boyfriend, and when I was looking for housing over the summer, he connected me with one of his female colleagues who needed a roommate. He's asked me about my plans for the future, where i want to live and do in my career, and we've been out for dinner and coffee twice. Would you do those things with a girl youre just platonic with? Does it sound like he likes me or just being nice?