I'm going on twenty and he's thirty. He's single, never married, not a complete bum, and not gay. He's one of my ten managers, and is the last hired, therefore, he's at the bottom as far as rank. I've known him for a year, we have become close. However, he's sociable and flirty, hence my dilmma. I am interested in him, but am not sure if he feels the same; and if he does, should we consider becoming romantically involved since technically he is my boss (I need a new job anyway, perfect excuse to quit right ;) ).
Here are some of the signs that confuse me as to whether he is interested in me, or just being friendly:
1. He smiles at me all the time. Whether it be from across the room or from two inches away, and when I look up and catch his eye he smiles. He's always in my vicinity; and he always seems to be listening, even when I don't think he is, or when I am not talking to him directly (which is awkward when he asks a question or recalls a minor detail from a conversation we had two months ago).
2. He commented recently that I look sad (I have some personal issues right now). He then preceded to make me smile and give me advice. He seems to genuinely care and want me to be happy even commenting that, if I'm miserable when he sees, me then I'm miserable when he doesn't and that's not good.
3. He talks about me to other people. He often calls me "the best", or when I help him with a project I somehow "saved his life". He's even gone to the extent of mocking fellow employees and saying that I could do something better than they could (which is a bit rude when you think about it and also a bit embarrassing).
4. He talks to me about everything! We talk about his past, family, future goals, and he always wants my opinion. We had a long conversation the other day about how he was starting to grow white hair, and how he felt old and stressed out about it. XD

So, from the little info that I have given, do you suspect that he is just being a good friend, or does he want something more? I'm just not sure whether I want him to be interested because I like him, or if he honestly is interested. Whether his intentions are romantically inclined or not, I value him as a person and a friend.

PS~ This is my first question, so thank you for taking the time to read it.

Find some function that you would like to go to and buy an extra ticket (of course side by side) then before the event tell him that a girlfriend can't make it to the event and that you are going to have an extra ticket and ask if he would want it. If he takes it and goes that would put the two of you side by side at a function that had nothing to do with work.

I have a feeling if there were any interest in you you would know it by the end of the function that you go to.

Jeez, all signs point to "he likes you" But maybe that's just me. Defintely find some sort of common interest, and when you find it, bring it up. Like "Have you heard of this new movie? It seems really good?" It gives him a chance to take the bait and say "well, maybe we should go sometime" you know what I mean?

Wow all of that points to the fact that he must like you! That is an overload of interest! The idea of ohsohappy is good I think.. :) good luck