Are these signs a guy is flirting? interested romantically?

I am confused by this person's actions and words. I work as an intern at a university and the head professor of the department who trained me for a couple of months has been acting strange. He does favors for me like give me supplies for my office, shares his coffee and muffins with me in the mornings, and has started to discuss things beyond professional topics. For instance, he brings up relationships, tells me how dating is not easy etc. He also told me 'you are smart, sweet, gorgeous, and you are a hottie. Every guy would dream of you." He gives me compliments on how I look and I catch him checking me out. During our convo about dating troubles and him telling me "you are stunning" he told me about some woman he has been dating on and off for two months and that it is not going well, he is not too happy and that there are problems. Does he like me or something? Then why would he tell me about this woman? He seems to want to talk about personal stuff and shares things with me that he won't with others. I have invited him to come by to my desk and we chat-he tells me personal confidential things regarding his life and job that only his own boss may know, saying that he trusts me. My guy friend says that when a guy does is it's because he likes you.
The weird thing is that when we are with another person he kind of avoids showing me attention-is this to avoid anyone picking up on something? People stare sometimes when we are talking in the hallway and he will say something like, "I will send you the reports soon and you type it up for me." Yes, the convo started about reports but ended up lasting about 30+ minutes and is about personal lives ect.
Last week, he even cleaned dog poop off my tires and when he does things he's like, "see how I take care of you? all the things I do for you?"

I started there several months ago. I am 22 and he is like 34-35. He seems nice and is good looking. I like him , but why would he tell me about the woman?
I want to push him in the direction to ask me out, but how????

This morning, he was telling me about someone who prank calls his house and we got into this convo about prank calling. Then he said, "Give me your number so I can prank call you."
Now, was this as a joke, or kind of hinting that he really wants my number?

I just need to feel secure that he is interested, but want to make him move in the direction to ask me out.
Do these signs sound just friendly or like something more? ( I esp. thought the coffee part was cute).




NOW, HERE ARE MY ACTIONS:

Last Thursday, I brought in bags of Kona Coffee and he wanted a cup in the break room. I made some for a few people. Then he told me on the phone that he liked it very much and I gave him two bags of it with a cute note saying, "Here is some more of that coffee you liked. I even gave you my favorite flavor." He then went when he spoke to me later on that day that I write him the best, nicest, messages.

An hour later:

he walked around the dept, past all the offices, but stopped by into mine to say, 'good morning." Only mine, nobody else's. Then this afternoon, on the phone he told me that he was drinking my coffee and that is was yummy.


I am feeling a bit more sure that he is interested romantically and it gives me a bit more guts to make the move and ask him out for coffee.

Do these signs sound just friendly or like something more? ( I esp. thought the coffee part was cute).



I am told that I am an attractive and smart girl, but I am feeling nervous and insecure. I don't want to risk me imagining that he likes me. This is why I need some male advice on whether he does like me, and ALSO, how else should I flirt without seeming easy?? More coffee?