Strings Attached?

I have a research advisor here at school who often takes on the role of sugar daddy. Through a lot of good luck, he has found himself with more money than he knows what to do with, and for some reason, he is very attached to me. It may be the fact that he taught my mother when he was just starting at this college and liked her quite a lot, it may be that I look eerily simillar to his wife (who was a model for Yves St Laurent many many years ago, omg!) but I think it's mostly fueled by typical old-man desire to "help" people. I think he has reached the age where he wants to leave a legacy, and he has more or less been disappointed by his children.

He plays the role of doting father, but because I have never experienced that, I'm sort of uneasy. That doesn't stop me though, I've already let him buy me a very expensive Cole Haan purse, to slip me envelopes of cash when I go out of town for a weekend. My pride and my desire for true financial indpendence are sometimes outweighed by my materialism.

Starting in May, I'll get a graduate student stipend. My advisor will supplement this stipend, because he can. I know that he expects more of his graduate studets than most do. The extra money means working longer and harder, that's reasonable. On the DL, he's giving me a few grand to "invest", as long as I meet with him a few times a week to to let him advise me on my investment strategy. Ok then.

My boy is visiting this weekend, and he will meet this very weird man. Before meeting him, my advisor has offered his frequent flier miles to anywhere in the US, for Spring Break. Reaction #1- hells yeah! Reaction #2- You are a creepy creepy man.

I have experienced that, in accepting these sorts of favors, there are always strings attached, even if it's just a nagging feeling that you don't deserve what you have or that you'll always be indebted to someone. I can't decide whether to accept the tickets or not. S is uncomfortable too, understandably.

I told my advisor's other grad student about his offer. "Aww that'll be so much fun, that's so nice of him!" he said.
"Yeah I don't know, it's kind of uncomfortable."
"Nah, why's that?"
"Well, I'm not sure how my boy feels about it...."
"No?"
"Well, how would you feel if your girlfriend worked for this guy that liked her a lot and spent a lot of time with her, took her out to dinner a lot, bought her a lot of stuff, got her drunk, and gave her expensive gifts and vacations and was taking her to France this summer?"
"Oh no, that would not be ok, I'd wanna fight 'im."
"Yeah, you see, it sounds really bad."
"Shit yeah. So your boy's gonna meet him this weekend?"
"Yeah. Oh, it will be some fun."
"Is he gonna start some shit? Is he gonna try to throw down at dinner, he gonna get mad and shit?"
"What? Oh, no. No he's not like, retarded!"

We'll see. Either way, it will be interesting. And damn, I'd love a long weekend in a hotel room with my boy over break...