this reminds me EXACTLY of situation at work...boss is a 50 something whos daughter is off at college and comes to visit every so often. My boss is awesome though, hegoes out to the bars and strip clubs with us, jokes about his daughter going out with the nerdy guys at work (including myself

).
So first time i met her she was here for like a month living with him, well he goes off on a business trip for a couple days and that week we went out to lunch, nothing major, just cause she had nothing to do while he was away really. Second time she comes down we suggest she goes out to the bars, well her dad tags along so it was kinda funny. End of the ngiht though she says next time she is here we are going out without him

lol
So i say if the boss is cool guy and he likes you it wouldnt hurt to ask him. Dont try and do it behind his back thouh.