Of course, there are worse outcomes to dating while time traveling. You could be like Fry on Futurama and become your own grandfather. I think that was how it went, at least (I assume the Internet will quickly correct me in the comments below if wrong).
Still, as a way of thinking positively, I like the time travel outlook.
BILLY: Pretend you've already asked her out and she said no.
BILLY: That way you're not expecting a yes, but if she does happen to agree you can be excited that you've just participated in changing the past through time travel!
TREY: She said yes. But I got so excited, I kind of spazzed out until she corrected the space-time continuum.
BILLY: *GASP* You mean she was the time traveller?