Most Helpful Guy
Of course you should go for it. I mean, Valentine's Day isn't a particularly special day for me so I would have no trouble asking out a woman on Valentine's Day. Although, I know what would happen -- I'd show up at a restaurant and wonder why it was so busy. I'd try to get a table and they'd ask "Do you have a reservation?" followed by the bad news -- the place is booked. I'd end up having to take her to some sort of ethnic food, which isn't bad... just not what I had in mind.
Most Helpful Girl
I don't think that's a good idea, but do whatever you want.