Oh and I can’t stress this enough, if you’re not already dating, do NOT go with the roses idea or presents or other grand romantic gestures. It will look desperate, and girls hate that.
This is largely great advice, but I diagree with the “should” part. When guys did that with me it sounded smarmy at best, and always got a raised eyebrow and a “Oh we should huh?” from me. This is not the time for sales tactics.
Don’t be manipulative, just ask. And don’t be silly and just sit around thinking about it. Plenty of girls sit home on prom night wishing somebody had asked them. Often the prettiest girls, because none of the boys ahd the cohones to just ask them.
Which then gives me a chance to reply with a charming, witty and ever so slightly cocky response about how you definitely should. A lot of women, especially younger women, respond well to a bit of cockiness. I will warn the other guys out there that it is really easy to go overboard on this. You’re aiming for confident, self assured, and not afraid to show off your positive attributes, not boasting, jerkish buffoon.
First you have to get rid of that "One time I went to a fight and a hockey game broke out… " thing. It’s lame, and old as dirt.