I guess the best advice I could give you.. at your age, start as you mean to continue.
Most women, at least the ones that are worth having anyway, know what they want by that age, and aren't shy about saying something. If they haven't got it figured out by now they never will.
If you're not a moonlight, candles and roses kinda guy, why give them the impression you are? If a diner date (yeah, that's diner, not dinner) is your style, then go for it. At least you're being straight with her, this is what she can expect in the future.
Now, I will suggest a diner where neither of you live next door.. nothing worse than friends dropping in and chatting with you (or her!) while you're trying to get to know each other. And if it doesn't go well, having your buddies see you wearing a plate of spaghetti like a hat is a hard thing to live down..
Sean