I met my present wife through an online dating service. I've gotta say though, it was an adventure.. it was pretty easy to tell why a lot of the women were single.
I remember one had 4 kids, and was pining for more. I like kids, but more than 4.. really?
Another had her whole life planned out, her biggest challenge was how she was going to "fit" me in to it. Mm hmm..
I soon learned that unless they asked questions, the best thing I could do was just nod and listen, the crazy ones were soon smoked out. Some had that figured out too, the more I said the worse it got. Go figure.
One had a psycho-ex-boyfriend that actually had me worried. I liked her, but she wasn't worth the trouble up front.
And my personal favourite, (other than the one I married), was the really gorgeous 35 year old. We spent a lunch date together, and by the time it was done so was I. I remember telling her, "I think I see why you're still single, you're nothing short of a bitc*!"
I did meet some sweet women that just had no chemistry with, some pretty, some plain, some I'm still friends with.
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