Movies – Boring. Taking your date to the movies will make her think you are boring; that you are too boring you can hardly sit for a few hours alone with a girl for a conversation. See, the movie gives you an excuse to skip the talking and save it for when you take her home (if she lets you). It’s something a dorky high school boy would do on his first date with his middle school crush or something – where he hopes they end up holding hands at the very least or making out a little at best. If you’re going to take her to the movies, at least wait til the second or third date to do it. That, or at least make your choice of movie and movie theater impressive.
Wine Bar – Ooh, fancier than a fancy restaurant. You are either very topnotch or pretending to be and trying to suck up to your boss. So, you’re a higher level of elite (wannabe) than the fancy resto guy. The line that separates the classy and the pretender is how well you know your wines and cheeses. If you choose this place, might as well take a crash course in wines.
Diner or Fastfood - Cheap. No girl gets impressed at a diner for a first date except maybe if you could get the cooks and waiters to sing her a lovely medley of Frank Sinatra’s or Nat King Cole’s. Or at least anything awesome like that.
Fancy restaurant – you are the I-wanna-impress-her-but-I-can’t-think-of-anything-else. Well, the fancy, candlelit dinner type with some operatic music on the violin is playing in the background is very classic, but not thought of enough. Impress her with how well you know the menu and your table manners or die trying on the caviar.
Picnic in the park or fishing by the lake - Adventurous and wants to impress that way. You may strike her as the romantic kind, loving nature and all, but at least make it a comfortable experience for her. If you end up feeding her to the mosquitoes or making her starve after hours of not getting a catch, or feeding her with picnic food that’s less than palatable, then you may be un-thoughtful.