I'm a tall Irish guy living in the Philly suburbs who is sick of the same thing. I'm a guitar player of 15 years. I live comfortably, but work my ass off to get it. Through what I've seen on here, a few things translate in girl-speak, (such as: "I go for older, more mature guys..." translates to "I'm looking for a rich stock broker to buy me expensive things...") so if you're one of those, don't bother. I'll take care of a girl best I can, but can't promise you the world. What I CAN promise is: good times, spontaneity, etc. I've been told I'm a stereotypical guy; I like football, drink beer, drive a truck, and like working outside. If you want some dude that pops his collar, highlights his hair, and spends more time in front of the mirror than you, I'm not your guy.
Ideally it would be to a laid back restaurant for some good food, then to either the best movie in the theaters, or anywhere fun like laser tag, a concert, etc....i know it all sounds cliche, but I'm not big on planning things. I take them as they come.