What are some good date options in Pittsburgh?

You helped me find Mexican Coke... now let's see if you can help me find a sweet date place!

EDIT:

Some more info: Both 22. She's artsy and into musical things. I like them, too, but not to the extent she does Any season is good, but fall/winter ideas are appreciated. Driving isn't an issue, I work in Lawrenceville and live 15 miles north of there. Under $100 would be ideal, but I'm still open to other suggestions!