Where Ryan told Ashley he loves her for the very first time (a couple big-ass margaritas deep, of course)! Spend some time in Shadyside while you are there - Walnut Street is full of great shops and bars.
If you are in the mood for a bar crawl, the South Side is where it's at! Start the night at the Flats, where Ashley first told Ryan she had "feelings for him that start with an L." Don't be mistaken - this is by no means a chill or romantic experience. Only come here if you want to party. To put things into perspective - the only reason Ryan would have been caught dead here was in pursuit of Ashley :)
The absolute BEST restaurant in town. End the night with some brews at Cinderlands for the full Ashley and Ryan date night experience.
One of Ryan and Ashley's favorite places in the city to grab a beer! Located in the Strip District, where you can find a mix of gourmet food shops, street stands, and many bars and eateries.
If you have never been to Pittsburgh, you have to take the incline up to the overlook - you will get the best view of the city and a great photos!
Trying to get out of town? Take in some fresh air at McConnell's Mill State Park. Beautiful hiking trails, if you're into stuff like that...