Where's a cool place to take a 37 yo girl out for a date that has live entertainment outside of Philadelphia?

552 Restaurant in Newtown would be perfect. Voted most romantic in Bucks County. Live entertainment on Friday nights and probably the best outdoor dinning in the area. Fantastic food. It's like being at a city restaurant. http://www.552restaurant.com/

It depends--are you going up to where she is, or is she coming down to where you live? If you don't mind going all the way up to New Hope, Havana's on Main Street is pretty nice. Their music schedule is on their website (havananewhope.com), and they often have dancing. If you want to meet halfway (and don't want to go into Philly), check out the Main Line, Plymouth Meeting, or King of Prussia area. Milkboy Coffee in Ardmore always has live music, so does Kildare's in KOP. The Main Line now has First Friday events, which always involves music and culture on the first Friday of each month (http://www.firstfridaymainline.com/). Phoenixville has the Steel City Coffeehouse and a few other places, but I think that might be too far for you. Manayunk isn't *technically* the city, and there are plenty of places there for food & entertainment. Friends of mine often play at Grape Street, and I think there's live music at the Brew Pub.

How far do you want to go? There is always a lot of good food and entertainment in Atlantic City, but it is about a two hour drive from there. Of course, if you can rent a limo for the evening and share her company as you are driven to and from, that could be a whole great experience, too.