I got to see him about 5 years ago now at Zanies in Rosemont Illinois. I don’t think I ever laughed as hard for as long as I did for anyone else. He was so funny and he went after everyone. There were parts during his show where I had tears coming down both sides of my face because I was laughing so hard and I couldn’t barely breathe. The woman I was dating at the time was absolutely horrified at his comedy and I think she was the only one there who really had no idea who Gilbert Gottfried was or what he was like. That was our last date together. And I still laugh about how funny he was that night and how lucky I am to have found out what that woman was like before things got serious. I really enjoyed her company until that night LOL
Its pretty impressive that Gilbert was banned from the Howard Stern Show being too offensive.
I wouldn't take a date to see Steve Wright, unless she said she was interested. He's not offensive, but either you "get it" or you don't.
I imagine nothing is longer than a date seeing standup with a woman who doesn't like the humor.