I've gone to the shows, I've taken the classes and I've gotten used to the feel of a solid belly laugh. If you're looking to switch things up on a Saturday night, head on down to the Glass Nickel on Atwood and catch yourself some improv. The MBI troupe is a mish-mash of top notch talent offering both family friendly and late night shows. The downstairs setting at Glass Nickel for the shows is intimate and prime for getting you slightly out of your comfort zone. The beer you can down during it also helps with that too.
And when you're done watching one of the shows, get on stage yourself as you consider dabbling in the variety of classes they offer. The classes are a bit pricey but they're more than willing to accommodate with multiple payment options. Both Brad and Jason are fabulous teachers, devoted to taking the intimidation out of improv comedy one awkward audience recommendation at a time. I'm now in the process of completing level 4 (they have 5 core level classes) and am considering signing up for the music special topics class this summer. I didn't think I could get any more hilarious than I was but surprise, surprise.*
*Classes do not teach humility.