26. Participate in the Santa Speedo Run
See: Chicago Polar Plunge.
27. Do an all-you-can-drink special
Offered at a few sports bars around town -- like Kelsey’s and Durkin’s -- a Friday all-you-can-drink special offers bottomless domestic brews and pub grub, and a chance to show your liver who the boss is. Shut up, liver!
It’s difficult to maintain your dignity when you’re yelling at unresponsive turtles in a bar that’s so packed that you’re basically standing inside someone else’s pants the whole time. But that doesn’t mean it’s not fun.
29. Go to a DIY venue show
Seeing live music is fun. Seeing live music in a dingy house is really fun, but it’s less fun when you’re overdressed and everyone around you is probably still in art school. So, go when you’re still young. Where? Ask your one friend who wears jean-jacket vests. They’ll know.