I must say that the following was the funniest I've heard in a while...
The Instigator (while walking to Her Majesty's Theater in London to see Phantom of the Opera and dressed accordingly in nice clothes): "I look like a n00b in this gear with these white socks."
(To those that don't understand the significance of this, it is a World of Warcraft reference, in which he is pretty much obsessed with constantly upgrading his gear, which is what he referred to his [dark colored] clothes and black shoes as. Yes, I think this is indicative of a needed break from gaming, though it's not likely to happen...)
Matt (sitting around the table at Elphaba's house after dinner): "Do you want a washing machine to try dyeing in?"
Me: "Actually, I think I'd like to live a few years more...."
(That one is probably more of a "you had to be there" moments, but it was still pretty funny!)