I'm not embarrassed by any of the music on my iPod, but people tend to be puzzled when they hear "How Deep Is Your Love?" by the Bee Gees play...
Item of clothing? I've got a Thunderbirds (the bad movie from a few years ago) t-shirt
Thing you've done on a date? I peed off the side of Suicide Bridge (Colorado St. Bridge)
I'll stop answering now, as I'm not sure of the statute of limitations
