David Letterman confesses on national TV.
posted by blue_beetle on Oct 2, 2009 - 269 comments

Everyone has been in bad family photos, but sometimes a photo goes beyond bad and becomes awkward.
posted by WinnipegDragon on May 8, 2009 - 77 comments

A catalog of unfortunate moments in maleness courtesy of Awkward Boners (NSFW).
posted by hermitosis on Apr 30, 2009 - 107 comments

Haven't got your fill of awkward rap? Well there's Bill Cosby's upcoming rap CD and a new dance joint about a beat down. Or you can reminisce and revel in 13 awkward rap commercials of old. Not enough? Okay fine, how about a freestyle battle. [more inside]
posted by cashman on Apr 16, 2008 - 37 comments

An Awkward Situation Flirting strangers suddenly find themselves a little closer than they wanted to be. Have you ever been in an awkward situation with a not-quite-stranger?
posted by oissubke on Oct 16, 2002 - 39 comments