Help me decide whether, and how, to man up with a shy friend I like-like with a significant age gap. Cue the snowflakes. [more inside]
posted by hungry hippo on May 4, 2012 - 35 answers

Met guy at party, friends with him on facebook...how to get in contact with him? [more inside]
posted by skybluesky on Dec 29, 2010 - 12 answers

How many times does one ask a girl out? [more inside]
posted by isoman2kx on Mar 10, 2009 - 40 answers

AskingOutFilter: I've heard of a potential match from a third party.. how might I go about acquiring her contact details (or other info) in an uncreepy way? [more inside]
posted by Quarter Pincher on Feb 1, 2007 - 17 answers

how do i say this: "i like you and that other night was great, although slightly weird because you're my friend's really close cousin, but he seems cool about it, so, anyway, do you want to do that again sometime, even though it's been a month since that night?"- without coming across as wanting to be too serious or too casual or too weird? [more inside]
posted by twirlypen on Feb 14, 2006 - 11 answers