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

Should I ask this girl to a date this summer? If so, how should I ask? [more inside]
posted by Thisispiggy on Mar 31, 2012 - 14 answers

You're a smart, awesome guy with serious social anxiety. What's the least awful way a friend could let you know they have feelings for you? [more inside]
posted by anonymous on Dec 11, 2011 - 35 answers

I think a friend of mine may have feelings for me, but I'm not sure how all that works nor what to do about it. Can you help a romantically clueless girl in the right direction? Details below. [more inside]
posted by anonymous on Oct 27, 2010 - 18 answers

I didn't think the whole "if you're persistent it'll work" thing would work, but it did and now I have a chance to get to know her better...what do I do? She's gorgeous and smart...now if I can just get her to laugh some more with me, I'll be on the right path. Or do I boast, or compliment? [more inside]
posted by talljamal on Jul 15, 2010 - 25 answers

How do I properly initiate contact with a person who dumped me because he thought I may not sexually accept the way he is? How can I let him know that I'm the same way too? [more inside]
posted by anonymous on Oct 14, 2009 - 13 answers

I saw something I wasn't supposed to see and now I'm not sure how to deal. [more inside]
posted by anonymous on Sep 25, 2008 - 39 answers

What is the best paid dating website with ACTUAL results? [more inside]
posted by wildrain2008 on May 17, 2008 - 25 answers

How can I get over my confidence issues and find a girlfriend (or boyfriend) in Ft. Wayne, Indiana? [more inside]
posted by thirteenkiller on Feb 18, 2006 - 30 answers

Am I wrong for being angry at my friend? [more inside]
posted by skjønn on Nov 17, 2005 - 65 answers