9 posts tagged with awkwardness and dating.
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What to do when someone at work asks you out

And you like the person but you're seeing someone [more inside]
posted by winterportage on Dec 8, 2015 - 21 answers

I'm dating-challenged and dropped the ball. How I do pick it back up?

Over last weekend I spent a whole bunch of time with a lovely woman--dinners, picnics, walks, wine under the stars etc. These weren't explicitly dates, but it all seemed pretty romantic. At the end of the evening on Saturday and Sunday we had these awkward pauses when my insecurities and my desire to--give a goodnight kiss? Express my attraction? Or something--were warring. I don't know what she was thinking but it was awkward on both sides. Now I won't see her for a month. Do I email her and explicitly say that I'm interested? [more inside]
posted by anonymous on Aug 26, 2013 - 25 answers

Talking: How does it work?

I've been seeing my boyfriend for about three months, and just about everything is great. We see each other almost every day and sleep at each other's houses so often we practically live together. We have everything in common, and I've never met anyone I click with that much. One thing we have in common that's not so great, though: we're both shy, and sometimes we don't know what to say to each other! How can we overcome this? And, while we're on the subject, what are some good conversation starters? More info below. [more inside]
posted by Gee, June! on Feb 27, 2013 - 39 answers

How can I encourage more open communication with people?

Help with encouraging communication early in a relationship? [more inside]
posted by randomnity on Jan 2, 2013 - 6 answers

How should I handle this somewhat awkward dating situation?

How should I handle this somewhat awkward dating situation? [more inside]
posted by freem on May 23, 2010 - 31 answers

How do I turn a one-night stand into more?

How do you turn a particularly enjoyable one-night stand into something more? Lots of overanalysis and fairly NSFW details inside. [more inside]
posted by anonymous on Feb 2, 2009 - 7 answers

explain to me this... mojo.

Please explain the basic principles of flirting to me as if I were an alien who had recently landed on Earth trying to describe the phenomenon for my anthropological records or something. [more inside]
posted by anonymous on Jan 23, 2009 - 27 answers

I like you, but not, like, LIKE like you.

Meeting and making friends from online dating sites? [more inside]
posted by anonymous on Aug 26, 2007 - 14 answers

UGH!! I'm no Demi Moore

Paging Mrs. Robinson: How should a lady gracefully discourage a Bright Young Thing who seems to have formed an inappropriate crush? [more inside]
posted by lonefrontranger on Jul 4, 2006 - 56 answers

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