CasualSex-filter: I am a straight woman. I'm not into the bar/club scene whatsoever. I've never had casual sex, and want to change this. Tips for doing this as safely as possible? [more inside]
posted by anonymous on Dec 14, 2009 - 14 answers

I'm part of a short-term couple. We both know it will probably end in about six months from now, due to a long-distance move. I feel that there's a multitude of things I can experiment with here, due to the short-term nature of the (non?)relationship. But what are those things? Also: I know that each relationship is different, but what are the general rules of such relationships, anyway? How am I supposed to be in love, without falling in love? What can I do to make the most of the time we have left? [more inside]
posted by anonymous on Nov 9, 2009 - 16 answers

How do you phrase "are you into me?" in a non-terrifying way? [more inside]
posted by anonymous on Oct 25, 2009 - 22 answers

Your tips on figuring out my feelings as I enter into casual play relationships? (risque elaboration within) [more inside]
posted by anonymous on Oct 4, 2009 - 10 answers

How to tactfully break things off with a woman I just started dating? [more inside]
posted by anonymous on Jul 12, 2009 - 45 answers

I smoke a cigarette a day during the work week. I've been doing this for a few months now. Am I going to die of lung cancer? [more inside]
posted by anonymous on Jun 18, 2009 - 33 answers

How long is too long of no contact while dating? [more inside]
posted by anonymous on Apr 21, 2009 - 32 answers

I am 20 years old and male. There is a girl (19?) in my circle of friends who really, really, wants to have sex with me. She hangs on my every word, and I get the impression I can do no wrong in her eyes. She's a nice enough person (and pretty smart to boot), but I'm not interested in a romantic relationship with her (or at all, really). She asked me out, and I politely declined, and a few weeks later she straight up offered to have sex with me no strings attached (again, politely declined). That was a month or two ago, and now I'm thinking of taking her up on it. I've never had sex, despite situations like this having played themselves out two or three times before. I find her quite physically attractive. My fear is that no matter how bluntly I say "I just want to have sex with you", she'll pine for a relationship, and I'll be leading her on. Should I do this? How?
posted by anonymous on Apr 3, 2009 - 61 answers

I always thought I'd wait for someone special to have sex for the first time. But I haven't met anyone special. Is pursuing a casual relationship a good idea, and how do I do it? [more inside]
posted by anonymous on Feb 2, 2009 - 24 answers

I want to stop being a relationship-machine and start having something more casual. Why do I get attached so quickly? And how do I prevent myself from getting attached so I can have more fun? [more inside]
posted by anonymous on Dec 23, 2008 - 24 answers

I've become involved in another unhealthy relationship. What do I do, and how do I avoid it next time? [more inside]
posted by anonymous on Nov 19, 2008 - 23 answers

How do normal people go about finding casual sex? For someone who thinks that taking advantage of drunk girls in clubs is immoral and adult match-making websites are scams or dangerous, is there any outlet to meet nice (albeit frisky!) gentlemen and ladies? [more inside]
posted by anonymous on Jun 20, 2008 - 20 answers

Peripatetic, endearingly-awkward geek seeks amazing advice for casual sex shenanigans. [more inside]
posted by anonymous on Dec 18, 2007 - 113 answers

Is there a website (preferably free of charge and community-driven) where people go to safely arrange one-night and/or casual hookups? [more inside]
posted by anonymous on Oct 12, 2007 - 18 answers

Just found out that my long time love is a daily phone sex participant and while away on a business/pleasure trip (staying with friends whom I spoke with on the phone) is posting and responding to online "casual sex" posts for both men and women. I don't know if meetings occured. [more inside]
posted by anonymous on May 8, 2007 - 32 answers

Where -- in South Central Wisconsin -- are the best places to hang out, if you are a divorced, middle age, overweight, woman who recently decided to proactively search for short term companionship? [more inside]
posted by anonymous on Mar 9, 2007 - 20 answers