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Online Dating: Beyond Vanilla

I'm getting back into the dating world after a long-term relationship went south. I've never dated online before, but now I think it's time to give it a try. I've looked at a few of the sites, and they either seem too uptight (eHarmony) or way too kinky ( Craiglist looks interesting if from no other reason than it's free. My question is what is the best way to find a mildly kinky, sane, woman for a long-term relationship on Craigslist? Is it even possible? Are there other places I should look?

You asked for an opinion. Here are three.
Divide & Conquer
Bide Your Time
Cast a Wider Net for Better Fishing

You said in your question that you are looking for a woman to date, though you didn’t reveal your own gender–I hate to assume you’re straight, but it is likely, specifically because you didn’t mention it. I’d like to say orientation doesn’t matter in online dating, but in the Craigslist world, it does. The gay boy boards (m4m) are rarely used for anything but immediate hookups, and the lesbian areas (w4w) are filled with bisexual hookups, men trolling, and, on occasion, real dykes who are quite successful. Many dyke couples I know met on Craigslist, and I have had some success in finding playdates and occasionally dating and friends on there.

But the straight m4w or w4m boards? Honestly, I have no idea. But, regardless, you will have fifty times more luck finding a “mildly kinky, sane woman for a long-term relationship” on Craigslist if you post your own ad rather than respond to any. Women who have posted ads will probably get dozens (at least) of responses – the burden would then be on you to prove yourself as a worthy suitor. But if you post, you will be the one to get the responses, and you get to take your pick. Women who are posting are probably also reading, so don’t worry that you will miss someone. This isn’t to say “don’t respond” – certainly, if you run across an ad that is incredibly appealing, go for it. It’s worth a chance.

One more bit of advice: try posting two ads. In one, describe yourself vaguely, and give one or two characteristics you like in a girl. But keep it very open and vague, saying you’re looking for fun, flirty dates, and to see where it goes. In the second ad, be very specific: describe what you want and what you like. This is where you say “mildly kinky, sane woman for a long-term relationship.” These are two different approaches to dating, and someone who might be intimidated by that scary "long-term-relationship" phrase might still hit it off perfectly with you, and the two of you can then ride off into the sunset together.

One last thing: don’t only meet people on dating sites. The Internet is a big place, full of people connecting with each other. Go anywhere you can have an authentic exchange about a topic you care about – running, sports, your favorite band, wine, or other hobbies & activities – and talk to the people who are involved in those communities. is a social networking site by topic: check that out. Look for other discussion boards  or social sites where you can jump in and, if nothing else, practice flirting.

Good luck!

Sinclair Sexsmith

Sinclair Sexsmith

Sinclair Sexsmith is a sadistic kinky queer butch top who writes about sex, gender, and relationship adventures at Sugarbutch Chronicles. He partners with femmes and gets off on intentional identities, gender theory, feminism, chivalry, and whiskey.


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Be open, honest, detailed, and use OkCupid

As a (more than mildly) kinky and (mostly) straight male who's been using online dating sites for years, I've had lots of online connections that went nowhere, but one mind-bogglingly perfect match that makes up for all the rest, and I'd like to make some specific suggestions to the questioner which might also help other people.

First, the site I have had the most luck with is, which asks everyones lots of questions about themselves and what they want in a partner, and then ranks people by match %.   This means that it's real easy to find people who have a lot of common interests and values, without having to sort through lots of chaff.  While not tailored to kinksters per se, one of the ratings it gives people is 'Kinkiness', and I have had far more success meeting kinky folk who want real relationships on OkCupidthan I  have on, say, or alt.   And best of all, it's free, which means it has a huge user base, including lots of 'mildly kinky' women who would never put up a profile on a kink dating site.

Second, I recommend writing a relatively lengthy profile that gives people looking a very accurate idea of who you are and what your looking for - including, say, the very question you posed to the perv panel.   While this may mean that quite a number of women will look at it and be turned off, those aren't women you'd want to get into a relationship with anyway - whereas, anyone who *does* like what they read is someone you'll probably get along with.  Definitely include a pic or two.  And from talking to many female friends about their online dating stories, I can guarantee that profiles are one place where longer is *definitely* better.

Third, once you have a really nice and open and honest profile up (and on OKC,also answered a few hundred questions so matching works), *then* go search for women with high match percentages and profiles you like.  When you find one, just shoot off a quick little email saying hello, you liked her profile, then let her take the initiative of looking at yours and deciing of she wants to reply.  make sure your use correct spelling, punctuation, and grammar; be very polite; giive some indication that you actually *read* her profile and this is not a generic letter; and don't tell her how hot she is.  It says something about the world of online dating that, according to all the women I know, that style will make your message *really* stand out from majority.

Finally, check back in on your profile at least once a week, and update every month or so, even if nobody has responded.  Most sites rank profiles by how recently their owners logged in, with the most recent ones at the top.  If you don't log in regularly, your profile will slip to the bottom, and even if someone does happen to like it, they may be leery of contacting someone who hasn't been on the site in months.  Whereas, if you log in regularly, women doing seraches will keep seeing your profile up at the top - and as every advertiser knows, the more people who see your ad, the more people are likely to respond it.

Now, I can't promise that this will lead to you finding the girl of your dreams, even though it did for me.  But I can tell you that when, after a year or so of being off the dating sites, I went back and updated my various online profiles as in the manner I describe above, within a few weeksI was contacted on OKC by a handful of *very* compatible women.  One of those women is now my primary partner, is more compatible with me than any other woman I've ever met in 30 years of dating (and as I said, I am way more than 'mildly' kinky), and said that the writing style, humor, and level of openness I displayed in my profile was totally what caught her attention.

I can only hope that my experience helps others to do even half so well. :)

Galen Douglas Zimmerman

GalenZ on,, and

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Perv Panel
July 6th, 2009
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CarnalNation has assembled twelve people, whose diversity is matched only by their perversity, to form the Perv Panel. Each week, three of our resident perverts tag-team your most intimate questions...