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 (alt.com). 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?
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. Ning.com 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.
Sinclair SexsmithSinclair 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.
I'm afraid there is no easy answer to your specific question: "What is the best way to find a mildly kinky, sane, woman for a long-term relationship on Craigslist?" While it is likely that amongst the many people posting for relationships on Craigslist, there is at least one woman whom you would find attractive, with personality and goals that complement yours, and with a compatible interest in kink, it's also possible that there isn't. You just won't know until you meet the person.
Craiglist, or any other on-line posting site or dating site, is, ultimately, nothing more than a modern, higher-tech version of the personals people used to (and still do) place in weekly newspapers and the like. It's just a way to help you meet people – and since you can't really know what you're dealing with until you get out and meet that person IN PERSON, you just can't know what you are dealing with... Sure, you can believe that maybe posting online is a little better than newsprint personals because you might see a picture, and it's easier to initiate an arms-length dialogue with someone thanks to e-mail, but ultimately, it's just one of the many ways to help you come in contact with candidates.
While I do know of some people who have met their life partner online, I know of none "first-hand." I tried polingl some folks who have used Craigslist and other listing services for dating, but no one had any real specific advice. So I'm going to take this opportunity to answer what I think is the more important question: how can you get into a relationship with a woman who meets your criteria? I think your real issue is that you would like a long-term (possibly permanent?) relationship with a woman that you can connect with on many levels and who has a high level of sexual interest with more-than-just-plain-vanilla curiousity or tendencies that are compatible with your own. Perhaps I'm projecting my own relationship values into your question, but that's how I read your situation.
This may sound trite, but I suggest that the following will serve you better: be patient and spend lots of time doing the things you love to do. You are most likely to meet a suitable partner in the environments that are most natural for you. Sure, cruise the on-line listings, too. There's no reason not to try and increase the number of people you meet, but I think that overall you will meet more people who are like you in the places you like to be than by trying to interpret someone's e-posting and photo.
When you have met someone (whether through "real life" or online) and if there are hints of physical chemistry, bite the bullet and have a frank conversation with that potential intimate partner about some of your sexual preferences and kinky ideas. Try to learn about theirs while you're at it. This doesn't have to be a "super-serious" conversation, but if you don't explore your new hottie's potential for a little kink BEFORE you jump in the sack a few times, you may get into a situation where ANY sexual contact makes it more difficult (as it does for most of us) to not get drawn in, more connected, etc. And if THAT happens and your new sexual partner, with whom you may even have had some really great sex, ultimately does not want to "play" as much as you do on the kinky side, then you will again be tied into a relationship that doesn't satisfy you, at least sexually, and you will have to decide if the other positive attributes outweigh that. The fact that you have posted this question indicates that someone's rating on the Kink Index is indeed an important factor for you.
Essentially, I freely confess that I'm using your question to get up on my soapbox about hopping in the sack with hotties when you say you are looking for a long-term relationship. There is nothing wrong with having great consensual sex with someone you've just met. BUT... If you are looking for a long-term relationship, then there are usually many more variables in play than just the sex. And since sex (especially good sex) has a way of clouding the perception of those other issues in the initial attraction period, it's generally prudent to take a relationship a little more slowly when you want it to turn out to be a long-term one. And to be willing to walk away from it if it turns out that it will disappoint you in the sexual or any other category. If kink and sex-play are important for you, then it is of the utmost importance to really explore your new potential partner's interest in those things before you get too intimate. If she's the right woman, such a conversation is very likely to get her really turned on anyway!
In closing, I commend you for identifying what's important for you, and I'm certain that the woman you are looking for is out there – in fact, I'm certain there are many excellent women, any one of whom will be a great partner for you. But again, you must be patient yet open to a possible relationship. She will arrive in your life right when she is supposed to... it'll be your job to identify her correctly and then sweep her off her feet.
Straight ManStraight Man is married, very happily so. In his waking hours, he is functionally and often ravenously heterosexual. Though neither a top nor a bottom ("Well, just what IS he, then, dahling...?"), he can be highly aroused by mild BDSM scenes and freely engage in, enjoy, and take pride in fantasies involving virtually every kinky and erotic possibility out there, including the standard array of multiple partners and genders. He also deeply cherishes the partnership he has, so his real-world sexual and erotic activities remain within the bounds agreed upon for that partnership—which is to say, firmly rooted in monogamy. Nonetheless, Straight Man has had many long years of success working at strong and open dialogue about all issues sexual and erotic, and he hopes to bring all of this bedroom (and other venue) experience to bear in the Perv Panel discussions to come.
Certainly it's possible to find someone online for a night or for a lifetime — in fact, I met my partner through an e-mail discussion group in the late 1980s, well before the advent of the web!
There's really no best answer about where to look, but casting a wide net increases your chances of finding what you're looking for. It's become a cliché that if someone is into any unusual kink or fetish, there's someone else out there who shares it, and you can find them on the Internet.
Many of the mainstream dating sites, as you've discovered, can be pretty staid. There are a bunch of sites aimed at the BDSM community (Google is your friend!), but you might have better luck with the free online personal ads from more general publications aimed at open-minded people -- like Nerve.com or The Stranger (which offers both a vanilla and a kinky version). Or look for sites that cater to your non-sexual interests: Geek 2 Geek, Green Singles, Atheist Passions, etc. A lot of people have found each other through Craigslist, which has the advantage of focusing on specific geographical areas. (See their helpful safety tips for meeting a prospect in person.)
The trick with online dating — like doing it in the physical world — is making contact with a lot of people in order to find the few that click. Try narrowing your criteria from "mildly kinky" to something more specific. For a long-term relationship, of course, look for someone with a compatible lifestyle and shared interests beyond sex. The process isn't necessarily any easier in cyberspace, but it's a big sea with a lot of fish!