Threesomefilter: How does a couple pick up another woman?

June 3, 2009 1:33 PM

We'd really like to have a threesome with another woman. Where do we even begin?

My girlfriend and I have a wonderfully healthy and relationship. We’ve been together for almost four years, we are very in love, we have great sex, etc. We also openly recognize that we both have fluid sexual orientations (i.e. we openly discuss our bi/poly tendencies) and we’ve both had varied sexual experiences in the past (i.e. sexual relations with each sex). We’re also both very sexually open, love sex, love being close to other people (I know I know…this sounds like we’re a couple of hippies, but in fact we are young professionals who simply enjoy physical pleasure).
We’ve been discussing having a threesome with another woman for some time. We are both comfortable with the idea, have talked about boundaries and comfort levels, etc (we have also discussed having a threesome with another man, but have decided to start with a second woman). The problem is: how do we make this happen? I read a poll recently that 60% of women in my area (I live in the Pacific Northwest) are open to the idea of group sex. Is this actually true? Are most women open to the idea but are simply too inhibited or can’t find the right couple? How do we find someone interested? Is this something we can just “bring up?” – like at a bar?

We are REALLY hesitant about using things such as craigslist or adult friend finder. We’d much rather meet someone, get to know them a little, have it evolve organically – simply because we aren’t old pros at this sort of thing and we want the women we take home to an interesting person, good conversation, want everyone to feel comfortable and no pressure, etc. We’re not looking to date them, per se, but we are also not interested in just soliciting sex off a website from a total stranger.

Part of the problem is that I have a really hard time “hitting” on women. I always feel that, no matter how genuine I am, I will simply look like a douchebag. I’m a guy who thinks about 98% of all the women I see are completely beautiful and I would love to tell them so, get to know them. But I’m shy and constantly afraid she’ll think I’m some creep. So what do we do? We can’t just approach a random woman we meet and say, “hey, you’re really beautiful and you look really nice…can we buy you a drink?” Or can we? Is that weird? How would we tell another woman that we are interested in her sexually when clearly we’re a happy couple? Do I let my girlfriend do the talking?

Does anyone have any experience with this? If it helps, we’re in Portland, Oregon, mid-twenties, attractive enough, not into anything extremely kinky or crazy, sexually adept but not very experienced in this arena.

posted by anonymous to human relations (41 answers total)

We’d much rather meet someone, get to know them a little, have it evolve organically – simply because we aren’t old pros at this sort of thing and we want the women we take home to an interesting person, good conversation, want everyone to feel comfortable and no pressure, etc.

I really think this is as easy as socializing together and cultivating a healthy air of receptivity. And yes, you CAN just bring this up with someone at a bar. If you've had a pleasant evening and have been chatting with someone and you and your wife have exchanged "the signal", there's really nothing wrong with saying, "How would you like to continue this conversation at our place?" Trust me, she'll probably get what you're hinting at. What's the worst that can happen? She'll say no.

I think the results you're going to find online will probably be every bit as disappointing as you'd imagine.
posted by hermitosis at 1:46 PM on June 3, 2009

I can tell you that most of the people looking for threesomes online are couples. You do the math.
posted by sunshinesky at 1:46 PM on June 3, 2009

I think the virtue of things like Craigslist and AdultFriendFinder is that those sites (as well as real-world communities centered on swinging) allow you to just get it right out there, the fact that you're looking for a woman for a threesome.

In the face-to-face world, it is virtually impossible to come up with a way to broach this so that you don't look like sleazy pervs.

If you meet someone and let it evolve organically --- starting with a friendship in which she really likes you and your girlfriend --- what if she's massively disgusted with your proposal? You invested time in cultivating her as a friend, and then you ended up looking like a manipulative jerk who only befriended her to groom a potential threesome partner.

I think that, even in the most enlightened, forward-thinking parts of the country, most people will find your proposal off-putting and will think you're a creep if you propose it to them in a face-to-face setting.

Caveat: I have absolutely no experience in this realm, nor any interest, by the way.
posted by jayder at 1:48 PM on June 3, 2009

How do you (or how have you, in the past) hook up with someone for casual one-on-one sex? How does your girlfriend (or how has she, in the past) hook up with someone for casual one-on-one sex?

You do more-or-less what works for you in that context, just doing it together (and it's best if she takes the lead in approaching potential partners, because that lowers the potential squick factor a lot).

And you expect a lower rate of success, because you need to find someone who a) is into the idea, b) finds your GF attractive, c) finds you attractive, and who a) your GF finds attractive, and b) you find attractive. That's a lot of variables, so the odds of making a connection are lower.
posted by Sidhedevil at 1:57 PM on June 3, 2009

Caveat: I have absolutely no experience in this realm, nor any interest, by the way.

No need to make this caveat, it shows in your answer.

Generally, in MOST places, respectful propositions from someone with whom you've established a friendly rapport are not going to transform them into a "sleazy perv" right before your eyes. If someone's not interested, they're often still rather flattered or amused. What's more likely than being regarded with disgust is being regarded with fascination -- people who turn you down will often be very curious about your relationship and want to know more about how you ended up this way together.
posted by hermitosis at 1:58 PM on June 3, 2009 [5 favorites]

I have to respectfully disagree with hermitosis... Depending on the person, their background, etc. they COULD be so freaked out at the concept that you would turn into a "sleazy perv". But hopefully since you are talking about cultivating friendships first you would get a feel for that long before propositioning her

But yes, the prudish, Puritan views of relations does still exist, even in Oregon.

Then again there are the more risque-minded people who WOULD ask more questions even if uninterested.

That said, AFF, Craigslist, etc. aren't like brothels, you can meet like-minded individuals there and get to know them first and see if you hit it off. At least then you're being very upfront with what it is you're looking to get out of the relationship.

But given what you've said, I'd suggest the club route first.
posted by arniec at 2:09 PM on June 3, 2009

Dan Savage always says to avoid hooking up with friends and instead hire an escort. I'm pretty sure there are escorts who specialize in this sort of thing, and that it would be fun.
posted by KokuRyu at 2:10 PM on June 3, 2009 [2 favorites]

No need to make this caveat, it shows in your answer.

I know that I and most people I know would (a) not be interested, and (b) probably be too uncomfortable, from that point on, to remain friends with the proposer.
posted by jayder at 2:12 PM on June 3, 2009

Forget the club route. Try FetLife.
posted by arimathea at 2:14 PM on June 3, 2009

Your local alternative rag (Willamette Week and their ilk) likely has classified ads that deal with this.

You can be as selective as you want, and take as much time to vet as you want. Just be prepared to say, or hear, "no" in a graceful way if, upon meeting, the vibe is not there for you or the other woman.
posted by Danf at 2:19 PM on June 3, 2009

I feel like almost every time I go to a burlesque club, no matter how conservatively dressed I am or how little I'm feeling it, a couple propositions me for a threesome. So, uh, try a burlesque club? At least you know upfront that a female customer's idea of a fun time can involve watching naked girls, and she's probably more sex-positive than average to boot. (For the record, I'm bi -- and apparently someone's picking up on that wavelength -- but threesomes and random hookups aren't my idea of fun.)

Also, if you let the girl approach while the guy goes to get everyone drinks or something, it's less creepy. The girl, like me, may still decline politely -- but she's less likely to be skeeved out.
posted by booksandlibretti at 2:23 PM on June 3, 2009

Think of it this way, if you've got the stones to do a threesome, you ought to have the stones to get rejected quite a bit. Get out there in a bar, start introducing yourself and your girlfriend, buy some people some drinks, and see what happens. Maybe people are kinkier than I think they are.
posted by jayder at 2:24 PM on June 3, 2009

Get out there in a bar, start introducing yourself and your girlfriend

Have the girlfriend do the introductions. Seriously, this makes all the difference in the world. If the girlfriend approaches, you (potential 3rd) don't feel like she's just going along with it grudgingly.

I feel like almost every time I go to a burlesque club, no matter how conservatively dressed I am or how little I'm feeling it, a couple propositions me for a threesome.

Yes. Basically, any unescorted women in any setting where women are disrobing (burlesque show, strip club) or scantily dressed (nightclub) is automatically assumed to be interested in a threesome. So that might be the easiest place to start; worst case scenario, you'll blend into the static.
posted by Sidhedevil at 2:29 PM on June 3, 2009 [1 favorite]

Louis Theroux episode on swingers
posted by acro at 2:30 PM on June 3, 2009

Asking someone face to face might be easier in a vacation destination. I find people to be more open to this sort of thing when they don't have to go home and clean or go to work the next day, like its a vacation from their normal sex too. So maybe take a nice tropical vacation this summer?
posted by WeekendJen at 2:36 PM on June 3, 2009

I think that, even in the most enlightened, forward-thinking parts of the country, most people will find your proposal off-putting and will think you're a creep if you propose it to them in a face-to-face setting.

Only to people who are so opposed to threesomes that they're incredibly narrow-minded about the sexual exploits of others. Yes, you'll probably hit on a quite a few women who ultimately aren't interested, but I doubt you'll deeply offend them by essentially admitting that both you and your girlfriend are into them. The novelty of the request and the additional presence of your girlfriend usually mitigates lots of the sleaze inherent in just a dude asking a lady to go home with him. Maybe I've been in enlightened, forward-thinking New York for too long, but most of the resolutely monogamous women I know here would be flattered at the very least by such a proposition, if also a bit flabbergasted.

I'd suggest having your girlfriend approach these women and strike up conversations with them first, and then you can join if they seem to have decent chemistry. Then both of you can subtly flirt with the lady in question while also making no secret about your status as a couple. Honestly, I've been propositioned before and this is the point when it's possible to guess the couple's intentions before they hash out their proposition. Do this at a bar, but not one you frequent all the time. Do this after two drinks, but not six.

The burlesque club suggestion is fantastic idea.
posted by zoomorphic at 2:39 PM on June 3, 2009 [2 favorites]

Your girlfriend should be the one doing the talking. If you take the lead in 'hitting on' women for the both of you, the probability is very high that you'll be dismissed as skeezy ("Oh yeah, my girlfriend's totally into it too, trust me").

Initiate your face to face interactions at clubs or sex-positive events. Steer the conversation in risque directions to gauge the comfort level of your new friend--if she plays along, she may continue playing... And again, let your girlfriend lead. Women can easily pick up on flirtatious behavior from other women, even if they're as outwardly innocent as compliments or briefly touching an arm. For a bi-curious woman entering into a threesome, having a connection with the woman is likely the most important variable for her. If the evening goes well, your girlfriend could propose a little three-way kiss good night.

Don't write off the online options--as stated above, it removes the 'is she open to it?' question, but you'll have to sift through many profiles to find her.
posted by oceanmorning at 2:39 PM on June 3, 2009

I know that I and most people I know would ... probably be too uncomfortable, from that point on, to remain friends with the proposer.

If you've met someone at a bar and hung out with them for an hour or so, it's not like you've invested a whole lot into becoming "friends" with them anyway. Which makes it especially easy for both you and the other party to move on to other people if rejection is on the menu.

If you're talking about someone whom you've met and hung out with a few times, how is this different than if you met another single person, whom you thought of as just a friend, who turned out to have feelings for you? It's just the risk we take as social, sexual creatures. It sounds like you'd consider these advances to be calculated or predatory in nature, but for most people that's just how we get to know people. If, after certain facts have come to light, you decide you don't want to know this person, it's not the end of the world for either party.

My partner and I have had the best results in situations where one of us has individually struck up friendships with someone and invited them to some upcoming social event where so they can meet the other partner. This is a pretty standard invitation to extend whether you are interested in someone sexually or platonically. At that later point, when they've met the other partner, if the judiciously correct amount of flirting has taken place, it becomes pretty obvious to everyone involved where things are headed. Some people are amazingly forthright, others are a little more coy and want to be wooed. Some fade from sight, either not making the connection or not being interested.

The best part about all of this strategy is that it's not a scheme to make sex happen -- it's a scheme to broaden our social circle and explore the vibes that we get from different people. The fact that this sometimes results in sexual encounters is an exciting and important feature of our networking as a couple, but it's not our main agenda. If someone reacted with disgust, I wouldn't take it personally -- everyone has their own hang-ups. But a polite demurral is the worst thing we've ever encountered, and as long as we continue to behave like real, thinking, feeling people then I can't imagine that will ever really happen.

Anonymous, I don't know how open you plan to be with your friends about this feature of your relationship, but you should know that word tends to travel -- in a good way. Curious people on the periphery of your social circle may approach you independently if they've heard that you're tastefully, discreetly in search of folks to experiment with.
posted by hermitosis at 2:45 PM on June 3, 2009 [2 favorites]

If you go the Craigslist route: please do NOT post on w4w. The regions I've seen, you'll get reported to hell and back instantly, because that is just not what people are there for.
posted by restless_nomad at 2:45 PM on June 3, 2009 [1 favorite]

Dan Savage always says to avoid hooking up with friends and instead hire an escort.

When trying something new and potentially dangerous, it can be helpful to have professional there to minimize potential difficulties.
posted by Brandon Blatcher at 2:46 PM on June 3, 2009

I'm sure Portland has a few sex positive orgy parties. Just go check one out and see if its your scene. Its a place full of people looking for the same thing you are (possibly), and there is no obligation to do anything but look around. I know quite a few couples (in NYC) that are in to polyamorous stuff and they do the parties - also a good way to just build a community of friends and acquaintences that are interested in threesomes, etc.
posted by RajahKing at 2:48 PM on June 3, 2009

Yes. Basically, any unescorted women in any setting where women are disrobing (burlesque show, strip club) or scantily dressed (nightclub) is automatically assumed to be interested in a threesome.

I kind of disagree with this -- in my experience, a burlesque club's atmosphere is totally different and considerably better (funnier, classier, more enthusiastic, more "rah rah third-wave feminism") than a strip club's. And I'm not sure I've ever gone "unescorted"; it's usually with a small mixed group. But despite my nitpicking, I obviously can't disagree with your conclusion that it's a good place to start.

Anonymous, I'll go into a little more detail -- this is how, in my experience as a HBB/unicorn/whatever, it seems to work there:

The couple hangs back a little, checks out the crowd, points out cute girls to each other. When you find someone you agree on, the girlfriend happens to find a place near that girl. Between performers or sets, the girlfriend strikes up a friendly conversation that turns flirty if the solo girl is receptive. I'm usually just going from "Oh man, is this girl flirting with me? She can't be, can she?" to "She is! This has to be flirting! How did she know?" when the guy comes in.

He says something about the line for the bathroom, gives girlfriend a quick hug, girlfriend performs introductions, maybe a minute or two of conversation before guy offers to buy a round and heads off for the bar. Girlfriend says something indirect, along the lines of "oh, my boyfriend John's a great guy, he's so much fun . . . and, you know, it's an open relationship." If solo girl says something noncommittal or otherwise makes it obvious she's not totally on board, hey, you've had a nice conversation and made a friendly acquaintance, and you can always move along to another girl. If solo girl is receptive, I'm assuming you play by ear with more flirting on all sides when the guy returns. If you still wanted to get to know her better before acting on anything, you could always invite her to a quieter bar that allows for more talking, or to street drunkfood (crepes, falafel, etc.), before your place.

This is obviously not a strict script; it's just the smoothest version I've had run on me (by a vacationing couple I later saw leaving with company). Just going up to a girl and saying "hey, beautiful, how about a drink and then a threesome?" is probably not a great idea whether it's you or your girlfriend doing the asking. Because then, yes, you'll come off as weird or creepy.
posted by booksandlibretti at 3:04 PM on June 3, 2009 [7 favorites]

Someone I, ahem, know has been swinging for four years and has had precisely two threesomes involving two women. Both were bad experiences. Why? They rushed into bed with the first girls who were interested in the both of them. Both women turned out to be large bags of crazy. They've learned since then (and this is a gross generalization, so grain of salt) that in their geographical area, single women seem to be single for a reason. They opt instead to stick with other couples instead, who are by far easier to find and hook up with. Memail me if you want to know more.
posted by theraflu at 4:51 PM on June 3, 2009

I kind of disagree with this -- in my experience, a burlesque club's atmosphere is totally different and considerably better (funnier, classier, more enthusiastic, more "rah rah third-wave feminism") than a strip club's.

I agree with you, and yet I think it makes zero difference to the "woman on her own must be looking for a threesome" frequency, except that the people who hit on you are considerably more appropriate about it. At least this is my experience (also as a bi woman).

But now I'm confused--didn't you just say that every time you went to a burlesque club you got hit on by couples? Because that's my experience too, but now you seem to be disagreeing with that premise. Am I just lost in a migraine haze?
posted by Sidhedevil at 5:06 PM on June 3, 2009

This bi girl/former unicorn sez: Listen to hermitosis, booksandlibretti and Sidhedevil (and the others who actually have some idea/have had some interest or experience in this realm.) And yeah, the girl does the intro.

Sidhevdevil, I took booksandlibretti to mean that the equivocation of burlesque with "any place women are disrobing" was a bit off. I.e, you get approached by couples in both places, but the vibe sure is different.
posted by desuetude at 6:40 PM on June 3, 2009

For the first time, hiring a professional (escort) is by far the easiest. It's a monetary transaction, all the boundaries are clear, you can set the mood and the terms beforehand and call it off if it's not going well - and it's safe.

Second easiest is sex parties and 'getting-to-know-you' nights in your area - here in London we have fever parties, which offer full-on swingers parties (for vetted couples and single women) but also women-only nights for women to get to know each other. Google around for what's available where you are.

Picking up strange women in bars is hard, paticularly if you don't run with the e crowd (it's always easier to pick up if you're all on drugs). Otherwise, getting drunk with a close friend who you think might be receptive is your best bet, but you have to be really frickin careful about seeming predatory, as it may ruin your friendship. Professionals are safest and easiest.
posted by goo at 7:07 PM on June 3, 2009

For the first time, hiring a professional (escort) is by far the easiest. It's a monetary transaction, all the boundaries are clear, you can set the mood and the terms beforehand and call it off if it's not going well - and it's safe..

Not exactly hottest, though. And gives you no real experience on how to ever hook up with someone for whom it is not a monetary transaction. Look, no offense to pros, but, I don't personally know any couples who are actually into threesomes who have gone this route. And it doesn't seem to jibe with what the OP is looking for, either.
posted by desuetude at 7:23 PM on June 3, 2009

Oh for sure, desuetude - notice I said easiest and safest. Hot is what you make it - and sometimes you just have to accept that your fantasy of picking up a beautiful woman in a bar for a threesome is just not going to come to fruition, so why not hire a beautiful woman whose job it is? Partlcularly if it's your first time and you're nervous...

I've been on the receiving end of this transaction too (er, minus the professional element!). It requires a lucky conflagaration of all the elements when you involve a stranger, and the vast majority of the time the proposing couple just comes across as skeevy.
posted by goo at 8:15 PM on June 3, 2009

My best friend and her husband recently made a successful transition to swinging. They also wanted a threesome with a woman, but ended up:

1) Meeting only long term couples who are out of their twenties (to minimize any glomming-on/emotional crazy)
2) Using craigslist & contacting the best combination of attractive but "normal" seeming couples
3) Starting with a coffee date to see if everyone is comfortable and interested
4) Taking it easy on the first go-around (just fooling around)
5) Plenty of debriefing -- they even found a book at the SF public library which helped them deal with the emotions/marital issues that arose because of their new activities

Maybe they planned it out more than a lot of people would, but I've got to say - their bond seems strengthened & they're still having a f-ing good time.

Good luck!
posted by jenmakes at 8:39 PM on June 3, 2009

they even found a book at the SF public library which helped them deal with the emotions/marital issues that arose because of their new activities

I wonder whether it was The Ethical Slut... I found that book to be slightly dated but really genuinely helpful.
posted by hermitosis at 9:34 PM on June 3, 2009

Seriously, if Dan Savage told people it would help their relationship/sex life to jump off a cliff, I think a lot of people would. Anyway, I'm going to go against the "gospel" (or is it the GGGospel) and say that he is wrong. Don't hire an escort. Having this type of sexual experience for the first time will probably be less stressful if there isn't money involved. Meeting someone and clicking will probably be better.
posted by ishotjr at 9:50 PM on June 3, 2009

I think the book was "Redefining Our Relationships: Guidelines for Responsible Open Relationships" -- though I see the library has a few other titles on the subject including The Ethical Slut... I heart San Francisco!
posted by jenmakes at 10:09 PM on June 3, 2009

Someone I, ahem, know has been swinging for four years and has had precisely two threesomes involving two women. Both were bad experiences. Why? They rushed into bed with the first girls who were interested in the both of them. Both women turned out to be large bags of crazy...

This.

So, your girlfriend should meet a girl first, and introduce you, then you hang out for a while. After you've hung out a bit and you're all getting along (don't force it, if it isn't working let it go), you vamoose with an excuse and she raises the question of whether the girl is straight, gay or bi. Come back after that conversation, and then see if you're all still having a good time. Have your girlfriend get her number for future hang-outs, then touch base on whether you'd both like to see her again. If you agree, then you (not your girlfriend) call her up and see if she's out for a date, "just the three of you." If she accepts, you can proceed from there.

disclaimer: I never took this approach myself -- although had the crazy people experiences -- but one other person I know who is a woman and into threesomes says this is the kind of vibe she looks for
posted by davejay at 10:12 PM on June 3, 2009

All of the three/more-somes I've been involved in have been with friends, but it's possible that sort of thing wouldn't really fly with your friends group. Most have been good, some have been great, and none of them have resulted in excessive angst or awkwardness. Also, all but one of them were unplanned.

I guess my friends are all sex maniacs.

YMMV, a lot.
posted by darkshade at 7:20 AM on June 4, 2009

hermitosis et al., Tristan Taormino's newish book Opening Up is the less dated answer to The Ethical Slut. It might be worth a look for the OP too, actually.
posted by clavicle at 8:08 AM on June 4, 2009

i agree with jayder... grooming someone is creepy - having sexual intentions towards someone that might think you are a monogamous couple and therefore can let their guard down is borderline manipulative. it is not bad, per se, but can take someone off guard and offend them.

this works: go to a lesbian bar in your town. when a couple shows up at a girl bar, the gals there get the picture and any gal into the two of you will make it known. you can approach people in such a setting and even if there is a "no thanks" there are never any hard feelings... or creepiness.
posted by babsomatica at 10:56 AM on June 4, 2009

Babsomatica, I don't know what lesbian bars are like in your town, but the ones I've been to you'd have a 50/50 shot of getting interest or getting run out of the bar by a horde of angry women who are pissed beyond belief that you've intruded on the ONE PLACE they can go to to NOT BE HIT ON BY MEN. That's pretty much the attitude I was referring to above, about Craigslist W4W.

Me, I don't like those odds. But then, I'm also one of the people that would be at least mildly pissed off by being approached by a straight couple in either of those settings.
posted by restless_nomad at 12:17 PM on June 4, 2009 [2 favorites]

For Portland and Seattle: See The Stranger's & The Mercury's Lustlab personals. I've not personally used the site, so YMMV.
posted by whycurious at 2:52 PM on June 4, 2009

If you're in Portland, just go to Aces (now known as Angels).
posted by mullingitover at 4:56 PM on June 4, 2009

Ugh, no, please don't go to a lesbian bar and try to pick up. I'd put the odds at 5/95% likelihood of failure and pissing off the clientele. As restless_nomad notes, dyke bars are meant to be safe spaces and that usually does not include honouring the fantasies of random straight couples. Please respect that.
posted by goo at 6:28 PM on June 7, 2009 [1 favorite]

I've had a few threesomes with a particularly open minded female friend of mine (we're JUST friends, with obviously some benefits). I'm a guy. On each occasion, I had very little to do with the actual hooking up. Twice was in "regular" bars, once was in a strip club. I guess it makes it easier that we are "just friends", but each time, it wasn't a planned thing, I just let her go do her thing, she met some interested woman, they spent some time together (maybe a bit of girl on girl kissing), then I get introduced, and I basically just tagged along from there on. My friend had already sussed out whether it was worth introducing me to the mix, so it was all very easy for me.

If you're girlfriend is at least a bit outgoing, let her lead. She'll probably be a lot better at it than you. Let her be a bi girl who has an easy going boyfriend, and see how she goes. Don't get jealous. Find someone else to chat to yourself, let her do her thing, wait in the wings, and let your girlfriend choose the time to introduce you.
posted by Diag at 8:15 AM on June 9, 2009