Friendship, fun, more? How do I find out?

October 22, 2009 6:08 PM

You're a late 30's, attractive female who is separated and looking to explore your horizons. How would you like to be approached by a younger couple?

I am the male, older half of a couple who are quite...libertine. We are open to new people and new experiences, including bringing others into our bedroom. I guess you could call us "swingers," though it doesn't happen often - we aren't usually very forward, we just let things happen naturally.

I have been going to a particular medical office for almost two years, and have chatted with a woman who works there quite a bit. During my last visit we talked about her situation, being separated from her long-term partner and moving out to her own house. Also we talked about my girlfriend and I, what we like to do, and that we're more open and liberal. I also mentioned going out, and that she should come out with us, that we would "show her a good time."

On leaving, she handed me a business card with her cell number written on the back. At this point I assume that she is interested, but this is uncharted territory for me. I'm not usually forward, and I haven't been in this situation before.

Since both my girlfriend and I are open to this, but don't really know how to approach it, my question is: If you were this woman, how would you like to be approached? Something like calling her and saying hello, and asking her out for drinks one evening?

I'm not 100% sure she had the same idea we did, she might just be looking for friendship, so I don't want to embarrass her or myself (and my girlfriend). Any advice you can give on how to delicately approach the situation would be appreciated. I wouldn't mind seeing her as a friend, but I got the impression that she was open to more, since that was the direction the conversation was headed in, and we had talked quite a bit in the past, with no numbers being exchanged then...only now that she is separated and on her own...

Strangely enough, I am a bit nervous about calling her for some reason, and am not able to think rationally about what is probably a very simple solution. Anyway, thanks in advance!

posted by anonymous to Human Relations (17 answers total)

It seems like the cautious way to go would be to approach her as a friend, go out with her and your girlfriend, and see how the interaction goes. I imagine it would become fairly clear pretty quickly if everyone is on the same page - plus, that will give her and you girlfriend a chance to see whether or not they have any chemistry, which I would imagine is important.
posted by you're a kitty! at 6:26 PM on October 22, 2009

Call her and propose to meet in a neutral, but intimate setting. You and your girlfriend should pick the place first, and that's where introductions will be made. Discussing it with your girlfriend will ease your nervousness too . You don't want a restaurant meal, but you don't want a busy club, either. Maybe a restaurant bar. Some small joint where alcohol is served and where there will be minimal table between the three of you. Music that is not tasteless or loud. Subdued, but not dim lighting.

After a few drinks things will happen naturally. Do you like to dance? That'll help. A lot in fact. But it's not nessecary. Hop a few bars as you get more comfortable as a threesome and move on from there. :)
posted by clarknova at 6:26 PM on October 22, 2009

Speaking as a someone who has, within the last two years, been 30 something and recently divorced I would be at least flattered if not interested. Yeah, call her up for drinks and do the same kind of thing you do on a date i.e. test the waters by talking closer and closer to the subject. At some point you are probably going to have to just come right out and ask or confirm that you are talking about the same thing but if she already has some idea of your preferences she is probably not going to freak out. At worst you find out she is not interested and at best... well, the possibilities make it worth trying right?
posted by stubborn at 6:27 PM on October 22, 2009

She may be trying to read you for the same signals that you're trying to throw out there. OR, she may just be intrigued by the promise of some flirtation. Or she may not be sure, but is a little curious. But since she's already given you her card and expressed interest in socializing outside of her job, invite her out.

A good way to get through the awkwardness is to just admit it. "Okay, I'm feeling a bit oddly nervous but hey, my girlfriend and I agree that it would be fun to hang out you. Wanna make plans? We were thinking of going to [location]. Why don't you join us?

Make it casual and escapable and convenient. And then once you're there, engage in the normal smalltalk and conversation and see how things go. (I'm presuming that if you two have done this before, you know the drill regarding it being your girlfriend to escalate with the affection rather than you.)
posted by desuetude at 6:31 PM on October 22, 2009

You should all get together for coffee, or an afternoon glass of wine with no intention of taking it any further.

Hang out. Chat. Get to know each other. Find out what the chemistry is. When you find that everyone gets along well, and you've hung out a few times, then you can broach the idea of having her over to stay the night.

When and if you do ask, you should be clear about your intentions. You don't have to be crass, but don't be coyly vague by asking for "dinner followed by..dessert" or something equally cheesy either.
posted by device55 at 6:32 PM on October 22, 2009 [1 favorite]

I've been approached twice by couples (both younger, but not by much). It wasn't something I was interested in, but one couple freaked me out while I found the other's approach flattering.

Couple One: I knew the male half better than the female half, and considered him a friend. We wound up at the same party, were dancing, having a good time. The female half of the couple started getting handy with me. I was startled, realized that they were both expecting me to leave with them, and wound up hiding from them for the rest of the party.

Couple Two: I'd met the female half of the couple at a semi-regular social event, and got along well with her. At the next event, she brought her boyfriend and we wound up chatting for several hours, laughing and enjoying ourselves. The female half said to her fella, "See, isn't she great? I told you you'd like her." When he agreed, they both turned to me and smiled. She leaned forward and said, "You should totally have a threesome with us." As I was with Couple One, I was startled. I looked from her to him, back to her again, and when it was clear that I wasn't answering in the affirmative, they giggled, I giggled, and we started chatting again. While I didn't go home with them, I did go home feeling like a rock star.

I'd go for the "let's hang out" approach and - if it feels comfortable - be direct. You can always laugh it off if she's not into it.
posted by pammeke at 6:49 PM on October 22, 2009 [3 favorites]

For some reason I used to be a magnet for these couples. Wasn't really interested in any of it, but personally I always found it significantly less creepy/threatening/uncomfortable when the woman propositioned me than when the man did. When the male half of the couple is the one pushing for the threesome it just feels much skeevier, probably because there are a lot of abusive men who coerce their wives into doing sexual stuff they don't want to. So then you have to wonder if the wife is really into it, or if she's just playing along as part of her victimization.

So my advice is for your wife to be initiator, not you.
posted by Jacqueline at 8:19 PM on October 22, 2009 [1 favorite]

I came in to say the same thing, that the threesome propositions come better from the female in the couple. I've only been approached a few times, but as a woman I feel like it is less threatening and that you feel more comfortable when you feel the woman is a fully enthusiastic partner, not like the guy is leading the whole situation.

Drinks or dinner is good. I'd say meet somewhere and progress to your place if/when things go well. She will be more nervous if she goes to your house without ever meeting your girlfriend, and might feel pressured just for showing up at the door into doing something she isn't ready for yet.

Also, definitely bring up the idea in speech before in deed, as Jacqueline suggests. Light, teasing, flirtatious, "We should totally do this..." and then allowing for a reaction works much better than getting physical right away.
posted by misha at 8:30 PM on October 22, 2009

There's one thing that concerns me about this that nobody else has mentioned yet...

"I have been going to a particular medical office for almost two years, and have chatted with a woman who works there quite a bit."

There's an expression "don't shit where you eat." I think this falls into that boat. If you want to pursue this, and it gets awkward (and with these things there is always the potential for that), is that something you will be comfortable with next time you go back to this office and run into this woman?

And put yourself in her shoes. Lets say she had something else in mind and you spring this on her and she freaks out. Now she has to keep seeing you at the office for the duration that she works there.

That said, if you still want to pursue this I'd advise getting a bit friendlier first to feel her out (not up). If you can casually present her with some situations that are related to your intentions and get her to comment, you might get a read on her reactions. Like if there's a funny movie the three of you can watch that has a threesome scene or joke in there. Maybe crack a comment about it about how fun it is and see how she responds.

Or you can pop the question with a smile and if you can read people quickly, just laugh it off right away if you detect a negative reaction.

I had couple friends do this to me once (I'm a guy) and they laughed it off too quickly because I would have said yes--but felt they weren't serious at that point and didn't want to suggest it myself.

Agreed with having it come from the girl and also, do your best in every way possible to give her the impression that you are trustworthy people who know how to keep private about these sorts of things. If she's curious but nervous, she might decide against it due to fear of the secret getting out. Maybe introduce her to another female that you've had a threesome with in the past and let them get friendly and have her broach the subject to gauge her response.
posted by Elminster24 at 9:20 PM on October 22, 2009

Lets say she had something else in mind

She almost certainly had something else in mind. When he said, "You ought to come out with my wife and me, we'll show you a good time," chances are virtually nil that the medical office worker thought he was talking about sex.

This is definitely a "don't shit where you eat" situation.
posted by jayder at 10:00 PM on October 22, 2009 [1 favorite]

I suggest pursuing someone else, for the reasons described above. The ideal situation is likely to be someone who does not work at your doctors office, and someone who your partner has more of a connection with than you do (initially). It seems possible, but unlikely that this current situation will work out the way you hope.
posted by serazin at 10:02 PM on October 22, 2009

Switch medical clinics now. Have all your records transferred and your account at the current clinic closed. Then hang out with the woman as a friend. Then think about whether to propose a threesome. Please ask this woman to make a decision about getting sexually involved with a client of the practice where she works. At best, it'll be grist for the office rumour mill, because someone will find out. At worst, it could get her fired on ethical grounds. On preview: Jayder's right, don't shit where you eat.
posted by embrangled at 12:13 AM on October 23, 2009 [1 favorite]

Gah, unfortunate typo! Correction: please don't ask this woman to make a decision about getting sexually involved with a client of the practice where she works.
posted by embrangled at 12:14 AM on October 23, 2009

Strong third for the advice that you remove yourself from her professional sphere first (embrangled gives you nice clear instructions above) before considering approaching her for sex.

That element makes this not primarily even a multi-partner question. Instead it's a "should I proposition somebody with whom I'm in a client-practitioner relationship" question (the answer being "Dude... no").

If you do remove yourself from the client-practitioner relationship (and remember, even then something of it still exists in past tense): I've been approacher and approachee in this context and I agree with the casual-happy-hanging approach described by several posters above. (Especially misha and Elminster24's advice that the actual propositioning's gotta come either primarily from your girlfriend or equally from both of you at the same time in the same place.) Have fun if it works out, and remember, safety first!
posted by kalapierson at 1:13 AM on October 23, 2009

I'd hang out with her and show her a fun, wild night out without propositioning her. Show her you can be fun people to be around, and try to wingman/wingwoman for her a bit if she's interested in that. By being fun and flirty around her she'll get more happy around you and see you two more like supportive, friendly, and awesome people and less like people who only want her for one thing (I assume that since you've been friendly with her for two years you actually would be interested in being friends with her and supporting her a bit through the rough patch & through reassembling her identity as a single person?).

Then, after you've shown her a fun, wild time out without propositioning her, ask her out again. The second time can be a more intimate setting. She'll know you two are fun and will be excited to hang out again, and personally once she's seen y'all get down with each other on the dance floor and generally show her an awesome fun night out, I think you've got a better shot at her thinking you'd be fun to do more intimate things with. Plus, if she's not interested, you've already established that you two and she can have fun doing other things - like just hanging out and being her wingwoman and wingman at the bar with no pressure.
posted by lorrer at 6:34 AM on October 23, 2009

In general, be prepared to look for a while. On the polyamory mailing list that I used to belong to, there were two terms for the sort of person that you're looking for. One was HBB, as in Hot Bi Babe, and was a fixation of swingers who signed up for the list for one reason and one only. There were a lot of couples looking for HBBs, and the degree of success that they had could be gauged by the other nickname for HBB: unicorn.

Nthing that this woman could be reading something completely different into your interaction. Depending on the particular details of the separation, she may be estranged from a lot of her friends as well as her partner. If it turns out that that's not her thing, well, she may be completely cool about it in your future interactions, or she may be really, really hurt. Switch your doctors or look elsewhere.
posted by Halloween Jack at 7:49 AM on October 23, 2009

Switch medical clinics now. Have all your records transferred and your account at the current clinic closed.

This hadn't occurred to me, but at most professional offices --- medical clinics and law offices, and perhaps others --- staff getting involved with a patient or client would be grounds for immediate firing of the staff member.

And a patient propositioning a staff member would certainly be a strong reason to ban the client from the clinic.
posted by jayder at 8:25 AM on October 23, 2009