Not casual sex, but not not casual either.
September 21, 2009 8:09 PM   Subscribe

How do you handle sex, in regards to dating a couple of people at once? (I'm a dude, for the record)

I was starting to write a ridiculously long version of this question that wasn’t making any sense. So I’ll assume you know where I’m at when I’m asking it. I’m internet dating. I’ve done it quite a bit. In the past, I would sort of go out with anyone that moved. I’ve become much more selective about who I’lll go out with. So lets say for example that everyone I meet likes me and I like them, and we want to go on more dates.

Say also that I’m staggering meeting women based on schedules, so that sometimes, if I’m writing back and forth to 3 women, I might meet woman A on a Monday one week, have a 2nd date the Monday of the following week, have a first date with woman B on the next Tuesday, a first date with woman C on that Friday.

Basically: I’m equally emotionally involved in 3 situations, trying to get to know 3 women, and not be a jerk to any of them, or to myself.

So if I make it to date 3 or so with woman A, and intimacy starts to enter the picture, do I slow things down and explain that I’m also getting to know B and C? Do I say, hey, I’m into this physically and I want to do it, but you need to know there is B and C too? Or do I say, well, time to decide what to do about A, and whether I’d like to go with door B and C instead of A? Or something else.

I'm not on a 3 date=sex schedule. But sometimes it happens. This kind of thing also makes me nervous on dates, and I'd like to find a way to feel relaxed and honorable about the whole thing.
posted by anonymous to Human Relations (21 answers total) 10 users marked this as a favorite
I am a woman, FWIW.

Unless you are exclusive with someone, it's really none of their concern who else you are dating. Be responsible and use protection, but don't think that because you're having sex with A, you can't also sleep with C.

But don't sleep with two women on the same day. That's just... no. That, in my eyes, would make you a jerk. So would making promises of exclusivity to A, but continuing to sleep with B and C. If you are unattached and feel no desire to become exclusive, sleep with all three if you like. I, personally and again as a woman, could never bring myself to date or sleep with more than two men at a time. But that's just me.

Also: if any of these girls start to fall for you and you're not into it: do not continue to sleep with her. She will only get hurt.

Good luck!
posted by caveat at 8:19 PM on September 21, 2009 [3 favorites]

First and foremost - wrap that rascal. Feeling relaxed and feeling honorable may be mutually exclusive. It really depends on how much you value honesty in a relationship. Personally, I wouldn't feel "honorable" without being totally honest about concurrent endeavors. I would, however, feel "relaxed" by doing multiple chicks.
posted by torquemaniac at 8:25 PM on September 21, 2009

Depends what you want, depends what she wants. Ask if they're looking for an exclusive long-term thing or a casual shag and some good company every now and then. And do it quickly because with three girls involved, regardless of how well-intentioned you are and how respectably you handle it, one or more of them is going to be hurt no matter how it pans out. It could be Tub-Of-Chocolate-Ice-Cream hurt or it could be Gonna-Fuck-Up-Your-Car hurt or it could be On-Tonight's-News-Another-Jumper-On-The-Golden-Gate-Bridge hurt.
posted by turgid dahlia at 8:33 PM on September 21, 2009 [5 favorites]

Also, if you're planning on not being exclusive with someone, let them know that from the get-go.

I'm not a woman, but if I were being intimate with somebody I would want to know if there's someone else currently in the picture. It might not be their concern who else you are dating, but it's most definitely their business that you're dating someone else. I've run across no end of scummy swingers (not intimately, but seen from the sidelines) who didn't do that and ended up really hurting someone when they suddenly sprang the news after a month of sex that hey, they've got another boyfriend.
posted by dunkadunc at 8:50 PM on September 21, 2009 [15 favorites]

Make sure none of the women know each other...
posted by melissam at 9:02 PM on September 21, 2009 [5 favorites]

If you're going to be sleeping with more than of them (and by "sleeping with," I mean any contact with one another's genitals. Refraining from intercourse isn't a loophole.), you need to tell each of them that she is not the only person you are having sex with.

If you decide not to be honest with them, make sure that any woman you end up having a relationship with doesn't find out that you didn't tell her. I can't speak for all women, but I can tell you that I know many women who would break up with a guy if she found out that he had slept with anyone else after they started sleeping together, regardless of whether they were "exclusive" at the time, and regardless of how long they'd subsequently been dating. I've seen it happen. It's a dealbreaker for a lot of women.

In other words, your first and best option is to be honest when it comes to having multiple sexual partners. Your second, and in my opinion, inferior option, is to lie forever to any woman you begin dating this way.
posted by decathecting at 9:09 PM on September 21, 2009 [8 favorites]

Just a random comment: If you're going to sleep with multiple people at your place, change your sheets between them. Not doing so is disrespectful.
posted by sinderile at 10:01 PM on September 21, 2009 [2 favorites]

Definitely be honest at least about the fact that the others are in the picture. Personally, that would be a dealbreaker for me and it would save us both time getting that out of the way early.

As others have mentioned, any sexual activity has a potential to spread disease, so if it gets physical with one and you haven't told the others by then, that's the time to do so.
posted by cmgonzalez at 10:09 PM on September 21, 2009 [3 favorites]

Another vote for telling them you're still seeing other people. You don't have to be specific about it or anything - just say that, while you're dating with a view of starting an exclusive relationship with the right person (if you are), you're not yet ready to be exclusive with her. I think for a lot of people, sex implies exclusivity. If that's not the case for you give the woman the choice as to whether to wait or whether she's fine with it. If it were me, I would wait and see what developed first and would only want to have sex when I knew it was exclusive. A lot of women (not all, but I happen to be one who does and I'm sure there are others) have trouble separating sex from emotional connection. Having sex with you on Monday and then seeing you out on a date with another woman on Tuesday would really hurt!
posted by hazyjane at 11:05 PM on September 21, 2009 [4 favorites]

I would say, don't do it. However, I have done it so I'm not a moral authority.


1. Dating more than one person feels ok; there's nothing criminal about having two different coffee dates per week. Having two sexytime dates per week feels a bit like you're having your cake and eating it.

2. Having the 'are we exclusive' conversation during Date #2 is a real mood killer.

3. If you end up falling for Lady B, both you (and she) might feel bad in hindsight for sleeping with Ladies A and C because how could you possibly have thought they were The One etc etc. It's like being faithless in advance.

FWIW, I'm a girl - and while I did do it, I ended up with three boys who assumed I was interested in pursuing a longterm relationship with them alone, which I wasn't. Even the guy who knew the situation ended up getting a bit clingy despite his assurances to the contrary. Conclusion: it's too much hassle.
posted by citands at 2:40 AM on September 22, 2009

Why not mention that you're not connecting sex with exclusivity, unless you thought it would make her change her mind about having sex with you?

And if it would make her change her mind about wanting to have sex with you, shouldn't you mention it?

Be honest, and let her make her decision from there. Hiding something from someone in order to make them more willing to have sex with you is ick in general.
posted by palliser at 5:30 AM on September 22, 2009 [2 favorites]

I hope you realize that no one can give you a hard-and-fast rule for this. Lots of people will have opinions based on their own experiences and values, but the only way you're going to find out how the women you're dating feel about it is to talk to them about it. Personally, I always assume multiple interests/partners on the part of people I'm dating, until we discuss whether the relationship will become exclusive. But a) that's not everyone's assumption, and b) everyone has a different threshold for when that discussion needs to happen.

So discuss it with the women you're dating. Definitely let them know from the start if you have emotional attachments elsewhere (doesn't sound like this is the case for you). Make it clear whether or not you're interested in having an exclusive relationship in the long term. If an exclusive relationship is your dating goal, let your partners know as soon as an emotional attachment develops. And while sex=exclusivity is not the assumption I operate under, I think hazyjane's advice that the conversation about non-exclusivity should happen before you have sex with any of them is sound.
posted by EvaDestruction at 5:32 AM on September 22, 2009 [1 favorite]

I think that you should make it clear that you are dating other people or are thinking or dating other people until you get to know the person....You dont have to say what you are doing with other people or even how many people you are dating or will date. At the end of the day you are seeing your options and trying to decide the best one and two or 3 or 4 dates is not enough to know whether you should be exclusive with someone. You've already tried the part of being in relationship with whomever gave you a chance....this might work for you after some time and allow you to find out exactly what you need from other partners.....If you are dating three people I think its possible that one of the girls will not go with this scenario but probably not all three of them........

Use protection, be discreet, and at the same time honest with yourself and your partners....
posted by The1andonly at 7:02 AM on September 22, 2009

I found that it was just easier to avoid multithreading women like that. One at a time worked for me.
posted by Citrus at 8:02 AM on September 22, 2009 [4 favorites]

Honorable? What exactly are you aiming to be, a four star general? Hell, even Patton slept with his niece.

Question your aims rather than your method.
posted by fairykarma at 10:09 AM on September 22, 2009

As you can see, you have to do what you think is right.

If you decide not to be honest with them, make sure that any woman you end up having a relationship with doesn't find out that you didn't tell her.

Be careful of the subliminal moralizing in that sentence.

It not "not being honest" to be discreet.
posted by Zambrano at 10:54 AM on September 22, 2009

My feeling is that bringing up involvement with other people too soon could potentially be insulting and put a chill on romantic feelings that would otherwise develop. This is probably a scenario where ignorance is preferable to a point. I would say that point is sexual contact, due to health risks for everyone involved.

Also, if it does come up, you should absolutely be honest. I just don't think you need to offer that sort of information on a first or second date because bringing it up unbidden is kind of like saying, "you're not that important to me". People should know that intellectually, but it doesn't mean they'd enjoy hearing it.

In other words, I'd keep mum about other people unless your date brings it up, or you want to go past second base.
posted by Cogito at 1:16 PM on September 22, 2009 [2 favorites]

If you are simply dating, then I don't think there is a problem with maintaining multiple relationships. However, if any of these relationships become sexual, I think you have a personal responsibility to let the others know - regardless of the fact that you are acting responsibly in regard to contraception.

Since you are asking the question, I suspect that you know what the RIGHT and PROPER direction you should take. STDs are transmitted in ways other than the simple penis-to-vagina interaction. If the other girls are cool with it (Who knows? Maybe they are also "seeing" other people.), then so be it. You were honest and now you need not worry about hurt feelings. If they aren't, then you need to make a decision.
posted by murp0837 at 1:18 PM on September 22, 2009

I pretty much agree with everyone else in this thread. Unless you and A, B, and C are all openly polyamorous, I wouldn't recommend sleeping with more than one girl you are seeing, period, because if they find out, There Will Be DRAMA. Juggling and "nonexclusivity" really only works out of the poly community well as long as nobody is getting groiny. Once people have to be phobic about who they're going to catch STD's from, it's a whole new ballgame.
posted by jenfullmoon at 3:44 PM on September 22, 2009

So, what's the difference between dating 3 women serially over the course of six months, and dating 3 women simultaneously over the course of six months? Is that a sure-fire way to avoid hurt feelings and DRAMA? This has not been the case with people who come crying to me about their love lives.

Do you really think it's more "honest" to have an exclusive "relationship" with someone for six to eight weeks, break up with her, and then run the cycle again with the next woman, and then next? Honestly, I never know what people are talking about when they tell me they just "broke up" with someone they have only known for a month or two. Really gives me a "hey you kids, get off my lawn" feeling. (And makes me all "quote-y" to boot.)

Plus everything caveat and Eva Destruction said.

You are an adult. Live your own life. If people seem to be assuming things, set them straight.

And by the way, there will be people who don't want to continue unless it's exclusive - that's their right. Just like it's yours to say no to that. (And if they come back later, saying oh yes, upon reflection and not having sex with you, they can handle it, you might want to take that revision with a grain of salt and keep them in the friend zone.)
posted by Lesser Shrew at 9:17 PM on September 22, 2009 [1 favorite]

The way you wrote this, it all sounds fairly hypothetical... which to me means you're over thinking this.

On many occasion I've worried over similar things (oooh, should I invite them both to my party? or, I slept with my ex but what do I do with my new beau tomorrow... etc) only to find out that 99% of the time, things don't work out like that. (even though I´ve wished they would... !)

You know?

Don't have sex on the first date, just make out. By the time you've gone out with each of these women, you will have a good idea of who you want to get closer to.

I think it's highly unlikely that all three are going to be equally interesting and attractive to you and feel the same degree about you.

Just play it by ear and don't say things you shouldn't, and yes, try to be honest when needed.
posted by Locochona at 4:08 AM on September 23, 2009 [3 favorites]

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