Sex and the Sixties Girl: Can You Sleep With Two Men at Once?

Before you read any further, let me assure you that this is not a piece about threesomes. And I’m not even asking you to answer the question posed in the title. I’m merely repeating the name of a section in Sex and the Single Girl on affairs. After posing the question, Helen went on to tell us of a 30-year-old, very fabulous-sounding friend of hers who was having sex “on the front seat of convertibles with twenty-year-old college boys” and “on yachts with dashing old men” as well as in “boarded-up summer cottages” and “unfamiliar bedrooms while a party was raging downstairs.” The friend’s most recent conquests, as of the book’s writing, included a “famous young actor” and “a blind date who’d made up a fourth for bridge.” At bridge!

I stand back in admiration of this woman.

Many, perhaps, don’t. Many—even in our modern day, post Sex and the City time—may think she sounds downright slutty.

But I just wonder how on earth she was able to manage such a situation, in her era or any other. Most women I know couldn’t maintain such a schedule for the sole reason that sleeping with a man does something funny to their vision: it prevents them from being able to see others, let alone consider sleeping with them, let alone sleep with them.

For me, it’s actually even more extreme than that. I don’t even need to be sleeping with a man for others to be rendered invisible; sometimes all I need is to be interested in one. This may sound noble—and may even be—but it’s also frustrating.

Take the situation I was in a few years ago when I was dating a guy who wasn’t really long-term relationship material. While somewhere, deep inside, I knew he wasn’t long-term relationship material, interest in a man can do something funny to my ability to accurately judge his most glaring red flags, let alone break off involvement with him because of them. It’s not that I can’t see them—it’s just that they become vague or justifiable or at least not relevant.

So I was dating one of those guys when a man I’d long admired began asking me out. I liked him but literally couldn’t see past my then-fixation so I explained that I couldn’t go out with him because of my feelings for the not-really-long-term-relationship-material guy. He expressed his honest opinion that this guy was a waste of my time. “He may be,” I said. “But it’s something I need to find out for myself.” By the time I’d discovered that he was right, the man I’d long admired had started dating someone else—a woman he ended up marrying.

I’m not saying that I should have started sleeping with him or that sleeping with more than one man at a time is a good idea. I’m just saying that the other way sounds like it may be less emotionally painful. I have a friend who’s able to sleep with more than one man at a time. She tells terrific stories, never sounds upset, and I’m always grateful I know her when I get an assignment from Maxim because she can provide me with more sex anecdotes than I know what to do with. But at the same time, I don’t really understand her. The other single women I know get involved with just one—usually one who’s cut from the same cloth as the not-really-long-term-relationship-material one I mentioned. The girl usually desperately wishes she could get herself to sleep with someone else since it would be a good way to get her mind off of that one guy; sometimes she even tries it. But inevitably she reports back that all the experience did was make her long for the guy she’s really interested in. For women, trying to spread the focus always seems to backfire.

And men—well, it’s hard to generalize about these things but I’ll never forget what a male friend of mine from college told me: essentially that if a man could guarantee that it would be kept secret, he would never turn down sex—no matter how committed or in love he was. Now I know that this statement says more about the guy who said it than about men in general but at least part of me believes it’s true.

Perhaps Helen’s friend had it figured out best—minus, arguably, her penchant for sex with old men. To be able to go around and have all that sex without oxytocin or female sexual shame getting in the way is something that I think would actually—dare I say—be liberating for women today.

Don’t believe me? Last time I spoke to that one friend who knew how to have casual sex, she’d fallen in love—with a guy cut from the not-really-long-term-relationship-material cloth. She was tormented and obsessed and sounded, in short, just like other women. I was disappointed—the way some Britney Spears fans may have been when they found out she wasn’t really a virgin. My idea that women could indeed have sex like men because I’d seen her do it was shattered.

Maybe more women like that are out there but I somehow end up only being friends with the one-guy girls. Or maybe Helen was doing some exaggerating. Or maybe, ironically, those footloose and fancy-free girls capable of carrying on simultaneous affairs are less common today than they were in her time. Recent studies are suggesting as much. But is all of this one-man focus really what’s best for single women?

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    • Veronica

      I think it happens more than people think, but we don’t hear about it because women are more subject to social pressure in regards to sex. A man is allowed to boast of his sexual conquests, but a woman will be regarded as a whore for the same behavior. Even if a woman is having awesome sex with various partners, she may choose to hide it because she doesn’t want to be harshly judged by her friends. The real rarity is the woman who is unafraid of judgment and shares her experiences with multiple partners. I wonder if more women like this were open about their sexuality if more women would follow their example.

    • Anthony Mark

      Dear Anna
      Thank you for another super sexy column and for sharing you personal story about losing out on that nice guy
      Your other guy friend is right
      Any man will NOT turn down sex if he knows that he will not get caught
      Excited for the book

    • Axel

      I think is up ned to be really open. N have verry good comunication w then person up wants to doit but is good experience do that my girlfriend talked a about n we did

    • Anthony Mark

      Another sexy column by Anna David
      Thank you for sharing your stories with us
      I am so sorry that nice fellow got away and married someone else

      Your other male friend is right a man will never turn down sex

      excited for the book

    • Marc

      Veronica is correct. Women (some women) are really great at keeping secrets. I was my third girlfriend’s best-kept secret from her boyfriend. I didn’t mind because I was in it for the sex anyway. We didn’t talk about him much except when she’d mention him as an aside. I think for her it was about control, the idea that she didn’t need to depend on one guy to meet her romantic needs made her feel like she had options.

      It didn’t last long, but over the years I have discovered female friends who’ve had side romances to go with their commited lives.

      I make no judgements on this.

    • Ruby

      I find that whenever im interested in someone or in a relationship i notice other men way more than usually would, i think its probably partly about control and a fear of commitment but in other ways its just sort of like a switch goes on? it leads to troublesome relationships.

    • Alison

      I have the exact opposite problem from you (as in the author of this article). Once I sleep with a guy, he becomes invisible to me. No matter how good the sex is, or how much I liked him before we slept together, I lose interest afterward. Not because I’m ashamed of myself or afraid of commitment or rejection or anything like that — I just have a short attention span and get bored easily. So yeah, sleeping around? Not hard for me. Perhaps scientists should study me and see if I’m producing some sort of anti-oxytocin. Women could take it before sex as a vaccine against falling for a not-relationship-material kind of guy.

      • jj

        Alison Rosen!!!!

    • jj

      Wow, its really very sad that there is no mention from Anna in this article about having more partners and getting STDs and passing them on.

      Seems like Anna David is thinking with the same kind of ancient pre-STD rationale that Helen was.

    • Hanna

      Until recently I was very active with multiple partners. Because I wanted to have fun and have new experiences. I liked all those guys but just not that much. If I was with one guy, he was one my mind, as soon as he was out the door, I was free for something else. Yes, I even slept with two different men in one day, simply because I kept them seperate in my head. Took a shower though.
      Now I met someone really great and even though I still see other men and can admire them, I only want the one guy in my bed and my head.
      Just because someone can have sex without commitment doesn’t mean they can’t fall in love, with the wrong guy or the right guy.
      As for STDs, use C-O-N-D-O-M-S. Jesus.

    • juney

      i think its disgusting thats why divorces are up i cant see why you cant be happy with just one person this society is disgusting because today it tells people one night stands are ok and they are not people dont consider stds and have some damn morals you performing sex acts on one person and even if you took a shower performing them on someone else DISGUSTING why dont people find someone that you re interested in and sleep with them only them i think thats the reason we have so many perverts in todays society one question what happens when you decide that you want to be with that one person and they find out about all the people you been sleeping with i ask this because i know of people who their exes has pictures and videos of them having sex what would you say if you found out that your boyfriend or girlfriend was still texting their ex im the type of guy who could be with one woman my whole life and be happy but no ive been cheated on and you know every single time they tried to come back im not trying to force my opinion on anyone im just saying how i feel and just like they call women sluts guys can be sluts too

    • Margaret

      Having sex with more than one man is empowering for a woman. It isn’t about being married and cheating on one’s spouse. Nor is it about taking on the whole football team. It is liberating for a woman; having multiple sexual partners at variant times at her convenience. Is no different from being in a traditional relationship one-on-one where one or both partners feel the need to move on seeking greener pastures at one time or another. Obviously stressing the importance of precautionary aids both for prevention of STDs and/ or birth control is a necessity especially in society today; and it’s also sensible to be aware of the health, historical habits, and preferences of your sexual partner(s).

      The act itself is about pleasure; giving and receiving. The concept is about discreetness, timing, and how much of an emotional entanglement the woman is interested in, as well as strengths and weaknesses. Being feminine, with a ‘tiny hint’ of the mentality of a dominatrix, a spontaneous knack for scheduling, and an active interest in being adventuresome should be encouraged. Women are human and have needs just as men. To accept and enjoy what was freely offered with no one other than one’s own self aware of what was being engaged in or with whom is an ultimate indulgence.

      Each man brings a new venue to the atmosphere of the moment, something different to offer. A man receives his own personal sexual awareness education in a variety of environments, cultures, or adventuresome techniques, which goes along away towards providing gratification in a reciprocal exchange.

      A continued education goes a long way towards a well rounded woman – broadening her horizons. A woman learns what she likes, feels, and wants from a man, the art of playful erotica, as well as, how to communicate her needs. A woman also learns what a man enjoys and how to pleasure him. Obviously this is not for every woman, but it may be considered as having its advantages. If a woman knows her mind and what she wants there is no shame in going after it. It should be soberly stressed however being “tactful” of what is communicated to personal friends should be of utmost importance. Caution should be observed — keeping some secrets to one’s self could be considered beneficial to both parties for the here and now, but also for the future; and goes along ways towards one’s own peace of mind.

    • Amber

      It really depends on the woman, and how she feels about these kind of things. I am with the author – being with a guy gives me blinders as far as potential mates are concerned, I’m a one-man woman and that’s that. But both my sisters have decided that monogamy totally isn’t for them, and give any guy they get interested in the “Look here, I don’t do the boyfriend/girlfriend thing, I will be with other people, you can be with other people, let’s just make sure we keep talking about things and don’t make each other uncomfortable.” I have known other women who will date a lot of men casually until they find one that they like, and others who get a thrill out of cheating on their partners. People are infinitely varied.