The Editors Debate: Should You Sleep With Someone On the First Date?

The editors think “sleeping with someone” means snuggling really hard for the whole night and loving each other. That’s how babies get made.

Fooled you!

Jennifer: I think many women have a notion that not sleeping with a man on the first date will cause him to stick around. In my experience – and through talking to my male friends – men don’t ditch you because you sleep with them on the first date, men ditch you because you’re the kind of girl who is obsessively focused on how to make a man stick around. It’s not so much the sleeping with as it is the squealing like a lobotomized schoolgirl – even if only in your head – about how he’s OMG THE ONE – when you’ve known him a total of 7 hours. If you go about your life afterwards without focusing on him too much, being polite and somewhat available, but also willing to walk away at any second if you’re not getting what you want out the relationship, well, it’s been my experience that men are MUCH more likely to stick with you.

Ashley:  Am I supposed to argue as if I disagree here? Like: Fuck you, Jennifer. Clearly, if you do things that bottom-feeding women’s magazines say and memorize the countless tips and are the sort of person preoccupied with “snagging” a “guy,” you are going to attract really great men who are thoughtful and interesting and driven and talented. And they’re going to want to wife you!

Jennifer: Oh no! The editors agree!

Ashley: I don ‘t like the cut of your jib.

Jennifer: I think women who believe that not sleeping with a man on a first date ensures that he will love you are simple minded morons. Men’s interest has little to do wth sex unless sex is the only thing you have to offer. I think.

Ashley: We need to find a way to argue with each other about this.

Jennifer: Oh, phooey. No, I’ll just type more words.There is a wonderful quotation in Peter Pan, of all places!

[Mrs. Darling] was a lovely lady, with a romantic mind and such a sweet mocking mouth. Her romantic mind was like the tiny boxes, one within the other, that come from the puzzling East, however many you discover there is always one more; and her sweet mocking mouth had one kiss on it that Wendy could never get, though there is was, perfectly conspicuous in the right-hand corner… [Mr. Darling] got all of her, except the innermost box and the kiss. He never knew about the box, and in time he gave up trying for the kiss. Wendy thought Napoleon could have got it, but I can picture him trying, and then going off in a passion, slamming the door.

Ashley: Peter Pan is so weirdly erotic.

Jennifer: I know. I think there’s something to that, though. That idea of keeping something for yourself. Always have some innermost kiss that no one ever quite gets. It’s the quality of something elusive that makes women interesting, not just when they will or won’t spread their legs.

Ashley: If someone tried to initiate sex on a first date with me, I would not go on a second.

Jennifer: Really?

Ashley: Yeah, that’s not my scene. I mean, I wouldn’t be pissed about it. And this isn’t a moral judgment of any kind.

Jennifer: I’d be offended, probably – unless it was a man I desperately wanted to sleep with. And then I would be too busy to be offended, because I’d be having sex. But that’s happened hardly ever.

Ashley: I’m too private. Sex with strangers has absolutely no appeal and it takes a long time for someone not to be a stranger. So someone who wants to have sex on the first date is, in all likelihood, fundamentally incompatible with me.

Jennifer: I generally feel the same way. The times – fine, time – that I have deviated from that are times when there had been a history beforehand.

Ashley: Which is consistent with what you’re saying.

Jennifer: But if you see a man, and want to sleep with him on the first date, heavens, why not? Just be able to be comfortable never seeing him again. Always, on some level, even if you’ve been with someone for years, be aware that you might never see them again and feel that while you’d be sad life would still go on, and you would be okay, because you’d still be you. I think the real risk of first date sex is just that it might make YOU more emotionally attached. Basically, if it’s going to make you go all bunny boiler, know that’s not a good decision for you. So hold off. Fair? If you’re capable of enjoying it and feeling that if you never see him again you will always think of him fondly, well, how wonderful! By all means! Sex away! Look, on a first date, I’m not standing in the bathroom thinking “omg, I hope he grabs my boob!” That line of thinking is hilarious and insane to me. I’d be trying to figure out if I even liked him. Judging. I’d be sitting there judging. I love that stuff.

Ashley: This is boring. Why are you so oppressed by the patriarchy?

Jennifer: BUT I’M NOT. This entire conversation has been presented by my smooth European alter-ego, Ellen Olenska. Ellen fucks when she feels like it, then tosses them cab fare. She keeps her high heels on the entire time. Ellen loves danger for other people in the sack.

Ashley: I’m terrified of you.

Jennifer: If I opened m mouth to speak now, you would see that my accent has become Romanian. I mean, dude, that thing about “be aware that one day you’ll die alone?” I don’t know if I actually do that, in practice. Even though intellectually I’m very aware of that. I think there are times I’ve taken that intermost kiss, stuck it in the innermost box, wrapped it with some Easter Egg printed paper and presented it to people.

Ashley: Your labia are typing this, aren’t they? I’m never going to sleep again. You know I have a sleep disorder. This is terrible.

Jennifer: I’m clutching a high heel in my labia. Sorry, Ellen Olenska is.

Ashley: LIKE THE SARLACC! Oh my god. I’m never sleeping again. Boba Fett is trapped inside of you. Is this how I lost my keys? My sunglasses? WHERE DID MY SHOE GO?

Jennifer: Ellen “ate” them.

Ashley: At least this explains why those sides of beef and turkey drumsticks keep disappearing from the office refrigerator. I can find some solace in that.

Jennifer: Okay, but there’s a point that there’s probably some difference here between what we know is true and the way we actually behave. While I do believe in maintaining, always, some emotional distance for your own benefit as well as the fact that it will make you more attractive to others, there have been men whose facebook profiles I have checked like 5 times a day. That’s not very “even Napoleon couldn’t get that kiss!”

Ashley: Well, I’m completely consistent. But yes, you have all this WASPY affectation about intellectual distance and stunted emotional development and blah blah blah Valium blah blah blah, but in practice, your giant disembodied vagina is snail-sliming around the office right now, frothing with much indolence atop the water cooler and beating its lips like some kind of fleshy pink Mothra.

Jennifer: You understand me. The innermost kiss – it’s yours Ashley! It’s always been for you!

Ashley: I will be the Boba Fett in your vaginal sarlacc pit, gestating there, adoring you from within.

Jennifer: I will shut you out afterwards to keep you wanting more. You won’t hear from me for like a week. I will not return any of your texts. Then on Friday I’ll be like “dinner? Half an hour? The Four Seasons?” You will drop whatever you are doing and run.

Ashley: Do you want a foot rub?

Jennifer: You know the heels stay on.

Ashley: My hands and heart, they bleed for you.

Share This Post:
    • Chris Wren

      Your sentences hurt my brain… in a good way.

    • Peyton Banks

      Age of Innocence reference!! Huzzah!

    • Eileen

      I stopped reading once Jen revealed her alter ego is Ellen Olenska. Because we already know how I feel about the collected works of Edith Wharton.

      But in my (admittedly limited – I’m just one girl!) experience, unless you were already good friends, sex on the first date usually doesn’t end in anything more.

    • Aisleen

      I have literally NO experience with this – I’m not kidding when I say (type?) that I’m a nineteen year old with little more experience than innocent pecks among some not so innocent classmates’ lips – but this issue has always fascinated me (every time someone asks me to contact them, be it for a job or otherwise, I always joke about having to wait three days to call; my best friend and I didn’t go out to dinner together until the third time we hung out in public, etc). I think, in general, the rule of threes is really foolish, but as a lot of friends of mine are sexually active and feel like coming to the girl with no experience on sex for advice is a good idea, I also think that sometimes it’s going to take three dates – or more – to feel like you’re emotionally ready to partake in intercourse. I think it depends on the woman, first and foremost – some find sex to be a strictly physical act, some find it to be highly emotional, some are a balance – and I think whether or not it’s appropriate for a woman to have sex with someone on the first date is based a lot on that. It’s also about the man, how comfortable she feels around him and whether or not he makes her FEEL like having sex the first time they meet. If she feels safe and they’re safe during, then, yeah, go wild on the first date. If it doesn’t feel right, then don’t do it. It seems so simple, but it somehow always ends up becoming difficult.

    • Paige V.I.

      this is the reason i love randomly looming over your work space…

    • Qixaoxiyyy


    • Allie

      This might be a little misanthropic of me, but sometimes you need to wait to have sex with a guy just so they see you as a real person, instead of moving right along with the objectification. I don’t care about “hanging on to a man” because that’s like, tricking them into liking me. But it gets a little tiring to have someone you actually got along with keep (unsuccessfully) booty calling you for months after you tell them you’re “not looking for the same thing” because all they were interested in was hooking up.

    • Elle

      90% of men will just take a one night stand and run, its horrible even if you were ‘friends’ it will still occur. There are many nice guys around, my ex and I are friends we were just not suited for each other, he still comes round and we chat about our families and whats going on in our lives, in many ways he is a better friend that boyfriend but getting bank on track you never know what kind of man the guy you are dating really is no matter how long you have known them. Its a cynical look at first dates but my friends have had the exact same experiences. Gentlemen are few and far between in this day and age.

    • kjhyugtfr ijuhygtfr

      I will STOP seeing you because there is something wrong or dysfunctional about your personality.

      It will have NOTHING to do with when you have sex.

      In fact, if I ask for sex, and you reject me, you can pretty much GUARANTEE that I will NEVER call or ask again!

      “Wait, you want to go out on another date, that’s why you called me? Well, last week you didn’t seem at all interested in any sort of relationship, or even just sex. So, why would you be asking me to spend more time with you? If I am going to invest my time on someone, wouldn’t it make more sense to do it with some girl who has a future here? I really don’t see the point of another date. So, I’m going to have to pass on your offer. But, thanks anyway!”

      There is only ONE way to reject me sexually, and still keep things going.

      “Yes, I want to have sex with you, actually pretty much. But, I just need time, to feel more comfortable together. That’s just the way that I am. I have to feel in the mood, and I need to feel comfortable, in order to be sexual with a new man. And, while there is attraction here, I’m just not at that point yet.”

      That is the ONLY way to not have sex, and still remain with me.

      Otherwise, a sexual rejection is the END of you, automatically, and forever!

      There are simply too many other attractive women who do want to have sex for me to waste time with a woman who does not.

      There is no perfect ONE, that is meant to be my mate. I can build a life with a million different women and be perfectly happy with any one of them. So, if you are not interested, I will move on, and find another who is!

    • Papa Geek

      “I will be the Boba Fett in your vaginal sarlacc pit”

      People are going to wonder why I’m doubled over laughing in my cube right now!!

    • Louise

      I don’t know why everybody’s so worked up about this topic.

      I went on a blind date for the first time ever a week ago, and people told me (especially my mom) that it was utterly slutty to have sex the first and second date.

      Call me slutty, but things developed into romantic cudling in bed, and before any of us really thought about it, it had been done…

      And now, I am the happy owner of a very sweet boyfriend who just called me his “only one”.

      Not all men are horny pigs. Sometimes, the best way to get a man is to show him utter trust and enthusiasm already from the start. (but you should only do it if it feels natural to both of you, and not forced)

    • Louise

      Oh, and a note:

      Give it a try. If you like each other, you should not try and restrain your desires. Sex might be one of the best ways to show him that you are interested in him. Only have sex if you truly are interested in getting a reltaionship with him, otherwise he will just be fooled.

      However, if you don’t have sex with him on the first date, and he quits, then perhaps he was not worth it? (lack of understanding for women’s feelings and thoughts).