Why You Shouldn’t Have Sex With Your Friends – Or Should You?

group of friends enjoying the beach

You saw “When Harry Met Sally…” but have you lived it?  I have. Once had a wicked crush on my best friend from eleventh grade. Lost touch, got back in touch, lost touch again. We hadn’t seen each other in four years when we reconnected after college, but when we did, we slept together. It was everything I’d dreamed of, but it was so…foreign…and somehow, wrong.  We stayed in touch for years afterwards — but we never ever got together again.

The thing about friendship is that you’re dealing with an established commodity. It’s not like meeting a cute stranger, swapping spit, and giving it a whirl. The stakes, in this instance, are a lot higher, because there’s actually something to lose.

It was everything I’d dreamed of, but it was so…foreign…and somehow, wrong.

Now I’m sure you know a couple of longtime friends who got together after a dozen years of dating the wrong people and now they live happily ever after with their three kids in Sheboygan, WI.   It happens and I’m sure it’s close to an ideal situation.  I mean, after all, who better to be your partner than someone who knows you as a friend first? But this is the exception and not the rule. 99% of relationships fail, otherwise you’d be married to your Spin the Bottle boyfriend from sixth grade. So if all relationships are fraught with danger, yet who better to navigate it than a trusted friend, what can we conclude?

Well, we know that sex is complicated. For some, it’s a lustful response to something visual. For others, it’s a tender, wordless expression of affection. Some people have sex. Some people make love. Women also have the added pull of the “cuddling” hormone oxytocin, which bonds them emotionally to men and makes unattached sex even more difficult.

Factor all this into the loaded variables that come with friendship.

Maybe he’s been pining after her for years, playing the dutiful best friend.

Maybe she’s spent all her time dating jerks and never bothered to consider him before.

Maybe they live in different states.

Maybe they work together.

Maybe they’ve never hung out socially before.

Maybe they spend a lot of time together already.

Maybe their relationship is a secret.

Maybe their friends always joked about them but she said no.

Maybe she tries his last name on for size.

Maybe he pictures her naked….

Maybe they’ve talked about it before.

Maybe they just got drunk and kissed.

Maybe she’s ready for the real thing.

Sex with a friend is a minefield of maybes, and a good majority of the time, you don’t make it to the other side without losing a limb.

Maybe he’s not.

Maybe, maybe, maybe.

Sex with a friend is a minefield of maybes, and a good majority of the time, you don’t make it to the other side without losing a limb. That’s why, in my humble opinion, sex with a stranger beats sex with a friend. There’s no baggage. No white elephant in the room. It’s far easier to let it all hang out if you know you may very well not see your sex partner again. With your friend, you have no choice. It’s your friend.

You know how much the friendship’s worth to you, and what you stand to lose by letting sex get involved. Personally, I think it’s a gamble that can pay the hugest possible dividends. Just remember that in the end, most gamblers lose.

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  1. 1

    Great example, I did at one time live in Sheboygan, I never knew people outside of Wisconsin knew about the place. I do very much agree that without a good foundation, one cannot build a good future. Sex, Puppy Love, and the other attractants that draw to people together do fade, and it is one’s ability to spend “down” time together successfully that can make or break relationships in my honest opinion. Evan, I think most of your readers know things like this, but like me “Skim” over these obvious lessons, and it takes someone like you to remind us of them and how to apply them to our decision making.

  2. 2

    I must say that I have a friend whom is very close to me; we have always hung out and had a great time just enjoying our friendship. Now, we do have sex when we feel like it. We both know that there is no attachment; we both know we aren’t the other’s only partner; we also sometimes bring our “buddies” to join. Sometimes we talk and cuddle afterwards; but it is just as likely that one of us tells the other to be quiet, give them room to sprawl out, and let that person enjoy happy time after an orgasm (though usually the latter causes a bit of laughter). We also can kick the other out of our house if we so desire and our feelings aren’t hurt. I think you just need to have COMPLETE honesty and KNOW that you would never be able to date the other person. These two things are VERY hard to find in one person, perhaps it was just a stroke of luck, perhaps it is that we are both bi and know that neither one of us could be tied down with one gender; maybe, it was his experience at handling this type of situation. It might also be that we are still relatively young and in college; I am 22 and he is 29. It might also be that neither one of us has any desire to settle down. All I do know that for him and me, it works. I just want to say that it does happen.

  3. 3

    I thought that I should also mention that it has been working for over a year… Some classmates had happened to hear a conversation that him and I were having and remarked that our friendship would turn sour in a week if we would actually have sex. To which of course we had both laughed. It also doesn’t bother me if he doesn’t want to hang out or breaks plans with me because he is with someone else; even another female. I get it; I have been there. Sometimes, you just want someone different; people are very different in the way they generally like to have sex and sometimes you just want a change. I was just reminded of those points and had wanted to clarify.

  4. 4

    My name is Morgan. And I sometimes have sex with my best guy friend, who’s been my best friend for over a year. Nothing’s awkward. & we both know there’s nothing more behind it. It’s just friendly-sex. Period. And neither of us have feelings for the other one, so it’s pretty easy.

    1. 4.1

      I have been friends with this guy for almost a year,the first time we meet we made it clear that we both have partners,it felt different being with him the way we have fun I coulddnt resist him and we slept together we always do wen w meet but I sometimes feel somehow cz I feel like I am getting attached to help him and would talk about and say we shoulddnt end up at that stage coz we woulddnt want to hurt each other I don’t want to loose him as a friend,even though I sometimes wish we could dyt but still I feel safe and fine having sex with him

  5. 5

    As a woman, for safety reasons, I’d take sex with a friend over sex with a stranger anytime. As a sole provider, I owe it to my family that, when I get intimate with someone, it’s with a safe enough person that I won’t turn up in a garbage container the morning after. I know, gross exaggeration, but you get the general idea. Works so far. Hasn’t ruined any friendships as yet.

  6. 6

    Wish my bestfriend was my girlfriend. But idk how to get her. She said I’m like a brother to her and Ive liked her b4 I even hit puberty.   Now I’m 15 and she’s seventeen and I’m afraid to wait any longer cause she said she’s been looking at other guys which really pisses me of. Because of how long I have wanted her

    1. 6.1
      Karl R


      Since you’re 15, you haven’t learned how to translate what women say into what they actually mean.   When a woman says, “You’re like a brother to me,” she means, “I’m not sexually attracted to you.”

      Find a different girl who is interested in you.   (And take precautions.   You’re a teenager.   You don’t want to screw up your life before you reach adulthood.)

  7. 7

    I been having sex with my friend for 5 yrs we always had a thing that we did when we did it he pretended to be slp but he has a new guy now and he text me and told me its over we cant do it anymore my advice dnt have sex with yur bestfriend becuse at the end of tbe day yu cant be angry unless yu had feelings from the start and thats wat sucks about it i learned the hard way

  8. 8

    Real friendship IS love.   That’s why FWB is, to my mind, not friendship at all.   It is egoism at its very worst.   Admittedly with agreement.   Ha! But that’s where it gets screwed up.
    If you truly are friends, you maybe are hoping something comes out of it.   It might, but I doubt it.   Otherwise……you’d be a couple.

    1. 8.1

      I would have thought similarly when I was younger, but currently I am in my mid 20s, and for many reasons prefer my close friendships to relationships.   I have found a really happy balance of being FWBs with several close friends, where there are feelings for eachother, but no jealousy and drama.   It’s great, we are all able to communicate well, respect and care for each other and have our freedom- i’d say there are less problems then i’ve had in relationships where desires and needs often have to be edited and feelings really get hurt..    it’s all in what people are comfortable with but I’m starting to see that this can work great with the right people.

  9. 9

    I ‘HAD’ a best friend, a soul mate. We were friends since we were in our preteens. Of course we moved on with our lives, I got married had children, he moved to the east coast and got married had children. He was stationed in Afghanistan in 07. I emailed him to tell him how proud I was of him and I prayed he’d be safe. He responded and a few back and forth notes later, he told me of how much he had a crush on me and still did. It sparked a fire in me and I too wondered how that would be. But didn’t have the same feelings I guess he did. I made it perfectly clear I wanted the friendship more than anything else in the world. I loved him like a sibling. He continued to mention his crush and thoughts regarding it. Later I was notified his wife had found his letters. She was very upset and should have been. He lied though… He told her it was me, a complete opposite scenario. I was devastated. I understood his reasons. However I was floored. His family, his brother all I was very close to. Now, nothing. He made me feel as though I had caused this. Someone who I would have trusted my children with, my life! Now, I often find myself upset and wishing I had that friend back again. I know deep inside it will never happen. I know he probably never held the friendship in such high regard as I. It kills me to know I was taken as a fool. I do still love him, love him deeper than any friend I have ever had. I don’t love him in a sexual way, yet a way that is far greater, a kindred spirit kinda love. I am broken hearted and even after several years I MISS HIM DEARLY.

  10. 10

    I’m talking to this guy we have been friends for 3 months I’m 20 and he is 21. We consider ourselves friends with benefits. I have a bf. And he knows it it’s fine with him. We talk to each other about everything! The sex is great I don’t think there is anything wrong with having sex with your friend. We are just friends having sex no strings attached. No feelings are involved because we both belong to someone else. But damn. The sex is amazing I can tell him stuff that I wouldn’t tell my boyfriend

  11. 11

    SEX IS ONLY WHEN YOU’RE MARRIED! You shouldn’t be screwing anyone other than your spouse! Single people need to wake up and realize sex is for married couples !

    1. 11.1
      Grounded and Happy

      Shawn, your “friend” was no friend at all. His behavior clearly shows that. A friend would never throw you under the bus like he did.

      Consider yourself lucky to have seen his true nature before the pain it caused was even worse than what you experienced. Him being out of your life is a blessing. I hope you will realize that, instead of losing something, you gained a life in which you no longer have  pure hearted faith  in a person who didn’t deserve it at all.

    2. 11.2
      Grounded and Happy

      Mandy, some spouses don’t want to have sex, while their mates do. Some married couples don’t even like each other. On the other hand, some unmarried couples are true friends and partners who enjoy a vibrant sex life. This, of course, is true of some married couples too.

      My point is that inflexible rules like “sex is only for married couples” ignore the fact that there are all types of working relationships. Just because, for you, sex must come with marriage, holding to that position doesn’t gaurantee a happy marriage. And, to me, what’s the point of being married or in any romantic relationship if you don’t enjoy it?

  12. 12

    This article is ridiculous. I only have sex with my friends and it’s just us having some fun together. I’d much rather have sex with someone I trust and know and feel comfortable with than a stranger that I want to leave my bed when I’m done. Sometimes it’s just better to get sexual tension out of the way.

  13. 13

    I hooked up with an old friend who was in open relationships. I am monogamous, myself and considered it just a casual fling.  However, for me, I am not emotionally able to be intimate with a partner without having feelings. I cannot wrap my head around the open relationship thing. At the time, I was just out of a long term abusive relationship and it had been a very difficult breakup. When my friend and i became intimate, one of the other ladies he was seeing got jealous, pitched a bitch and broke up with him – even though she had other partners, too.  I happen to respect and adore this guy and posed monogamy to him. He accepted. I trusted him because I had known him for so long. He was and still is my dear friend. We have been exclusive for five months. I grapple with severe insecurity issues and our mutual friends are very critical of our relationship, so I can’t say it’s not rocky. Dating him is like dating a coworker, in that everybody knows our business, everybody has an opinion and everybody thinks they’re more right than i am in judging his commitment and sincerity. After five months, not one of those ladies has come forward to apologize for their discouraging judgements. Also, because he had a reputation as being available, several other ladies find it normal to try to entice him into liasons again, exacerbating my insecurities. So, the jury’s still out on the success or failure of my circumstance. So far so good except for my intense insecurity. And if it fails, it won’t be because our jealous friends predicted it. As far as I’m concerned, it has been well worth it for the possibility of having a partner who I admire and adore. If it doesn’t work out, I hope I can be mature and emotionally stable enough to love him platonically again. Time will tell.

  14. 14

    I have   been friends with j for 10yrs, since we were 17.. he was a very close friend for many years and my partner’s (now ex p) best m8 be was akin to a brother to me or a cuzin, lived with us whn he had nowhere to go no job ect. After a few years He also got a partner, “tee” t was/is not a very nice person and as his famz we nvr liked the way she treated him but we accepted she was with him … he’s   a bigger guy and has quite low self esteem, he was with her for 5yrs they have 3kids together. Me and j have stayed in touch casualy even whn my ex partner and me split, I drove j to his back operation surgery cuz he had no support. J auctualy told me he found my (ex)partner and t writing lovely letters to each other!! (My ex is in jail)   j always looks out for me he’s my brother from anither mother.We’re both alone now, no partners or kids in our care .. and he brings up hes always hada crush on me!! He’s   been   aakkinng wat itl take or cost   for 1 time… He’s agreed to give me gold and diamond earings for one occasion… he swears nothing will change.. which I keep saying is the reason BUT I seriously am SO NOT attracted to him AT ALL I realy canot picture it…. Ii will feel so yuk .. he’s   been going on for months and months now… I feel kinda mean I keep saying noway but I really DO NOT want to fuk my friend

  15. 15

    Hmmm. Sex with a stranger? I swear nobody cares about diseases … and some that can stick with you for life or even kill you. Ok, um, no.

  16. 16

    Why would you screw a stranger you have no idea where they’ve been! Not to mention the consequences of birth control failing.

  17. 17

    **Poster Notice**
    To whom it may concern,
    At this time, I find it best to express, I have always been a firm believer men and women cannot “be just friends”. Perhaps and please do, feel free to judge me (voiced negative when digested correctly, can add to one’s strength of character) so, no judgement, (on my part) of your voiced opinons of me! We our all that much more brave hidden behind our computer screen masks, firing typed words on a keybroad like bullets.
    It is, at this point, now that I would like to share my experience on the topic. Perphaps it was a lack of affection, perpaps it steamed from a want to share love, but whatever sex my friends have been. I a women, have never held myself back from the idea of more intimate moments. But please, keep in mind “sex”in the vaginal, penis term way of putting was never what was the goal. There is a secret pleasure, a gift even, and for only those involed.
    **Complications arise, in the forms of worry, perphaps of from the act itself. But rather the reporcussions… We didn’t do our all (like have “safe sex”) and now our loved one is a risk i.e; didn’t use a condom, for many unaware it is recommended, even for women (while giving them head to also, use a condom)**
    Life, is taking chances, “We are damned if we do, and damned if don’t  ” Whatever, choice one makes leave us one to any number of possibilties, take the bad with the good. For one cannot live without the other.  ” Life is either a great adventure or nothing  ”  -Helene Keller
      “The greatest mistake is the one from which you learn nothing  ” -John Powell

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