Thoughts on Hooking Up with a Taken Man

I entered my friend’s apartment in a giddy state, excited to see quite a few people from our writing workshops who I had been eager to interact with—artists I admired from afar but never had the courage to praise, people whose personalities pulled me in but I felt too awkward to approach—and figured now was the time to go for it. Among these was Keith, a young poet who ran a literary journal, and his long-term girlfriend Elizabeth, a slender and graceful woman working on a masters in literature. Practically inseparable, always holding hands or sneaking affectionate glances, they were the kind of couple people saw and thought, “love does exist and it looks as adorable as I imagined.”

I had chatted with them now and then, but never had the chance to progress beyond small talk. I was surprised to see that Keith had come alone to the party; Elizabeth had went back to campus for the weekend to work on her thesis with her advisor. As it turned out, Keith and I had quite a bit in common and spent a considerable portion of the night forming a friendship. We were perhaps a little too friendly due to a steady flow of alcohol, but I wouldn’t have called it flirting. Coming from a family with divorced parents (due to my father’s multiple affairs), and having seen the damage that does to a person, I’m careful not to make advances on taken individuals.

Eventually a group ended up in a circle, passing a wine bottle around, talking about our sexcapades. Keith expressed his enthusiasm for giving road head, and until that moment I hadn’t known eating a woman out while she drove was possible. Impressed, I commented that if he and Elizabeth ever broke up he should give me a call. I realized it was inappropriate as soon as I said it (though admittedly I would have responded similarly if someone said they make awesome chocolate cakes—of course I’d want to try). I apologized for the comment, feeling guilty for overstepping boundaries and disrespecting his relationship, but he told me not to worry about it.

Around 3:30am, after several glasses of wine, two joints, and some champagne, I whispered to a friend that I needed to lay down. She followed me into the bedroom, as did Keith and some other curious people, and soon five of us were cuddling in bed. Keith got into bed next to me, positioned so that I spooned him. I found nothing explicitly wrong with this: with five adults in a small bed, cuddling was necessary to fit. But when everyone else got up to roll a joint in the next room we lingered, staring awkwardly at the ceiling and ignoring the heavy sexual tension. He asked if I had ever felt a connection with someone. Careful with my words, I rambled into a new conversation, but he steered back. He said he would happily spoon me but thought it’d be rude since he couldn’t without getting hard. I brushed it off, saying I had a friend I casually cuddled with who sometimes got a boner and it wasn’t a big deal. I should’ve just confronted him about his flirting and said, “you have a girlfriend, I am interested in you, but this is not okay,” but it didn’t occur to me at the time. I guess I assumed if I avoided his advances he wouldn’t have the nerve to try anything. And of course part of me wanted him to keep trying.

We joined the others to smoke and then crawled back into bed. He slipped his arms around me and I snuggled into the curve of his body, knowing we had crossed the threshold. Everyone mumbled and giggled for a while, speech slurring in and out of sleep. I too had drifted off—or rather, I had entered an exhausted and drug-influenced light sleep—when I felt someone touch me between my legs: tentative and invitatory. I froze, flashing back to when I was sexually assaulted in my sleep at college. The same hazy thoughts came back: acknowledging the pleasure and then the stomach-dropping sickness after realizing I was being touched without my consent.

I knew it was Keith. Was I offended that he assumed he could touch me? Did he intend this in a creepy way? Perhaps he assumed I was still awake and had slid his hand slowly over my thigh, waiting for my reaction? I stopped his hand, taking it in my own while I leveled my breathing. Unlike the time in college, I was attracted to Keith and we had been somewhat intimate leading up to his attempt. However, I don’t think anyone should just grope someone and assume they will be okay with it. Even though we had flirted and cuddled before didn’t automatically mean I wanted something sexual with him. But for me, in this particular situation, I did want it.

After calming down from the flashback, my (kinky) sexual side tuned in, and the thought of getting fingered in a bed with three other people turned me on. For a half hour or so we laid there, caressing, limbs intertwining, noses almost touching. He decided to try again, and this time I let him slip down into my underwear. He brushed past my clit and I sighed, which made him smile, a reaction that both adorable and sexy. He went inside of me and I weaved my fingers through his hair, tugging slightly. As far as my experience with hook-ups went, guys usually placed my hand on them, or attempted to jump right into sex. Having someone reach out to me, touching me in ways that made me feel good without any kind of expectation for repayment, felt wonderful. I didn’t have to react or impress, I could just enjoy.

Slowly the room brightened and the others started stirring. Even after people woke up he kept his hand on me underneath the covers. But once we got dressed everything turned back to normal. I’m positive no one guessed a thing as we walked down the streets and got the first train home.

The ambiguity, though quite sexy in the darkness, made my mind whirl in the daytime: did he think I was “the type of girl” who would enjoy being sexually solicited like that? Am I? What does that even mean? Did he see me as the perfect person to cheat on his girlfriend with? Does that mean I’m not the type of person people see as relationship material? Do I even want a relationship? Was I being self-destructive by going along with it? Does what Keith did invalidate his relationship? Does it make his feelings towards her less real?

When I confronted him about the encounter later via Facebook, he said that it had been a dreamlike, intense encounter that had surprised him—both thinking of doing something like it and actually acting upon it. Esther Perel, a therapist and “sexual healer” describes exactly this sentiment in her article about cheating: “…an affair is such an erotic experience [because] it’s not about sex, it’s about desire, about attention, about reconnecting with parts of oneself you lost or you never knew existed. It’s about longing and loss…”

I don’t condone infidelity, but I don’t think Keith meant to be intentionally hurtful with what he did. I’m positive he still loves his girlfriend. I believe that he never thought he would do something like that. I think he felt some sexual attraction towards me and, since we were in a “safe” environment (squished in a crowded bed), he went for it knowing the encounter couldn’t progress even if we wanted it to.

It occurred to me afterwards that I might be what some people label a “slut” or a “whore.” I tend to hook up, one way or another, with someone new about every two weeks. In this particular instance, I didn’t provoke the encounter. I didn’t intentionally seek it out, even if I was wrong to give in. It amuses me that I could fit into the realm of such a judgmental and hateful slur. I certainly don’t feel like a bad or vindictive person. I do feel uncomfortable that he maybe lied to his girlfriend and that I would’ve been involved in that lie, but I don’t feel responsible for his infidelity. To label someone as a “slut” ignores the fact that she is a complex being with a lot of hormones, psychology, and emotions and judges us based off of a single aspect of our lives. The reality is, no one and no situation is that one-dimensional.


I’m curious – do you think it’s possible for someone to cheat and still love their significant other? Are Keith and I both responsible for what happened? Or he is more the guilty party since he betrayed his own relationship? Or, do you think humans are fallible creatures and everyone should cut us some slack? Leave me your thoughts in the comments, or feel free to share you own (‘morally ambiguous’) hook up story.

32 thoughts on “Thoughts on Hooking Up with a Taken Man

  1. I think we’re capable of loving and desiring more than one person. A lot of the prohibition is cultural rather than anything innate. It’s the retrospective search for a guilty party or meaning after the fact that causes harm. We all desire and sometimes acting on it isn’t the worst of all possible worlds. I really enjoyed your writing.


    • I agree. People spend a lot of time misinterpreting other people’s actions and taking them personally (i.e., “they’re interested in that woman which means I’m not good enough” … when really they just happen to find more than one person attractive). Many people have successful polyamorous or open relationships and that’s because no lying is involved. In my opinion, it’s the deceit that hurts relationships, not the affairs. The breaking of promises. I think it’s irrational to assume one person can fulfill everything we need out of life – emotionally, sexually, intellectually – and it’s just as silly to be offended that we don’t fulfill someone else’s every need or want.

      Liked by 1 person

      • We are polymorphous in so many ways but I think it’s more cultural prohibitions than anything internal. Have you read Sex At Dawn by Chris Ryan?


    • I’ve been struggling with that thought lately – is morality subjective or objective? And although I never believed so before, I’m coming around to the idea that nothing is inherently “good” or “bad”, it just is, and humans impose their opinions on it.


      • But if we accept that morality is subjective, we pretty much allow ourselves to be dicks whenever we feel like it, right? Does this mean I can go and nick my friend’s cupcake? If she’s pissed off, I’ll just calmly inform her that I don’t share her interpretation of the situation.


      • What I mean by that is there actually isn’t anything inherently wrong, ingrained in the universe, with you stealing your friend’s cupcake.

        I don’t think anyone should digress, start becoming a dick even though they once believed stealing was wrong. But there are some people who honestly don’t think doing that would be wrong. And who’s to say it is?

        I do think everyone should live by some moral code. For me that’s pretty simple: don’t steal, don’t kill (and all the subcategories of those).


      • Fair enough. Yeah, you’re right – good and bad are abstracts, but we still need them. I think that a good rule to live by is to just try not to do anything that would hurt someone else.


      • Morality is subjective of course. The universe does not label things as right or wrong. We could drawn into a huge philosophical discussion about it.,,,
        but i’m sure that we could agree that society at some level has to have basic shared norms (ie: don’t kill either other, don’t steal..)
        Shaming of someone for sleeping around/cheating is a reflection of a societal norm. Should we accept that norm, or move to change it is the question we as individuals and more broadly as a society needs to address…and do address as we can see happening here right now…

        Slut shaming as a prime example:


  2. I have been cheated on in every one of my ‘serious’ relationships. I used to think it was my fault – how could I not? Was I not appealing enough? Am I not fulfilling something that my partner desires and she therefore looks for it somewhere else? I had no clue. I’ve since come to learn that cheating doesn’t necessarily negate one’s feelings towards your partner. Cheating can just be in the moment. Fueled by alcohol and other substances, one’s base desires come to the forefront and all you think of is getting off. I don’t condone cheating, but I also know that a person can still love their partner before and after.


    • I also believe that anything one does is a reflection of *them*, and says nothing about anyone else involved in the situation. If someone cheats on you, that says something about where they are in their life/mental stability/confidence/etc, not where you are in yours. It’s a process, but I’m learning to not take anything personally any more, neither good or bad things. I appreciate the good and try to understand the bad. I think we’re all just stumbling around lost, trying to figure out where we want to be.


  3. So, I’ve only just found your blog, and have only read this post (so far), but the tagline ‘aiming to end shaming one entry at a time’ is something I massively support.

    I don’t support what you did though. That’s not because I think you acted in a ‘slutty’ way (I mean, what is that anyway? Enjoying sex?). It’s because I think that in this crazy world, we’re all responsible for each other, and by doing what you did, I kind of think you screwed that guy’s girlfriend over.

    So he’s obviously a massive dick (‘Oooh, I think we have a connection’ – yeah, mate, and you have a girlfriend). And he is 50% responsible for what happened. You get the other 50%. Because sure, you weren’t in a relationship with his girlfriend, but you knew she existed (you’ve even met her), and you knew that by being intimate with her boyfriend, you would be participating in something that could potentially cause her a great deal of pain.

    There’s nothing wrong with (consensual) sex per se. There’s nothing wrong with polygamy per se. Neither of these in themselves should make anyone feel guilty or ashamed. But when there’s a party involved who might get hurt, that’s when it gets messed up.

    We all get drunk. We all get stoned. We all get horny. But no matter how drunk, stoned or horny you are, you still know what’s right and what’s wrong. You still understand how your actions might affect others. Let’s look out for each other a bit more. I think a small but significant part of feminism (and just being a compassionate person in general) is not sleeping with each other’s boyfriends. Being fingered is nice. Being decent to your fellow woman is nicer.

    Anyway, that’s my opinion. But I also think that everyone makes mistakes, and what you did doesn’t make you a bad person. Just someone who had a brief lapse of judgment (in my view). God knows, I’ve had a number of those in my time. Good writing, by the way.


    • I suppose that’s why I decided to write this post – so often we hear about cheating from the person who was heart broken, and as result we are less sympathetic towards the people involved. But they’re not monsters looking to ruin someone’s life. They may be lost, confused, insecure, or have a momentary lapse of judgement. Which is part of the reason shaming upsets me so much. No one is the sum of their mistakes, no one is wholly evil. We both fucked up in this situation, and I do feel badly about it. But I would hope people could read this and see that I am an otherwise ‘normal’ person with legitimate emotions, that people who make these sorts of mistakes aren’t sex-crazed inconsiderate sluts or manwhores, if you know what I mean.


      • Yeah, totally. I mean, you just seem like a normal person. I think it’s really important to talk about people as human beings, each with their own complicated psychology, each with agency. That’s instead of throwing around pointless harmful labels like ‘slut’, and drawing a line between men and women and their respective behaviour. And quite apart from discussions of shaming and anti-feminism, sex is a goddamn minefield, and the politics/etiquette of it need to be debated out in the open.


      • Most date rapists don’t set out to ruin someone’s life or intend to commit a terrible crime. But they have not got the right conscience and boundaries so we don’t cut them slack, nor should we. It doesn’t make them “good people who made a mistake”.


      • Actually, most date rapists *do* set out to commit the crime, But I’m sure they aren’t thinking of it in terms of ruining someone’s life, they’re thinking of personal gratification.

        I don’t think we should ‘cut them slack’ in the sense of forgiving them and letting them continue on with life. But every human deserves some kind of sympathy. Rapists, just like any other criminal, doesn’t deserve to be thrown in a jail where the likelihood of them improving is slim. I think if we turned instead to a rehabilitation system we could help these people get their lives back on track and when they’re reintroduced into society they have a smaller chance of committing the same crimes.


      • I just feel like criminals should be treated with the same respect and kindness as we would like them to have for others. People learn by example.

        As for date rapists setting out to commit crimes from the start, that is proven to be true. Rape is most often a premeditated act of violence.

        Check out this article for a few examples:


      • Like I already said. But hey you keep arguing if you want. Cheaters who are unremorseful are just like rapists, I haven’t seen you combat that. We can disagree about whether justice or mercy is appropriate. I say justice. And I’m no vigilante, quite the contrary.


      • You are like Khaleesi =)

        I’m not sure if rapists can be compared to cheaters … one is a violent infringement on someone’s body and rights and the other is disrespectful in a more abstract sort of way.


      • It’s not at all abstract. And it’s violent and the lifetime aftermath is totally physical. You can put your head in the sand about that. It can’t be pleasant thinking of yourself as a rapist.


      • I’ve read that sociopaths can be charming for that reason in that they don’t register a fear of consequences or suffer guilt. I look at it in terms of being your own witness in terms of how you interact with people, that detachment isn’t removed but a measure of control over yourself. I’ve never met a sociopath, narcissists definitely but not a sociopath or a psychopath.


      • That’s the fascinating thing. Usually you can’t tell, in Kevin Dutton’s book Flipnosis he says that psychopaths/sociopaths are especially good at charming first impressions. I’ve met people who have had a sense of something being broken or alien in them that I’ve avoided them after what should have been a charming exchange.


      • I have met a sociopath, and although I usually tend to avoid ‘charming’ people as well, he was too attractive and too cunning for me to rationalize at first. Incredibly self-confident and deluded, entitled and aggressive. The situation I had found myself in was scary in the end (nothing that bad ended up happening thankfully) but observing his psyche was fascinating.

        A lot of sociopaths actually become CEOs because of their charm, ability to detach themselves from others, and irrational confidence.


      • I find that the dissonance comes from the intuitive recognition that there’s no depth, no recognition of character beyond the superficial. I consider myself charming and I practice detachment as a psychological/spiritual tool for interactions and contemplation. My confidence isn’t irrational, it’s hard won and considered and im also conscious of where I am wounded by the world and how it affects me. A sociopath studies and mimics as a tool to get by with the world.


  4. It’s not morally ambiguous at all, it’s morally offensive and that’s that. All this grey area nonsense is just cheaters trying to balm their conscience. Does he love his girlfriend? Maybe. But he loves his ego more. Not you, his ego. Affairs are exciting because they’re hidden and secret and new. Put them in the glaring light and I will go out on a limb and say they never last. They may stay together but they’re broken. If he had told her he’d like to touch you or he was going to…she’d have kicked him out I hope? You’d get him. Would you keep him? I doubt it. He’d do the same to you or you to him or you’d see what she finally saw which is he’s an ego on legs. Humans are fallible. I cut them plenty of slack in being tired, irritable, grumpy, moody, depressed and anxious. Cheating? That’s not a mistake that’s a choice. It’s a choice plenty of us are above no matter the provocation. Do you think rape is just a human failing? Or murder? They are equally common in human history. But we don’t consider those mere mistakes or failings. Nor is cheating.


    • Humans are creatures that enjoy categorizing and defining, and unfortunately life is not as black and white as we’d like it to be. Is there anything wrong with him loving his ego (himself) more than someone else? I don’t think me as an individual has much to do with the situation. It was a raw and safe moment (couldn’t progress) and I think that contributed more to the excitement than us as individuals. I had no intention of ‘keeping’ him beyond those moments, and I doubt he had any thoughts of that in regards to me.

      Is it possible for two people to only ever have desires for each other? Has this ever actually been shown in human history? Modern concepts of love are relatively young, and even so the fidelity concept plays a lot off of patriarchal control of women and the evolutionary fear of uncertainty of paternity. Not to mention our insecurities which we project onto those we are with.

      Keith is one of the kindest people I know. Always willing to help, always generous and kind. This is where I have a hard time believing anything is so cut and dry. I’ve witnessed him being a great person…does one act negate all that? Even if that act was more serious than cheating, such as rape or murder, does that erase every good deed someone has ever done? I don’t take rape or murder lightly. But it takes a certain kind of weakness and instability to be able to commit those things, and that is sad in its own way and, as I said in my other comments, perhaps may be better dealt with rehabilitation over retribution. Retribution doesn’t change what happened. But rehabilitation can help change what could happen in the future.


      • LOL at you defending cheating. Really. Right and wrong in that sphere really are that simple and always have been. The only thing that’s changed is now it’s equal opportunity and wives now have a choice how to respond. But the morality has not changed. Something isn’t right because many believe it, nor is it wrong because many condemn it. It is right or wrong on its merits.


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