Dear Wendy
Dear Wendy

“Should I Tell My Boyfriend I Cheated?”

For the past four years I have been an exemplary girlfriend. I have never cheated, I was very understanding and respectful, and my only sin was to be a little bit jealous. My boyfriend parties a lot, he travels a lot for work, and he is a heavy drinker. He works with a lot of hot, young people who usually drink a lot as well. I always had my doubts in regards to whether he was cheating or not, though he always said he would never cheat on me because he would never want to lose me.

Regardless of his loyalty claims, I always remained skeptical. I read a lot about human nature and infidelity and came across something called “monogamish”. It means being in a relationship but understanding that your partner might stray sometimes without it being the end of the world. It was perfect! For me, it was the way of getting that pressure off me. I could understand how he could fuck up one night and I thought I deserved the same leeway. I proposed it to him at various points, but he would always dismiss it, and kept saying he would never cheat on me, regardless of how drunk he got.

Recently, I decided to study abroad and, as the depature date approached, we discussed what to do with our relationship. He decided he did not want to break up or have a monogamish relationship (my preference), so he is considering coming to live abroad with me or having a normal long-distance, non-cheating relationship.

There is a problem, however: I already cheated.

Recently, I met a guy (who was really too hot for my taste) who asked me out. I told him I had a boyfriend back home, and he said he did not care because he enjoyed talking to me and he could be my friend. I told myself I needed a friend and so I went out with him and we had an amazing time; we talked over wine and laughed and everything was fine. Then he said there were some friends back in his house and asked me if I wanted to meet them. I said yes, but, when we got there, everyone was asleep. What a great time to leave immediately with a clean conscience, no? Well, by that time I was drunk, I soon got even drunker, and I then had unprotected sex with this guy. And now I regret having sex with this person because it might hurt my boyfriend.

The question now is whether to come clean. I am sometimes unsure of wanting to be with him forever, but I think that is a normal feeling in any relationship. And sometimes I think this is just a phase and we can be happy again in the future if we can endure this separation first. But even if we are not together anymore, I don’t want to destroy the image he has of me. Plus, his parents love me, his brother loves me, and I absolutely love them. They are all family to me, as he is.

However, he might decide to come be with me, and shouldn’t I give him the chance to decide based on the truth?I was thinking that if/when he tells me he wants to come, I should tell what happened and be prepared to lose my family in the process, but that otherwise I should remain silent.

I have no idea is this is a good plan or not. Thoughts? — Absolutely Lost Person

My thoughts are you should quit being so damn selfish and break up with the poor guy already. The feeling you have of not being sure you want to stay with him isn’t something that every person in every relationship feels. It’s what people who are in relationships they don’t really want to be in feel. You don’t want to be in this relationship, but you’re afraid of the unknown — afraid down the line you’ll regret losing this person, afraid you’ll learn there isn’t anyone better for you, afraid of making a mistake. So rather than be strong and independent and deal with the fear head-on, you’re cowering behind your fear and making your boyfriend pay the price. You’re cheating on him and letting him continue believing you want him to move abroad with you.

You don’t want your boyfriend to move abroad. You just want him to wait in the wings while you sow your oats, play the field, and decide whether you want him in your life as a partner or maybe just a friend. And that’s super unfair and incredibly selfish and unkind.

You’re young, I get it. This is probably your first serious relationship and the thought of breaking up and losing what has been a formative part of your evolving identity is scary. The thought of sacrificing your relationship with your boyfriend’s family is sad. The thought of his having less than loving, adoring thoughts and memories of you makes you feel bad. Well, yeah, that’s the way breakups often go. They suck. But that doesn’t mean you should continue avoiding one. Everything in your letter — the lack of trust in your relationship, your desire to be with other people, your disagreement about what kind of relationship you both want, the excuses to behave in ways you know are wrong — indicates that it’s time to move on. So, cut the cord and do it. There’s no reason to even bring up the cheating. Simply say: “I love you, but I’ve been feeling conflicted for a while and the recent distance between us has given me the clarity I need to see that this relationship isn’t working anymore. I can’t let you come here thinking that we’re on the same page when we aren’t. I need my independence, and a committed, monogamous relationship is in direct conflict with the self-exploration I’m craving. If loving you were enough, I wouldn’t need anything else, but it’s not, and I’m very sorry for any pain that that might cause you. I hope you understand.”

And, finally: For the love of God, get yourself tested and never again have unprotected sex with some rando you just met, no matter how hot you think he is. It’s almost 20-freaking-16 and with the wealth of knowledge and plethora of contraceptions available, there’s no excuse for putting yourself (and your partners) at risk for STDs and unwanted pregnancies.


Follow along on Facebook, and Instagram.

If you have a relationship/dating question I can help answer, you can send me your letters at wendy@dearwendy.com.

36 comments… add one
  • K December 8, 2015, 9:27 am

    My first thought was apparently also Wendy’s – “The feeling you have of not being sure you want to stay with him isn’t something that every person in every relationship feels. It’s what people who are in relationships they don’t really want to be in feel.” People may feel those things, but then they likely aren’t in the right relationship. So I agree it’s better to move on.

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    • SpaceySteph December 8, 2015, 11:47 am

      Yeah I think that feeling like you don’t want to be with him forever is normal, in that it means you want to break up and that’s a normal thing people do. When people say relationships take work, its because life takes work and sometimes takes priority too much… not that you should have to work to convince yourself to stay with a guy on a regular basis.

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  • laurahope December 8, 2015, 9:29 am

    Believe it or not, it is actually possible to not want to cheat on someone (even if you’re drunk). Because you really don’t want to be with anyone else. Because you share an intimacy with that person that you just wouldn’t have if you were being dishonest and deceptive. Because ultimately the benefits of that kind of commitment outweigh any momentary pleasure or excitement.

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  • PumkinSpice December 8, 2015, 9:37 am

    She did all this research on “monogamish ” relationships, but none on the consequences of unprotected sex? Lol
    Okay, all fun aside, LW, please listen to Wendy on this. She is right. You are living abroad, doubting your boyfriend, and sowing your wild oats. You need to end this relationship and explore the world around you. You are young. The fear of the unknown is scary. It is so scary that we stay in relationships that are no longer working or are not good for us. Stop trying to rationalize this situation and see it for what it is. This is ending or over. Your boyfriend seems more committed then you, and you don’t trust him. Go be young. Enjoy your experiences that lay ahead, but be safe and smart about it. People don’t have to get married and settle down at 18 anymore. You have a whole new life ahead of you. Go explore it while being independent and free to do so.

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  • ktfran December 8, 2015, 9:55 am

    As usual, Wendy is absolutely spot on. Seriously. LW, listen to her.

    Please know that there is nothing wrong with the way you’re feeling. What is wrong is to continue down this path trying to make your boyfriend have the kind of monogamish relationship you want, and he clearly DOES NOT. You’re being selfish because you’re scared. But if you truly wanted to be with him, I promise you that you wouldn’t want to stray. The kind of relationship you want only works when both people want it.

    I have been where you are. Only, I was engaged. I’ve told the story here several times so I won’t go into it. But I can promise, you won’t regret your decision.

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  • Diablo December 8, 2015, 10:03 am

    Oh, please, LW. Your mistrust of your BF is pure projection, based on your knowledge that you don’t wish to be and have not been faithful. Your excuses are simply lame. You wanted to bang some hot random guy and you didn’t have the integrity to be honest with your BF and break up with him before you did it. So break up with him now and let him find someone who deserves the love he has to offer. And sort yourself out before you break the next guy’s heart. It’s not a problem if you want “adventure.” Do what you like. Just don’t toy with people’s emotions because you are too chicken to own your decisions.

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  • dinoceros December 8, 2015, 10:17 am

    As has been said, break up with him. You don’t need to rub it in his face that you cheated, but just let him go. In the future, learn how to be upfront with yourself and your partner about what you want. As in, don’t conjure up some erroneous assumption that your partner is going to cheat on you in an attempt to give yourself permission to cheat.

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  • othy December 8, 2015, 10:31 am

    I’ll give you the same advice I gave my brother’s (now ex) girlfriend. Just because you love his family (and his family loves you back) does not make your relationship with the guy worth it. Yes, you may be like family, but that doesn’t mean your relationship with him is working. You’re not happy and you haven’t been for a long time. You’re young, and you’ve been with him forever, and you’re scared of losing the benefits you have in the relationship. However, your unhappiness means that it won’t work long term. It’s better to cut the cord now, rather than making yourself (and him) miserable. It will be unpleasant, but you will be fine. And eventually, you’ll find someone who does make you happy and has all of the good that keeps you clinging to the remains of this relationship.

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    • othy December 8, 2015, 10:32 am

      Also, does it make me a terrible sister if I encouraged my brother’s girlfriend to dump him? (In all fairness, she came to me asking for advice. And I never told her she was too good for him, even though she really is).

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      • Raccoon eyes December 8, 2015, 11:35 am

        I dont think you are terrible at all, if it is true. You totally could have just said that she deserves better. Gets around the actual terms of “she is too good for him,” riiiight? Methinks so.

      • SpaceySteph December 8, 2015, 11:50 am

        I don’t think it makes you terrible either. I mean, why would you want him to remain in a relationship when they’re not happy (and if she’s not happy then THEY are not happy, even if he thinks he is)? Would you want him to get married to her, too, and then go through a painful divorce in a few years? No.
        But it’s probably nice that you didn’t tell her she’s too good for him. And don’t tell him that part, either 😉

    • dinoceros December 8, 2015, 11:37 am

      Good points. Plus, she’s worried about her “image” among his family, but whether they think badly of her or not, they will eventually forget about her. She’ll be replaced by another girlfriend, and they won’t even think about her.

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    • Raccoon eyes December 8, 2015, 11:44 am

      I totally agree with your sentiments. It took me a couple of tough breakups back in the day to realize that no matter what, you have collateral damage to other relationships when you break up with someone, but staying in the relationship for the purpose of maintaining these other connections or relationships is NEVER worth it. THis is very much a parallel argument to staying in a relationship due to the time invested in it. Also TOTALLY not worth it.

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  • FormerlyThatGirl December 8, 2015, 10:34 am

    I’m SO using that speech.

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  • va-in-ny December 8, 2015, 10:59 am

    Please, please please please(!!) let him go. Let him know that you’re not “in-it” as much as he is. Let him start to have a life without the false reality that you’ve set for him.
    As someone that has been in your boyfriend’s shoes, the wasted time is the worst part. My fiance was scared to make a decision, one that he knew would certainly mean he would hurt me, and ultimately lose me. So, instead of deciding, instead of being “that guy”, he let both of us continue to live our lives with him in secret… until he couldn’t go through with both weddings. That’s when he fessed up. Throughout all of this, I was planning a cross-country move to be with him, getting all of my ducks in a row for MONTHS. And, planning a wedding.
    When it all came crashing down, I was furious, of course, but losing the relationship wasn’t the worst part. It was knowing that the time I used to plan to follow him meant that I hadn’t considered what I wanted for me. I wasn’t applying for jobs, I wasn’t looking for a career, I wasn’t saving money like I should have been. I had a full year of wasted time because he “couldn’t bear the thought of hurting me.”
    He’s going to be hurt – whether it be now, or later, when you reveal to him that you just don’t like him that much anymore. So have a heart and let him start to live his life on his own terms.

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    • Simonthegrey December 9, 2015, 9:59 pm

      I hope he got no weddings out of that shit show.

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  • RedRoverRedRover December 8, 2015, 11:10 am

    I think the fact that you’ve constantly thought that he was going to cheat shows that this relationship was never based on trust. Which means it’s never going to work, even if you get past this long-distance phase, and even if you get past wanting to sow your own oats.
    I also agree with a couple of the posts above that it sounds like your interest in a “monogamish” relationship was more for yourself than you’re willing to admit. And I can see why, if you broached it to him as “I want to be monogamish because I’m afraid you’ll cheat”, that he would say no. Because to say yes to that would be the same as saying that he did want to cheat, whether he actually wanted to or not. How could he say yes? Not to mention that it sounds like you accused him of wanting to cheat quite a bit, and he’s always had to defend himself against that. That’s not a good basis for a relationship.
    So based on all that, and the fact that you’re unsure of the relationship and you clearly want to explore other guys, you should break up. And do it without mentioning the cheating. There’s no need to hurt him further just to clear your own conscience.

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  • Texas T December 8, 2015, 11:41 am

    What a padded email. Probably just how you are trying to explain to yourself misdeed and feel better about it. It should have read: “I have a boyfriend who says he is devoted to me and I have no reason not to believe it. I cheated on him. I dont know if we will be together forever. Should I tell him?”
    No dont tell him! Just break up with him. Spare him the future trust issues and heartache of that confession. You just grew apart. k?

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  • SpaceySteph December 8, 2015, 11:41 am

    Can I just… what even is “too hot for my taste”??? Like, honestly, he was hot, you had sex with him…now he’s too hot? Is that what you’re gonna tell your boyfriend? He was too hot?

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    • RedRoverRedRover December 8, 2015, 11:56 am

      I think she meant that she doesn’t like to date guys who are that hot. I know what she means, I don’t like to date super-hot guys either. When you’re young, the really hot guys are usually still really into dating around, which isn’t the kind of guy I ever wanted, so it turned me off of them in general.

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  • Ron December 8, 2015, 11:48 am

    Just tell your bf that the long distance has made you realize that you are no longer interested in a relationship with him and MOA. You don’t trust him. You want sex with other guys. You don’t want him to travel to you. That’s all fine, but that means it’s time to end it. It’s not at all fair to keep him waiting for you back home. Also not fair to dump the cheating on him. You have ample reason for a breakup without bringing the cheating into it.

    You seem to use drinking as a personal get-out-of-jail-free card in thinking about your own actions. You wanted to have sex with this guy, you didn’t really want to accept responsibility for doing so, so you got drunk, had sex, and because you were drunk also didn’t use protection. That is running a stupid risk. The bigger issue is you are not being honest with yourself. If you can’t have sex with a guy sober, don’t have sex with him drunk.

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  • bagge72 December 8, 2015, 12:02 pm

    It seems you have spent your whole relationship trying to find ways to let your boyfriend let you cheat on him, and when he never gave you a reason you just went and did it anyways. I don’t know why you stayed with this guy for so long if all you wanted to do is sleep with somebody else. You should just break up with him, and it’s up to you if you want let him know you cheated or not.

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    • tzee December 8, 2015, 3:39 pm

      exactly what i was going to say. The whole letter read to me as “I tried to get my boyfriend to accept cheating, but he didnt , so i did it anyways.
      The OP tried so hard to be set free, why not break up and be free instead of ruining this poor guys life. He should be with someone who is not aching to be with another man. I hate women like this. Let the good guy go so he can find a better woman who understands him and respects him the way he does her.

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      • RedRoverRedRover December 8, 2015, 4:36 pm

        I like how it somehow became a gendered issue. Because guys never cheat.

  • Sue Jones December 8, 2015, 12:48 pm

    He parties a lot and drinks heavily. That’s enough in my mind to have you MOA, enjoy being abroad etc. So yes, come clean with your boyfriend and go be monogamish or broken up or whatever it is that YOU want to be. And always carry a few condoms in your wallet for those “just in case” times.

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  • Juliecatharine December 8, 2015, 2:21 pm

    Lmao this LW just wants to pretend that she’s a delicate little flower who didn’t *really* cheat on her long term boyfriend after spending four years of accusing him of behavior she’s dying to partake in. Sorry honey, you don’t get to play that game. Woman up and be honest with yourself and your boyfriend.

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  • absurdfiction December 8, 2015, 5:03 pm

    Oh hai, is this me from six years ago? I didn’t know that I was so well-traveled, or that time machines had been invented back then. Well, message to past absurdfiction: break up. You are making shitty decisions and making shitty excuses for your shitty decisions. That doesn’t mean that you have to be a shitty person. End it now, don’t drag it out, be super sad, then move on. I promise you, in a couple of years you will look back on this and realize with 100% certainty that you made the right choice.

    PS: if you aren’t sure whether monogamy is for you (and it’s not just this relationship that isn’t working), for the love of god, don’t agree to be monogamous with the next person you date. Sleep around for a while and see if that gets it out of your system. It’ll be fun. Just don’t be shitty to people.

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    • Ktfran December 8, 2015, 5:38 pm

      Absurdfiction, I’m glad you wrote this. LW, I also don’t think you’re a bad person. What is do think is you’re young. You’re with this guy you care about, including his family, and you think he’s “the one,” but you also feel something is missing. Most likely it is. That’s why you want to stray. Cheating isn’t good. But believe me when I tell you I understand why you did it. So… Do yourself and your boyfriend a favor. Break up. Learn from your mistake. If you get the urge to cheat with your next boyfriend, break up before that happens. Personally, I think you should take some time and figure out yourself and what you want in a partner. Learn from your mistakes. Grow as a person. And don’t repeat.

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  • tangerbean December 9, 2015, 10:45 am

    Monogamish relationships only work if both people are in agreement on the situation and he clearly was not ok with you sleeping with anyone else. You cheated, stop trying to justify it, and just cut the guy loose.

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  • Monkeysmommy December 9, 2015, 6:39 pm

    And for fucks sake- STOP using the word monogamish!! It’s not a thing, Gretchen!

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    • RedRoverRedRover December 9, 2015, 6:53 pm

      It is a thing, coined by Dan Savage, I believe.

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    • jlyfsh December 10, 2015, 9:13 am

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      • Monkeys mommy December 11, 2015, 10:04 pm

        It is retarded. One guy coining a phrase in a news article does not make it a real thing, sorry.

      • Skyblossom December 12, 2015, 9:55 am

        Whether you like it or not new words and new uses of words come into language all the time. It doesn’t matter who started it. When it comes into use it is in the language.

      • jlyfsh December 12, 2015, 12:24 pm

        You know what is way worse than the word monogramish? Using the word retarded like you just did.

        And like Skyblossom said you don’t have to like the word, doesn’t mean it doesn’t exist in common vernacular.

      • dinoceros December 12, 2015, 2:20 pm

        Eek. Yeah, monogamish may be a silly word, but retarded is a hurtful one.


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