Dear Em & Lo: I Cheated on My Boyfriend And Don’t Regret It

Dear Em & Lo,

So I am currently in a relationship with my boyfriend of 8 years, going on 9. We have been together since high school and are now in our mid twenties. I love him very much and used to see myself spending the rest of my life with him up until just a few weeks ago.

My girlfriends and I decided to take a little weekend getaway and on our first night there I met the most amazing guy. Instant attraction. We ended up spending the night together which turned into morning. He also ended up switching his flight so we could spend another day together. We met up for the last time and I could honestly say it will be one of the most memorable weekends of my life.

Now I’m scared to face what this means for my relationship. Am I not as happy as I thought I was? Am I settling because I’m comfortable with my situation? I know nothing could ever become of my weekend fling, but now I can’t help to wonder what else is out there for me.

I feel selfish for letting any of this happen, but the scary part is, I don’t regret it because of the amazing connection I encountered. My boyfriend is far from affectionate and does take me for granted at times, so I cant help but feel frustrated with where I am in life. Do I let him go? Do I stay and make things work? HELP!

— Dirty Weekender

Dear D.W.,

We could be like one of those annoying therapists who leans back in their chair and says, “Well, what do you think you should do?” Or, “But what do you really want to do?” But today, we’re feeling kinda prescriptive. Today, we’re going to tell you exactly what we think you should do.

Dump. Your. Boyfriend.

You cheated on him, and not just a drunken one-time thing, but repeatedly, over an entire weekend. Sober, in daylight. In fact, you two actually extended the weekend to make the cheating last longer. Worse, you don’t feel bad at all. In fact, you seem to think that the fact that the cheating experience felt so awesome — um, yeah, it does, but so does sex on meth — is what makes it more than okay. And then you attempt to justify the cheating by saying that your boyfriend takes you for granted.

Er, he takes you for granted?

We get it. You got together young, you never got to sow your wild oats, you’re an entirely different person than when you first met — hell, Miley Cyrus was still Hannah Montana when you first got together. It makes total sense that you’d want to see other people and fuck other people. We don’t fault you for that part at all. Whether or not you two are meant to spend the rest of your life together, this is an indisputable fact: It’s time to take a break, either mini or major.

So, start by breaking up with your boyfriend. If you think you’d like a future with this guy, then you need to be completely honest with him and tell him all about the weekend — because you can’t lie now and expect to get back together with him later. But if you want a clean break and you think this is it for good, then it’s fine to just break up with him and leave out the bit about your sordid weekend. (We hope it goes without saying that if you decide to disregard our advice and stay together with your boyfriend, then you absolutely need to tell him about your major indiscretion.)

You could tell your boyfriend that you just want to take a “mini break,” a la Ross and Jen, but if you go this route, then you have to tell him about the cheating — because in that case, you’re still sorta, kinda together. Personally, we’ve never put much stock in this approach, but we know it works for some people. Feel free to give it a try, but be prepared for a lot of misunderstanding. (We were on a break! It was a mini-break! And so on.)

Oh, and to answer your questions: Yes, we guess you weren’t as happy as you thought you were. Yes, you may well have been settling. Yes, nothing will ever come of this fling. As to what else is out there for you? Casual sex, hot sex, heartache, heartbreak, booty calls, unrequited love, more hot sex, more heartbreak, bad first dates, bad sex, bad dudes, nice dudes you’re not attracted to, hot dudes who don’t return your phone calls — and maybe, just maybe, the man of your dreams.

Now… Tell us what you think you should do.

Couch Potatoes,

Em & Lo



  1. “You… are about to embark on a lifelong journey together and you cannot hope to remain on course unless honesty is your North Star.” Geoffrey the Butler in The Fresh Prince of Bel Air

  2. i thought he was the one. I was fully prepared to marry him. he cheated and it hurts that he never told me, i had to see messages on his phone that were naughty, he made a lame excuse that made sense in the context of the messages and that they never actually met up like the conversation suggested and i believed him because im an idiot. I was always honest with him, always did things for him, and now i cant trust anymore. its hard, it hurts, but what can you do. someday i will find the one, but for now i am alone. He never told me he cheated, but its obvious now. He instantly added her on facebook the next day and it killed me inside. nearly 3 years of loyalty and all i get is a bitter breakup with no explanation. He left it at we can still be friends but i dont care. your an asshole brayden.

  3. Lisa, i am deeply concerned. You need to tell your boyfriend. He is fully committed and ready to walk you down the isle. It will be tough but if you ever loved him enough to say yes when he got on one knee, you need to respect him as a human being and tell him your not ready AND what happened. If you do love your fiance like you say you do, you still need to tell him. If he loves you it will work out, but the betrayal might be too much. He deserves to know because he deserves happiness, ignorance is not bliss. Those who are monogamous will find the true love he deserves, the love of an old and tattered heart is like the coals of that of a fire, un-quenchable. Your love was only that of a flickering light.

  4. Exactly same situation.. being with my fiancee 2 years now, cheated on him 8 months ago and then the other night went to the club the man who i cheated with works and now speaking to him again. I know its not fair on either of them but its really no fun for me either.. its one of the hardest decisions ever. I love my fiancee but i really like this guy. But what if i finish my boyfriend and this guy doesnt want to be with me and i end up alone.. which i probably deserve. I really love my boyfriend though.. argh please help?

  5. ^guinevere

    This is a big problem with people today. “It’s all about me me me and nobody else” mindset.

    To clarify, I’m totally on board that young people should be having fun, and that your needs are important as a human being. After all, how can you make someone else happy if you aren’t?

    But when you can’t draw the line and realize that you aren’t the only person that has wants and needs in this world, especially when in something that involves two people (relationships), and that you can’t have everything you feel you deserve, and you can’t feel happiness every waking moment, it makes me wonder if attempting to connect to anyone else in the first place is worth it.

    I mean, what will they do at the first sign of adversity, run off and look for the next happiness high? What kind of life is that?

    Well, I’m an idiot, because knowing all this still isn’t deterring me from trying to make something work. :/

  6. At the end of the day it’s your life, and it goes on. Why deprive your self of life when its so short. There’s opportunity in every direction either with a new interest, or some other sorts. It doesn’t matter as long at the end of the day your happy.

  7. See girl, you are doing a mistake, by not letting your boy know, if you love him so much, you could had broken up with him, if he didnt take you granted, what made you lie if you can’t respect a relationship. If he is never yours, and you are never his, then you should not keep him, you should tell him and let him go, now his friends are laughing at him, at your friends too, at least he can keep his distance from the guy and your friends so he would not be embarassed from them knowing who he is and how unlucky he is, face the truth, you will aace anything in life.

  8. Most of this advice is not fair. First responsibility is to tell him. Talk about why. Maybe he wants to have the same experience or maybe it is fine with him or maybe he can find someone that will want him.

    Maybe this will spark the two of you to open communication.

    Stay together or part ways friends. Good luck at your crossroads. He deserves the truth from you.

  9. Of course she should dump the boyfriend–she picked him out too young and itches to find out what the world offers. But….

    Whatever happened to “what happens in Vegas stays in Vegas”? to the 250-mile rule? to “no harm/no foul”? Hell, whatever happened to “first do no harm” or an acceptance that none of us is without sin? A relationship that cannot survive a 48-hour attack of lust isn’t one worth having. Go home and shut up.

    Sweetheart, just do what your heart tells you to do. It’s probably giving you good advice about staying or not staying with your high school beau. But don’t talk about your adventure for the sake of some nonexistent “closure” and don’t let some sort of guilt about your adventure make your decision for you.

  10. Rules are made to be broken, monogamy is not for everyone, especially not everyone in their 20s with wild oats to sew.

    The important thing is that you can’t have it both ways: if you try to have the support of a dedicated partner without being dedicated to him in return, you’re not respecting his effort or your own independence.

    It is OKAY to be having this exact discussion WITH your boyfriend, just tell him: “I cheated, it felt really good, I don’t know what this means.” This will demonstrate way more respect for him than dumping him without explanation or lying about how good the affair was to make him feel better.

    If you want to make this work, for anyone, don’t try to manage him, treat him like his own person.

  11. ^ Wow, very different perspective.

    When someone else cheats, I just feel like an idiot for having remained faithful. I’m like, “you mean I played by the rules for eight years, suppressing my desires for other women, for THIS shit?”

    And that’s precisely what makes me feel “cheated.” That’s what fills me with rage. I get over sadness much more quickly than I get over anger. I’d rather maintain my delusions of fidelity if I can.

    I mean, if she found a new guy, I could see where you’re coming from. But this was just a weekend of hot sex. In my opinion that’s gonna be nothing but hurtful to her bf.

    Anyway, the one thing everyone seems to agree on is that she should dump her boyfriend. I guess she knows him best and will decide the best course of action.

  12. Once I was dumped by someone who had no other explanation than ‘I just don’t love you anymore ‘ which should suffice but I would have preferred some meet on them dry bones, a narrative to use for justification. Of course later I found out he had a new girlfriend already. Knowing this would have spared me some of the pain that comes with utter confusion.

    it sounds like you need to break up with your bf at least for now. Perhaps you will reunite in the future and perhaps you won’t. So I beg to differ with the advice given. Be great. Tell him the soft core version of what you did. You might as well be honest since the truth will either come out or your bf will pick up on it. We are not stupid beings. Of course he already knows but is probably in denial, it’s a great defense mechanism. If dumped I prefer the full story even if cheated on because the anger fuels me to get over it. Otherwise I tend to glorify my ex and frantically scan our history for reasons WHY. Also, what’s worse than being cheated on and dumped is knowing that your partner didn’t even dump you for someone else, they just prefer nobody specific to you. Somehow knowing that the other person felt they advanced and met someone more suitable springs hope that you will find someone else too, in a distant future, when you are done hating yourself. There is nothing worse than being dumped and having that itchy feeling you’ve been lied to AS WELL AS broken up with.

  13. I agree with the dump him part, but never tell him what you did. I think there’s a special place in hell for people who extra-wound a dumped partner on their way out the door. “Oh, in case being dumped after 8 years isn’t painful enough, you should know that I also rode some stud in the Vegas for an entire weekend.”

    Plus, all your friends know. You’re making a fool of your boyfriend. That’s the worst part of this. Your friends are either snickering behind his back, if they’re bitches, or they feel really guilty keeping this secret from your basically-decent, doesn’t-deserve-this boyfriend. That’s not fair to anyone.

    You have forced your own hand. There are only two ways out of this: the hard way, or the really hard way. Just dump your BF. It’ll be traumatic enough for everyone without introducing the drama of infidelity.

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