Afternoon Quickie: “Should I Tell My Fiancé I’ve Been Cheating?”

My fiancé and I have been together for a little over four years and living together for about two. He’s a sweet guy who would give me the world if I asked, and I love him. And when he proposed in December 2014, I was ecstatic, but the very next day we had a party at our house and I got really drunk and made out with one of our good friends though nothing further happened. Well, I blew it off as a drunken mistake, but just this past week I slipped up again and went a little too far when flirting with a long time friend/coworker. We didn’t kiss or anything, but we did lie together and fondle one another. We both agreed nothing more would come of it, but my question is: Should I tell my fiancé since I seem to keep doing it? — Engaged and Making Out With Others

Uh, yeah, you should be honest with him. But maybe even more important, you need to be honest with yourself. What’s going on with you that you would cheat on your newly-minted fiancé, not just once but twice? Do you have a history of cheating before these instances, or did the cheating start only when you got engaged? If it’s new, what is it about being engaged that is freaking you out? Are you afraid of commitment in general, or do you have some doubts about your fiancé, specifically, and whether he’s the one you want to spend your life with? Either way, you need to address these issues you’re having, discuss them with your fiancé, and figure out together how you want to proceed. Maybe you need to put the engagement on hold. Maybe you need to actually break up. But one thing you definitely need to do is stop fondling and kissing other people when you’re committed to someone else.

P.S. There’s a huge difference between flirting and lying with someone and fondling him. Again, you need to start being honest with yourself here.


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  1. bittergaymark says:

    Yes. Monogamy is clearly NOT for you…

  2. Um yeah, laying with someone and fondling each other is WAY past flirting. Whether there was kissing involved or not. You need to be upfront with your poor fiancé and you need to figure out why you can’t seem to keep your hands to yourself. And don’t be surprised if he leaves. I wouldn’t blame him.

  3. Avatar photo Addie Pray says:

    How come I never seem to have long time friends and coworkers who whoopsy-daisy end up lying down with me and whoopsy-daisy we fondle each other? It’s not fair. Otherwise, WWS.

    1. Avatar photo Skyblossom says:

      Maybe you just need to find a place to hang out where you can end up lying down.

    2. …Hang on…. wasn’t your last boyfriend a long time friend (or acquantance?)

      1. Avatar photo Addie Pray says:

        Well, he was someone I knew from a long time ago but we weren’t close friends then and we didn’t keep in touch or anything. He resurfaced from the past so, if that counts, then OK this does happen to me! And OK, I can think of 3 coworkers I had a relation of some sort with. So, I retract my comment above. I obviously didn’t give it enough thought, ha.

  4. Laura Hope says:

    One doesn’t accidentally make out with or fondle or have sex with someone. You can’t hide behind that bullshit. Own up to what you’re doing and why. The tone of your letter implies that you’re with your fiance because he’s a good guy and you feel great affection for him–not because you’re in love with him. And you may be more excited about the idea of being engaged than the reality of it. It’s okay if deep down you know this isn’t right for you. But it’s not okay to mistreat him.

    1. You mean I can’t just trip and fall and accidentally sleep with someone? I thought that’s how it worked.

      1. captainswife says:

        Didn’t we have another post recently where someone “accidentally” slept with someone else multiple times? This seems familiar…

      2. Apparently its a legitimate problem. Maybe the government needs to form some kind of committee to address this.

  5. eelliinnss says:

    Please tell him so he can break off your engagement and find someone who will treat him the way he deserves to be treated.

  6. Laura Hope says:


  7. SixtyFour says:

    I would tell your fiance, but only because it sounds like these things have a possibility of getting back to him. You made out with a good friend at your house at a party where chances are other people saw or picked up on clues even if you didn’t kiss him in front of them. And this thing with the coworker also has the chance to spread. If your company is anything like the places I’ve worked at, it will spread. We used to say that the paper mill I worked at made two things: paper and rumors. It only takes one person to tell one other person before it gets out of control.
    It would be much better if he heard this from you first rather than someone else.

  8. I once went on an accidental date. But I have never accidentally fondled someone. Ok, maybe that’s not true either – I mean, I go to a lot of rock concerts and we’re all very close. But we’re rarely laying down.

    1. I’ve been on an accidental date. But, there was definitely no fondling.

  9. Yes, you need to tell him, so that he understands that a) you’re in no way ready to get married, and b) in no way ready to be in a monogamous relationship. I assume he’ll break up with you.
    You talk about the times you cheated like they’re some mysterious thing that just happened, and you don’t know why. It’s really simple – you chose your pleasure over your relationship with your fiance. You saw something you wanted and you went for it, because getting it was more important than your fiance is.
    You want to have it both ways. You want your sweet, “give you the world” fiance, and you want to be able to make out with random guys whenever you want to. You didn’t mention being in a open relationship, so no – you can’t have both. Pick one.
    And while you’re telling your boyfriend what you’ve done, be sure to tell him what his ‘friend’ did. So he can drop the dirtbag who’d make out with his buddy’s wife-to-be THE DAY AFTER THEY GOT ENGAGED.

  10. How would you feel if the roles were reversed and your fiance was the one who did the “accidental” fondling/”flirting”? Yeah, that’s what I thought. Tell him. You owe him that.

  11. My jaw about hit the floor. Wendy had great advice and was way nicer than I could have been. LW, what on Earth were you thinking?! I hate to be Ms. Judgy but…wow. These are not events that just happen. This is not something that people just do. Good luck talking to your fiance, but I wouldn’t expect to keep calling him that after your conversation.

  12. Avatar photo Raccoon eyes says:

    My vote is dont tell him, but definitely break it off- not just the engagement, but the whole relationship. Telling him is only going to absolve you, and only to a certain point. Telling him you made out with someone the DAY AFTER you got engaged and last week laid with and fondled someone (WTF?) is going to do nothing but potentially give him issues and definitely mess with his head for a time. Save both of you some heartache and just tell him that this is not working, that after some soul searching you need to be apart or WHATEVER. Just break up with him.
    If monogamy is in fact what you want, then open your options up to meet someone who makes you so unbelievably happy and that you are so happy to be with that fondling or kissing another dude never even crosses your radar. Someone who makes you want to be a better person and feels the same way with you. Someone you want to spend your life with, not one who you would just say would give you the world if you asked (mainly because you would ever ask, and btw NO ONE says this shit outside of romcom movies and [presumably] romance novels). Grow up, on your own, and let this guy go. It isnt the right fit for either one of you.

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