“I Had an Affair With My New Boyfriend’s Brother-in-Law Ten Years Ago!”

I am a 27-year-old woman and for two months have been seeing someone who is 31. We are both at the point in life where we want a family. We really like each other and we fit pretty well. A few weeks ago he mentioned the name of someone I had an affair with ten years ago. His wife caught us. I don’t remember much of that time since it was so dark and I blocked a lot out. It meant nothing to me. I was young and stupid. Anyway, the name came about and he was curious if I knew this guy personally. I lied, but later I confessed and told him that we had had an affair. Well, come to find out the guy is his brother-in-law (his sister’s husband!). After many conversations, I told him that I wanted to do the right thing and apologize to his sister. He told his sister he was seeing me, and his sister said she forgives me.

Now we are still trying to move on from this, but he said that, if we continue to be together, he’s living selfishly since I am going to be a constant reminder to his sister. He is not mad at me, but I feel he has a lot of reservations now (which I understand).

What should I do? How can I help him to move on from this? He asks me to teach him how to feel since he’s just as lost as I am. I am looking for a loophole in this. He loves his sister, that’s a fact. But we want to marry each other, and we’ve even looked at opening a business together, which we still want to do even after all this. Do you think there’s any way this could work?— Sorry About the Affair

I don’t see this working out. You are not only actively disregarding your boyfriend’s sister’s feelings again, but you are putting yourself in direct connection with a man who exploited you and took advantage of you. If you were only 17 when you had the affair and he was a grown, married man, he might even be a criminal. Maybe the reason you blocked out the memories of the dark time you spent with this man isn’t because it meant nothing to you; maybe it’s because it really fucked you up. And you know what would fuck you up more? Making yourself part of his family! And investing time and energy into your boyfriend only to have the relationship implode because your boyfriend’s family won’t accept you. You had an affair with his sister’s husband. Sure, people can forgive, but that doesn’t mean his sister wants to have you sitting at her Thanksgiving table for the rest of her life.

You’ve only been dating this guy two months and that makes moving on a lot easier, which is what you should do, because this relationship will not last. To your boyfriend’s sister, you were, and always will be, the “other woman.” It doesn’t matter (to her) that you don’t remember much of it or that it meant nothing to you. I promise you SHE remembers, and it meant a lot more than nothing to her, and she won’t just get over seeing you with her brother. Your boyfriend knows this and, if he loves his sister at all, he won’t get serious with you, let alone marry you. I’d cut your losses and MOA before this gets really messy.


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


  1. LW, you were 17 years old when you had the affair with the married guy. Not a great decision but don’t blame yourself too much. You were young and stupid.

    Now, your current BF is not that great either. He wants you to teach him how to move on ? Not your job. Either he is ok with it and continues or it would always burn in his head and you guys will not be able to move past it.

    I suggest cutting you losses and moving on. Sometimes it may be the right guy but your past seems to be a big obstacle.

    There are other fish in the ocean who might suit you better without the burden of emotional baggage.

  2. You like drama, don’t you?

    1. Bittergaymark says:

      My thoughts. EXACTLY…

  3. Unwanted_Truth says:

    Who in their right mind would even consider marrying anyone after two frickin months?

    “We want to marry each other, we’ve even looked at opening a business together, which we still want to do even after all this. But you think there’s no way this could work?”

    I mean seriously?!?! After two months? Get your head straight LW , this isn’t going to end well for either of you if this continues at this pace, especially with the other background stuff going on.

    1. Maybe they should have a baby, because that would really fix everything
      (sarcasm font)

  4. Oh, lord, if I had a dollar for every letter writer who said “I feel like this is the one I’m going to marry” after several weeks of dating…..

    LW, at 27, how have you not figured out yet that EVERY RELATIONSHIP feels perfect in the first few weeks? Every new boyfriend/girlfriend makes you feel like you’ve never felt before? That’s hormones, and infatuation. It’s not love. Love comes later, once you actually know each other. And no, you don’t actually know each other after two months.

  5. judge sheryl says:

    This is likely also a bit of ‘you can have anything except that one thing’, so now all you want is THAT ONE THING.

    Same for your bf.

  6. Shooooo girl! Run away from this one! Sister-in-laws can be difficult on their own, add in an affair with their husband? This is a recipe for disaster. It’s still early, you can get out unscathed. I REALLY think your boyfriend will understand.

    Trust me, it won’t be worth the drama.

  7. This is like the thread of the woman whose boyfriend cheated on her after some other woman initiated sex. She decided instantly to forgive him without giving it much thought.
    This is the same. Your boyfriend decides to forgive you and continue with the relationship, like nothing happened. However, this will ALWAYS be there. This is carved to the back of his mind. To him, you’ll always be the one who had an affair with his BIL, the one who made his sister suffer. To his sister, well, you know.
    How do you see this going? Can you imagine family gatherings? Your boyfriend won’t be comfortable seeing you and his BIL together. Things will be AKWARD. This will end. It’s most likely he won’t get over it. If this doesn’t end now, it will, six months from now, a year.
    LW, you should move. This is a very akward situation to be in.


    1. I must have missed something in the letter…

      1. Besides the fact where she mentions at the beginning of the letter, “We are both at the point in life where we want a family.” – a child does not need to be brought into this maelstrom of drama.

      2. Sure, it’s decent general advice if someone’s in a messy situation, but I didn’t get the idea she was actively trying to get pregnant right this minute.

      3. honeybeenicki says:

        In many of these situations, they aren’t “actively” trying to get pregnant but they aren’t doing a good job of preventing it either. I think birth control is great advice in this case.

      4. Yeah, but given that 90% of these letters end with “…and now I’m pregnant” it pretty much always applies.

      5. Bittergaymark says:

        PLEASE!! Every other letter / thread on here is about yet another whoopsie baby… And a LW who is THIS fucked up / delusional is so the type of accidentally get pregnant just to up the endless drama…

      6. honeybeenicki says:

        But a baby will REALLY make him love her! (Ugh). People like this make me twitch.

  9. Avatar photo mrmidtwenties says:

    This relationship is likely to die fairly quickly anyway. Talking marriage and starting businesses together after 2 months is likely a sign that everything is going to go up in smoke.

  10. Marrying the very new boyfriend is a perfect way to enact revenge on the ex married lover – who most likely did take advantage of a teenager. What better way to make him squirm, endlessly, but to have him see you at every family event, birthday, holiday, for the next decade or so.

    1. This is a good point . I don’t think bf is good for the LW or anyone right now as he seems selfish and sneaky and all the stuff she mentions about him is weird. But the older couple have made their own choices, why shy away from letting them see their own choices. 17 is just too weird to me. I would ditch any husband for that even if we had kids.

    2. Honestly if I’d been a part of an affair I too would be endlessly squirming at every family function until the end of time. Imagine being the LW and showing up at Christmas?! Endless gossipy whispering and probably a very chilly reception, whether she was exploited or not.

  11. Juliecatharine says:

    First off, there really is nothing for your boyfriend to forgive you for. His brother in law is a scumbag at best and is the responsible party when the ‘affair’ involves a fucking teenager. GROSS. Two months is way too soon to be talking about marriage and opening a business together. You are not the exception, this is not some epic love story. MOA, you don’t need this kind of drama.

  12. Teach him how to feel?!
    No. I just can’t.

  13. Stillrunning says:

    The boyfriend’s shady, casually asking if you knew the the guy and then after you confess, he tells you it’s his BIL.

    1. Don’t you love it when somebody you want to marry tries to force you to lie instead of just asking a straight forward question?

  14. This is like out of some sort of fiction drama book! Hoping for miracles, teaching somebody how to feel because they are so lost. The lust and passion of a 2 month relationship with the women who helped fucked over your sister. This line though is straight out of the DW handbook for Letter Writers on page 2 about what to do after being in a relationship for 2 whole months. “We want to marry each other, we’ve even looked at opening a business together, which we still want to do even after all this.”

    1. Avatar photo Cleopatra Jones says:

      Ahh, Bagge…you’ve never been in this kind of love. What could you know??

  15. MissAnneThrope says:

    So your bf tells you that he wants to be selfish for “ONCE” in his life. However, you tell us that he doesn’t open car doors for other people, at 31 has never said I love you, etc. I hate to be the one to break the news to you, but this isn’t the “first” time in his life he’s been selfish. He IS selfish. Selfish is talking to a woman about marriage two months in KNOWING that there’s drama. Selfish is keeping you around while TELLING YOU he’s not going to end up with you. Selfish is having someone else tie their income to them, knowing that in the near future things could get very messy.

    You don’t need to be selfish. You need to be self-aware and find a man who is willing to commit to you as much as you are willing to commit to him.

  16. girltuesday says:

    Wendy, you should submit your letters to the Lifetime Movie Channel. Such great material.

    LW, WWS – MOA. This is not going to end well. The sister might be “cool” with it now, but you can bet that it will fade out and resentment will rear its ugly head.

  17. I had a pretty disastrous “relationship” with an older man when I was 15. At the time I really wanted it. I didn’t think it was creepy that this guy took advantage of me until recently. I blamed myself for what happened the most. So I chalked it up to being young and stupid and just shrugged it off and didn’t deal with it…except for the 6 years of depression that followed, not to mention the horrendous mistakes I made in every single relationship that followed. I hope that you can forgive yourself and I wholeheartedly suggest unpacking this in therapy because it’s something that might be affecting you in ways you don’t even notice.
    It’s not coincidence that this guy and his wife showed up for you in such an alarming way, it could be life telling you to deal with this now or else it will keep being a problem. Love yourself enough to walk away and forgive everyone involved including you. But don’t subject yourself to more hardship for such a young relationship. There’s still time to choose you.

  18. “Opens car doors for me” =/= “Automatic husband, father and business partner material”. Agreed with everyone else – even if you hadn’t become entangled with his BIL years ago, you are WAY too hot and heavy, way too fast. Also, you’re 27! Stop thinking about relationships the way high-schoolers do. Star-crossed lover drama is not a part of healthy adult relationships.

    1. zombeyonce says:

      Yeah, that part really bothered me. Those are some seriously low standards. And a guy that says he feels more strongly for you than anyone he’s ever been with after 2 months? That’s a huge red flag when he’s 31. If by this time he hasn’t ever gotten past the infatuation stage with anyone (where it ends and he feels bitter and forgets he ever “loved” her in the first place), he’s either a big fat liar, deluded, or an dangerous combination of both. And the fact that he tested you to see if you would tell him you knew his BIL (a married man who slept with a teenager) is another red flag. This guy is untrustworthy.
      If you are still in love with him after being together for a year, sure, consider marrying and opening a business together (but consider carefully even then). But you haven’t known this guy very long and he’s already thrown up multiple red flags that you’re not seeing. You need to take a step back and consider why you want so much for this to happen. I don’t think it has much to do with him.

      1. BINGO.

  19. Two thoughts. One, “fog of lust”? Is this a thing? I’ve never been able to generate more than, say, a fine mist, though admittedly I live in a dry climate that is not prone to fog at the best of times. Two, and much more importantly, what is this thing where people believe that God intervenes in their lovelife? That they were put in the position of banging some dude by God himself so that they can learn some life lesson? I’m not religious, but do you really think that with 9 billion people on the planet, God is personally directing your little drama? Wouldn’t God (by the standard expressed in scripture) call you an adulterer and fornicator? Did you repent your sin? Not in so many words? My other favourite is when MMA fighters cross themselves as they enter the octagon – yeah, sure, Jesus wants you to beat the other man (or woman nowadays, hurray for equality!) into an unconscious bloody pulp. I know i overuse this word, but Sheesh!

    1. SpaceySteph says:

      Yeah, the biblical punishment for adultery is for both the adulterer and adulteress to be put to death. So… I mean if you think God is taking time out of his busy schedule of creating hurricanes and whatnot in order to take personal action in your love life, he probably should have stoned you himself by now.
      Or, more likely he’s not all that interested in your day to day life and you just happen to live in a town where you are always 3 degrees of separation from your former lover. Maybe, then, the best advice is to move far far away.

    2. Along the line of your comment (2), the Amy Schumer skit with Bill Nye on how the universe is actively directing the lives of upper middle class white women is hi-larious!

      1. Omg you guys are hilarious and I’m going to look for that any skit now. I like the one with the doggy daycare

      2. That one kills me too, plus I think we see too little of Rachel Dratch. Maya Rudolph, Tina Fey, Amy Poehler and Kristen Wiig all deserve their level of fame, no argument, but Dratch’s career has not taken off to the same level, even though she is as funny as any of them at her best.

      3. Ahhh yes I know who you’re talking about. She is funny and a scene stealer. Maybe she needs to set goals? I should search for her on YouTube too.

  20. LW, I agree that you don’t need to be forgiven for this. You were 17 and very young. If your ex was an adult and married, I think you need to talk to your boyfriend about what he thinks about his brother in law and his actions. Does he think the actions were normal? Does he think his BIL is a good person? Honestly, can you really see spending every holiday with these people? I don’t think I could be with a man that would think it was ok.

  21. SpaceySteph says:

    Wow. First of all– your boyfriend’s BIL is a scumbag for sleeping with a 17 year old, and double-so for cheating on his wife while doing so. Let’s just call that for what it is. His wife may have moved past it, and maybe even has forgiven you like she says because let’s face it you were a child and her scumbag husband was taking advantage of you. Honestly, from all this alone, it’s not worth getting embroiled with these people again. This is a part of your past that you’ve “blocked out” because it was so bad. Forget about the constant reminder to the sister, what about the constant reminder to you?
    Also I feel as if it’s not that his name just “happened” to come up, but rather that your boyfriend either knew or suspected that you were the “other woman” and was probing to see how you’d react.

    And secondly, let’s talk about this part: “He hasn’t ever said he loves anyone, never opens the car door for anyone, never has had someone consume his mind as much as I have.”
    I know that society and some terrible romance movies have taught you that these tortured, emotionally closed-off guys are just waiting for the right woman to come along and teach them how to love. But honestly, that’s a load of crap. Him telling you these things is playing into that stereotype, and he probably told the last girl and will tell the next girl the same thing.

    Get out. Get out so fast. Go find a guy who is open and ready to love on a reasonable (not 2 months) timetable, who won’t try to sneak in a “love you” but will actually say it and mean it, and most of all a guy who isn’t closely related to a married man you used to sleep with.

  22. bittergaymark says:

    I’d love to know what the brotherinlaw has to say about all this. How old he is, etc. The most curious part about your whole letter — and other’s have touched upon this — is the whole cat and mouse way your DREAM LOVER fucked with you about asking if you knew his brother-in-law. Had he NOT known about the affair already — he would never have played this game. I suppose he casually mentioned you to his sister and she spilled the beans… But still. Pretty shading of somebody who is totally your SOUL MATE. Oh, the power of your SPECIAL LOVE already seems to be fading, darling…

  23. Another Jen says:

    You made a dumb mistake at 17, and were possibly taken advantage of by an older, married man. You don’t deserve to be raked over hot coals over it 10 years later. And, you don’t deserve to be someone’s sister-in-law’s ‘unpleasant reminder.’

    He’s not doing you any favors in trying to learn how to love you…and by being selfish and pursuing you in spite of his family. Cut him loose. Move on. You can find another “the one” without all of the baggage.


    1. seeing as she was under age I don’t think she made a mistake. I think the man made a mistake (to say it nicely) and his wife made a mistake to forgive him for cheating on her , with a minor. Really gross to me.

      1. bittergaymark says:

        Yeah, but what if he was 18 at the time? Seriously?

      2. Well then fine! I’m assuming he was married and 25 or something . Also, his vows. I want the Lw to focus on the bad in her current partner without seeing anything as her fault

      3. Whether the guy was 18 or 48, even at 17 she was old enough to know it was stupid and wrong to get intimate with a married guy. He was the predator and she the victim, but she was a very willing victim. It would be a very good thing if she learned her lesson from that and stayed away from other women’s spouses in the future, rather than be given the message that she did nothing wrong. It’s not something she should continue to beat herself up over, but it was wrong.

  24. AlwaysALurker says:

    I haven’t commented in a while but honestly this letter has so many glaring issues that keep coming up in other letters. This LW sounds like she’s still 17 because at 27 you should definitely have more mature thought processes than that. 2 months and they’re thinking of marriage and a business! Also, the dreaded “we’re both ready to start a family”… how many kids have suffered from this completely irresponsible mentality. I don’t blame Wendy for focusing on the main infidelity issue because everything else would take a book!

  25. Anonymousse says:

    I’m kind of thinking the boyfriend is fucking with you. How convenient he knew about the affair you had ten years ago, he caught your lie and is dead set on continuing this 8 week old relationship. Either he’s got some serious issues with his sister, or this is an epic troll at revenge from the sister. I don’t know. And that’s ignoring all the other red flags such as business, marriage, kids. Run for the hills.

  26. dinoceros says:

    To me, the bigger issue here is that you’ve already decided you want to marry and start a business with someone you have known for two months. There is a lot more that couples need to learn about each other to determine whether marriage is right for them than can be learned in two months. Anyone can date someone for two months. The fact that it’s gone “well” (I use quotes because this is a huge issue you have encountered) for two months doesn’t mean much. The fact that you don’t know this makes me question your maturity and thus whether you should be trusting yourself to make these kind of commitments at this time.

    I blame rom-coms for this idea that people have that things are meant to be and that makes drama seem romantic. It’s great to follow your heart, but it’s good to use your brain too. Dating someone whose brother-in-law you had an affair with is just a messy, unpleasant thing. Dating is not this mystical thing of fate. Sometimes you need to just say, ugh, this situation is not good, and move on and meet someone else.

    1. bittergaymark says:

      But this affair could be their MEET CUTE… It’s all so Judd Apatow…

      1. dinoceros says:

        I’m sure this will be a blockbuster when it gets into theaters…

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