Dear Wendy
Dear Wendy

“Should I Tell Her I Accidentally Slept with Her Boyfriend While She Was in Jail?”

jail love
I have been friends with this man, “Daryl,” for 10 years. He and I have always been drawn towards each other, but never acted on it, as I was in a long term relationship for 8 years until recently. He and this girl, “Karen,” had a baby, and were together for the first couple of years after having their son. Their relationship was challenging, but they both stepped up to be amazing parents to their son. He discovered she was pregnant after calling to break up with her. After hearing the news, they decided to try and make it work. He is 52 and she is 31. I am 28.

Karen and I were never particularly close, but we were friends and we hung out alone a few times. One night she got drunk and accidentally hit someone with her car. She was sentenced to 4 years in jail. She has been gone for about a year and a half now. About seven months ago, Daryl and I slept together and ended up continuing to sleep together for about five months, before finding out his girlfriend was going to get out of jail early. I never played mom, but I did spend a significant amount of time with their son, and he began to tell me he loved me.

After hearing the news of Karen’s impending return, Daryl broke it off, explaining that he needed to see things through with her. Since telling me, he and I have tried to maintain a friendship (platonic), though we have accidentally ended up sleeping together a few times. I am always left feeling awful, as I know he doesn’t care about me in the way he loves her. He wants to have another baby with her, and he intends to try to give their relationship six months before calling it quits. I’m not sure what she’ll want (and everyone around us says it’s a toxic relationship that will never work). Regardless, this has been eating me up inside, because, despite all of our mutual friends knowing that he and I are sneaking around, she doesn’t.

I need to know whether I should tell her. My fear is that she’s already been through so much, and will be completely helpless in jail, if I choose to send her a letter explaining, confessing, and apologizing. While there is no true excuse for my actions, I was under tremendous pressure at the time, and Daryl and I provided comfort to each other while we were both going through our own issues. She has a hearing about whether she’ll be released in the next week, and I am agonizing over how to deal with it. Daryl and I have distanced ourselves from each other significantly in the last 5-6 weeks, but I fear that, by not telling Karen the truth, I am making things worse for everyone. On the other hand, by telling her, I could ruin any chances they all have of being a family again. She is beautiful and kind, but she initially started her relationship with him in a somewhat similar way – while he was seeing another woman.

Daryl says we’ve done nothing wrong and doesn’t want to tell her, and he says he has no regrets about any of it. He says that he cares about me and wants us to be friends. He says that we had a good time and enjoyed the ride and that now it’s time for him to have his family again. He says he knows I never tried to replace her or be anything other than a friend to his son. He says that we truly care about each other and that is the basis for all good friendships. However, lately, he doesn’t ask how I am (I am having major medical issues), and he only responds in very limited ways, unless he’s been drinking, in which case he’s said he’s miserable not knowing what his future holds, or knowing whether they will have a family or not. He’s in limbo, waiting, hoping. Meanwhile, his son cries for his mommy every night. It’s an awful situation for everyone, and the only true justification we really have is that we were both going through really hard times while we were together and we offered each other comfort and solace during that time.

Finally, I have heard that despite his having feelings for me, he is concerned about our thirty-three year age difference. I do love him, but I know he’s not “the one” for me. I’m not sure she is either, but only they can know that, and they do have a son together who is almost 4. I’m just lost as to whether I should tell her or not. I know he and I can’t continue, despite my loving him, for a number of reasons, mainly our age difference and the fact that he doesn’t love me, but I don’t want to ruin their future so that I can clear my own conscience. However, most of our mutual friends know (20 or so people), so it’s likely and inevitable that she’ll find out anyway…. So, is it better to hear it from me or from someone else? — Sought Solace While His Girlfriend Was in Jail

You’ve used a lot of language here to avoid taking responsibility for your behavior and the effects of your behavior. You “sought solace during a hard time,” you and Daryl “accidentally ended up sleeping together,” and then you “ended up continuing to sleep together.” Let’s be clear: there was no accident here. You didn’t just “end up” having sex. At some point, you made a conscious decision to be intimate with this guy. And you made that decision over and over and over for five months while his girlfriend and mother of his child was in jail. Your going through a hard time and “seeking solace” does not “justify” what you did. There is no justification. It was morally wrong and you know it, despite Daryl’s argument that it wasn’t. Daryl is a fucking loser and a creep and in no way worthy of the emotional anguish you’ve devoted to him.

Frankly, all three of you sound like hot messes and I feel deeply sorry for the young kid in the middle of it all. But the truth is, he — and his parents — are not your concern. His father isn’t because you will never have a relationship with him, nor will you two ever have a true friendship. Daryl has used you. He has no respect for you. You were just someone to keep him occupied and distracted “during a hard time.” And if Karen was ever a concern to you, you wouldn’t have fucked her boyfriend over and over and over for five months while she was sitting in jail. You have done enough at this point. Please move on.

Do not try to justify a letter to Karen. Like sleeping with her boyfriend, there is no justification for that. Hearing from you while she’s in jail that her boyfriend cheated on her with you will not be easier for her to handle than hearing the news from mutual friends when she gets out. Let her find out from people who might actually give a damn about her and not have purely selfish motives for sharing the information with her. Move on.

It sounds like you have enough going on in your life to occupy your thoughts and focus without the added burden of this dysfunctional family. I hope that you have a support network — friends and family — that you can begin (or continue) to seek comfort and solace from instead of toxic Daryl (and other predator-type men like him). Please continue distancing yourself from Daryl and turn instead to people who actually care about you for the support you need. Delete Daryl from your life and alert mutual friends that you do not want updates on him, his girlfriend, his son, or anything about his life and relationships. And please, start taking responsibility for your actions and behavior. You know this man is not good for you. You know he is bad news. You know that keeping him out of your life is as simple as staying away from him. Stop “accidentally ending up” in his path. Get off that road and start traveling in a direction where you can be sure you won’t bump into him. I can almost guarantee that path will lead to better things than the one you’ve been on anyway.


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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.

36 comments… add one
  • Laura Hope December 15, 2014, 8:32 am

    The good news is that you’re guaranteed to get on the Jerry Springer show!

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  • Lyra December 15, 2014, 8:40 am

    What’s with all this “accidentally” sleeping with someone crap that’s been on here lately?? There was a letter not too long ago with the same thing. You DON’T “accidentally” sleep with someone.

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    • Miel December 15, 2014, 9:09 am

      Oh do you remember those MTV commercial/psa “sex is not an accident” ? It was like people getting into a car accident, then flying in the air, falling onto each other exactly in the right position for “accidentaaaaaaaal seeeeeeeeex !!!”

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      • Lyra December 15, 2014, 10:23 am

        I just fell over and over and over again!!

  • TheRascal December 15, 2014, 8:52 am

    This question was definitely posted in the forums, however in that posting, Daryl and the LW met when she was 16. This detail stuck out to me as I found it skeevy that an adult — a 42 year-old — would strike up a friendship with a 16 year-old. It seems like this guy is of questionable character to me, likely a manipulator.
    LW, follow Wendy’s advice please.

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    • Lyra December 15, 2014, 8:56 am

      Oh yeah…forgot that detail. Soooo creepy.

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      • TheRascal December 15, 2014, 9:02 am

        I find it interesting that in this letter, she changed her age so that when they met, she was legally an adult. Even at 18 (which I don’t believe is true), it still makes it off to me. I’m trying to figure out in what scenario a high school senior or college freshmen is hanging out with 42 year-olds. If anyone can enlighten me with a scenario, I’d be willing to listen. I’m really having trouble coming up with one that doesn’t indicate that this guy is sketchy.

      • Miel December 15, 2014, 9:14 am

        I had a friend who would hang out with men in their 30s when she was 16. Basically she had a fake ID and would get in clubs fairly easily with her friends. She would become friend with the people working at the club, which helped her make sure she would get in every weekend. Her first boyfriend was one of those guys that worked at the club, she was like 16 when he was 33 or something. Strangely they were together for like 1+ year. He met her parents and everything.
        I’m sure there’re another 100 ways to meet inappropriate friends.

      • TheRascal December 15, 2014, 9:19 am

        Let me amend — I’m interested in a scenario where it doesn’t feel weird or creepy or even predatory on the adult’s part.

      • kare December 15, 2014, 12:38 pm

        I had a friend in high school who had a crush on her dad’s friend. A 16 year old with a crush on a guy older than her isn’t that weird, but when she announced they were having a baby right after her 17th birthday…

      • taurons December 15, 2014, 6:54 pm

        Rascal — I actually had a friend when I was 18/19 that was 40-or-so and it wasn’t creepy (anecdotal, true, but you asked for a scenario). I was fast-tracking in a field that involved a lot of older people, including running some pretty big events, and he and I kept running into each other (he was generally a guest at said events and even hired me to run one on behalf of his office). Eventually we started hanging out (with his then-girlfriend and my then-boyfriend) as friends outside of our mutual-work-stuff.

        The outside-work hanging out started when he and his gf were having a house warming party and thought to invite me as a nice gesture because of the work I’d been doing on behalf of his firm/mutual contacts. (Also, turned out the gf and I hit it off really well – she had just finished grad school at 30 and I was in under grad in the same field – and she and I remain friends to this day, many years later).

        So, long story not-so-short, it can happen!

  • mrmidtwenties December 15, 2014, 9:02 am

    Whenever people say accidentally slept together, I think of it how we’re supposed to call “car accidents” collisions, and this is clearly a both at fault collision.

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  • Dear Wendy December 15, 2014, 9:10 am

    Here’s the link to the forum thread. I hid it for a few days because I only saw it right after I finished writing the column and I didn’t want everyone to chime in the forum thread and then not chime in here.

    One of my pet peeves is when someone sends a letters for advice to me and then immediately posts in the forums. Sometimes, like in this case, I don’t see the forum thread until AFTER I have taken the time to write a column answering the original letter. Not a huge deal, but a little annoying.

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  • honeybeenicki December 15, 2014, 9:41 am

    I accidentally went on a date once (he knew it was a date, I didn’t). But I don’t think I’ve ever managed to accidentally sleep with someone. I’m not even sure how that would work.

    But seriously, break off this friendship or whatever it is with Daryl and move on with your life. And absolutely do not write her a letter! Making someone else feel bad to ease your own conscience is not ok. Yeah, she’ll probably find out from someone else, but hopefully it will be someone who is telling her because they honestly care about her and not to get rid of some guilt.

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  • mylaray December 15, 2014, 9:47 am

    Agree with Wendy. Also, I’m not sure why you would want to even be friends with someone who drinks and drives, and hits someone. Is that harsh? I just see that as incredibly irresponsible, especially for a parent of a young child. And I have no idea why you would want to be friends with someone much older when you’re 18 (or supposedly 16 like the forum question). Daryl is creepy. You got yourself into this mess and you have to own your behavior. But please just get out of the drama and live your life.

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  • FireStar December 15, 2014, 10:26 am

    You want to do the right thing now? Stay away from her and from her old leach of a partner. Your punishment is exile…not some dramatic confession you not-so-secretly hope will destroy their relationship leaving the way clear for you to hook up with a creepy, old man you already know doesn’t want you…all under the guise of doing it in the girlfriend’s interest. What the hell. And who cares about your age difference? He doesn’t. His old behind started a family with a woman only 3 years older than you. And he was quite happy to have sex with you when it was convenient to him. This has nothing to do with age. This has to do with him not caring about you – he does however want the option for sex again if things go south with his girlfriend. You don’t have a special love with him. He doesn’t ask you about your medical issues because he doesn’t care. The truth is he doesn’t want you. Why the hell you want him is something you should address in therapy.

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    • Muffy December 15, 2014, 6:42 pm

      Also just want to point out its not a 33 year age difference as the letter writer says – it’s 23. Still a big age difference. Also he is willing to have a relationship with someone only 3 years older than you – so a 21 year age difference – it’s the same thing LW – the “age” excuse is just another reason to keep you placated so you don’t start getting angry. He is not interested in a relationship with you – otherwise it would have happened in the 10 or so years you’ve been interested in him.

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  • captainswife December 15, 2014, 10:28 am

    I know this is incidental to the thrust of the letter, but I HAVE to chime in about the callous way the writer handles the jail sentence…”Yes, she was driving drunk and, well, hit someone” …um, this woman Karen is a criminal with poor judgment herself — and it’s as though the writer doesn’t even recognize THAT bad behavior for what it was!

    I’m seriously shaking my head in disgust over this whole thing.

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    • honeybeenicki December 15, 2014, 10:34 am

      That was my first thought when I read that. I work for a police department and handle all of the 1st offense drunk driving cases and provide backup for all other drunk driving cases and it is a conscious decision to get behind the wheel when you’ve been drinking.

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  • Amanda December 15, 2014, 10:36 am

    I’m just going to respond to your question since, quite frankly, anything I say about this clusterfuck of a situation is bound to help: no, do not tell Karen.

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  • bagge72 December 15, 2014, 11:30 am

    I have a feeling that after accidently sleeping with this fella for so long, that the only reason for you to write her a letter and tell her about it, is because you are hoping she will break it off with him, and then you can be with him, since you think he loves you. I don’t believe you have this girls best intentions in heart at all. By telling her you might break them up, but you will definitely lose his friendship/penis, and she is going to be really pissed at you too. There is always a chance that he is telling you the truth, and that he was allowed to sleep with other people, while she was locked up, but she just didn’t want to know about it.

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    • Diablo December 15, 2014, 11:54 am

      Is a friendship/penis what you give a girl to tide her over until you are ready to give her an engagement/penis?

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      • bagge72 December 15, 2014, 1:09 pm

        Hahaha I think it is what you give the girl who has been in love with you since you been 16, but don’t want to be in a relationship with her.

  • bagge72 December 15, 2014, 11:33 am

    Also I love how this LW thinks everything crappy that somebody she knows did is an accident. Oh she accidently got drunk, drove, and crashed. Oh I accidently slept with this guy. How about owning up to shitty situations.

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    • Addie Pray December 15, 2014, 3:28 pm

      I accidentally ate two plates of pasta and had two glasses of wine at lunch. It happens!

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    • cakemonster December 16, 2014, 1:22 pm

      I accidentally ate that entire large pepperoni pizza all by myself.

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  • Diablo December 15, 2014, 11:53 am

    Among the profound and lasting contributions made to culture by the Jewish people is the very handy and seemingly universally applicable phrase, “Oy vey.” Another is the word “schmuck.” As in “Oy vey, LW, don’t be such a schmuck!” Drop all these people right nowand never look back. GTF outta the whole situation. And try to learn from your mistakes and live with some integrity in the future.

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  • Moneypenny December 15, 2014, 12:40 pm

    How does a person accidentally have sex with someone? Do you trip and magically fall on top of a penis? Yeesh.

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    • Diablo December 15, 2014, 1:26 pm

      Have you ever seen the SNL sketch “Appalachian Emergency Room,” in which all the patients claim to have somehow managed to fall “brown eye down” onto various cylindrical household objects? I was using Brown Eye Down as a band name for a while.

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      • Moneypenny December 15, 2014, 6:33 pm

        Nooooo, must google it!

  • RedroverRedrover December 15, 2014, 12:48 pm

    I like how she subtly tries to influence us into thinking it won’t work out between Karen and Daryl. “He discovered she was pregnant after calling to break up with her”, “I’m not sure what she’ll want (and everyone around us says it’s a toxic relationship that will never work)”, “but she initially started her relationship with him in a somewhat similar way – while he was seeing another woman”, “I’m not sure she is either (“the one”), but only they can know that, and they do have a son together who is almost 4″.
    LW, it doesn’t matter. It doesn’t matter whether they stay together or break up? You know why? Because he’s made it clear he isn’t interested in you. People who are interested in you ask about your health when you’re having major issues. People who are interested in you don’t cheat on their gf with you and then dump you when she comes back. People who are interested in you don’t outright tell you that they don’t want to be in a relationship. He’s telling you what he wants, listen!
    Also, I find it hard to believe that you seriously think it might be worse to not tell. It sounds like you’re not even actually friends with her – you say you only hung out alone a few times. If you were best friends then maybe this is something she should hear from you, but you’re not. You’re a friend of her boyfriend’s. You clearly only want to tell because you think somehow you’ll end up getting this dirtbag for your very own. But I’m pretty sure that he’s going to be really pissed at you if you directly cause the breakup of his family. A family that he’s clearly trying to be with, and wants to add to.
    The only innocent one in this is the little boy. His mom’s hopefully coming home, and his dad is planning on staying around too. Can’t you just leave it alone and hope that at least one person comes out of this situation happy?

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  • Mr. Cellophane December 15, 2014, 2:22 pm

    I hear banjos. Does anyone else hear banjos?

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  • fast eddie December 15, 2014, 3:40 pm

    Yes the LW is shirking from the responsibility for her actions but this guy has been using her for sex and child care while his “wife” was/is in jail. Plenty of drama, guilt and bad behavior to pass around. It’s past time to MOA, so do it ASAP.

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  • Eve December 16, 2014, 5:30 am

    Are you looking for our approval to write the letter to Karen because you know fully well this will erase any sort of chance of them being together when she gets out of jail and so you can again be there for Daryl (ie start sleeping with him again) ? This is what it seems like to me. You haven’t taken responsibility for your actions for such a long time, what makes you all of a sudden be so insistent in coming clean to his girlfriend?

    You’ve done something immoral and are avoiding properly taking responsibility for your wrong doings. It’s probably too late and a bit pointless doing it now anyway, so at least detach yourself physically (and with time, emotionally too) from this “family” and start building healthy relationships with people who will actually truly care about you during your medical problems and other life problems. And who aren’t lying and cheating on their family to do so! You’re 28 years old for God’s sake, you deserve a healthy, stable, well-balanced relationship with someone, stop looking for the drama with a 52-year-old cheating guy with a kid and a girlfriend in jail.

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  • JenjaRose December 16, 2014, 11:47 am



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  • Taylor December 16, 2014, 12:25 pm

    Waiting for BGM comments on this one; it has the trifecta – cheating, a kid, and hitting someone while drunk driving.
    Oy LW. Aim so much higher. This guy is a loser, and you’re all acting like jerks. I’ll second all the comments about how things don’t happen “accidentally”.

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