“I’m Sleeping With My Married Boss and Landlord”

It’s time again for Shortcuts. For every question, I’ll give my advice in just a few sentences because sometimes the answer to a person’s question is so obvious and the need to hear it so great that being as clear and frank as possible is simply the best way to go.

I have started seeing my boss who happens to be married. I go for drinks with him and his wife, and I also rent a room in their hotel. I have been with this man 3-4 months now and we have done pretty much everything, but, after becoming friends with his wife, I feel I need to end our affair. At first, she didn’t like me so I was not bothered, but now I am friends with her and I feel like what I’m doing is wrong. I don’t want to leave my job, though, because I love it and I like them as bosses. I also don’t want to move out as I like living in the hotel. Can you please help or provide some advice with what I can do? — Bothered By It Now

Sorry, you made your bed here. If you end your affair with your married boss/landlord before you line up a new job and a new place to live, there’s a good chance he’ll throw you under the bus by firing you and kicking you out. He’ll just tell his wife you came onto him and they can’t have someone like that living under their roof and working for them. Find a new job and a new place to live and get out. And next time, don’t screw a married man… even if you DON’T like his wife.

My boyfriend of seven years and I recently broke up because I had a fling with my ex-husband. I am now pregnant and the possibility of it being my ex-boyfriend’s is very high. He currently has a new girlfriend who knows about me and can’t stand the fact that we still talk. My ex-boyfriend calls me numerous times a day and says he wishes things were different. He is there for me any time I need him, and I want our relationship to work out in the long run. He says we are done, but he still gets extremely jealous of me being friends with other males. Why is he jealous when he is roaming around in public displaying his new relationship? He isn’t sleeping with his new girlfriend because he doesn’t find her physically attractive, and he sleeps with me on a daily basis. I’ve tried to stop this, but there is just too much attraction in every way with us. Is there a chance we will work things out? — Longing For Ex

Good God, please do not bring a baby into this dysfunctional clusterfuck. Just, please, don’t.

My man and I work at the same job. He knows every new face in the building. He looks for these women and they look for him. He says nothing is going on. If I see him, he
continues his conversation with them and I feel invisible. Not once has he introduced me to these other women. They watch me and I watch them. I feel as if I am being mentally abused. Should I consider ending our relationship? We have been living together for 14 years. He will turn 60 soon. Is male menopause part of his problem? — Feeling Invisible

No. But have you considered that regular menopause could be part of yours? To feel mentally abused because your boyfriend isn’t introducing you to people is… well, it’s not healthy. Also, why wait for your boyfriend to introduce you to these women? You work with them, too. So go up to them and, “Hi, I’m Jane and I work in HR. I think you’ve met my boyfriend, Rick, who works in receivables, but you and I haven’t been formally introduced yet.” Do that a few times and I promise you won’t feel invisible any longer.


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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. Avatar photo Raccoon eyes says:

    What. The. Frickity. Frack.
    Wow, just wow

  2. Facepalm Friday!

  3. LW1, I am so jealous! I’ve always wanted to live in a hotel. Somehow you pulled it off, AND you love your job and your bosses. Do you know how lucky you are? Unfortunately you made the mistake of shitting where you eat. I’d tell the husband that you need to break it off because you have become such good friends with his wife. Maybe he’ll understand and you won’t have to change your employment or living situation. Buuuuuut I doubt it. So you should probably start looking for a new job.

    1. Avatar photo Addie Pray says:

      Unless it’s a crappy hotel like in that movie Hateship Loveship with Kristen Wiig. Also that movie was so dumb, imho.

      1. I didn’t see that movie. But yeah, I wouldn’t want to live in a place of questionable cleanliness with possible bedbugs, roaches, dead bodies, etc. or in a state of general disrepair. But it doesn’t have to be fancy either! I’d live in a solid business hotel like a Hilton Garden or Hampton Inn.

      2. Avatar photo Addie Pray says:

        I had a friend in law school who lived in an Extended Stay (throughout law school). I thought it was cool but also weird. Plus it cost like $250 a week, which seemed crazy expensive at the time and for the area.

      3. I lived in a hotel for a few months in high school (house fire) and in a hostel in China for a month – both made for some good stories, but I would not recommend living in a hotel long term, regardless of quality…

  4. RedRoverRedRover says:

    Ugh. These are starting to just make me sad. People! What are you doing?!?!?!

  5. Does LW3 work with all women or mostly women? Otherwise I actually don’t think she’s that crazy in being uncomfortable that her bf seeks out the women at work to talk to – seems like flirting to me and i would feel uncomfrtable too if the guy I was with did that. I don’t think she’s menopausal for feeling jealousy.

    1. something random says:

      Feeling uncomfortable is one thing. If boyfriend is ONLY seeking out women and doesn’t converse with men in the building, a lot of people would feel insecure with that situation, especially if boyfriend doesn’t acknowledge you in the conversation. But feeling insecure is VERY different from being mentally abused. Labeling it abusive and talking about male menopause makes the lw seem dramatic. Letter writer doesn’t mention any attempt to join the conversations or talk to her boyfriend about her feelings and get his take on things. She needs to seek out more info and make more of an effort before jumping to conclusions. I highly doubt her boyfriend is sleeping with every friendly women in the office. Of course you never know. There might be some general dissatisfaction in the relationship playing out here.

    2. I think it was her language that made her seem paranoid/more than normal-jealous. “They look for him and he looks for them! Like heat seeking missiles!!” When everyone around you is seemingly plotting, it *might* be time to reevaluate your perspective.

  6. LW3 I’m wondering if perhaps you are close to 60 yourself and maybe were taught that women weren’t allowed to speak up in relationships? Like Wendy said if you want to meet these women go up to them and introduce yourself. I do find the statement, ‘they watch me and I watch them’ kind of odd. Do you stare at them and then they together stare at you silently across the office? Should you consider ending your relationship? Maybe, if you’re unhappy. But, if you don’t learn that you have a part to play in your relationship and to use your voice and speak up, you may never find anyone you’re happy with.

    1. Lily in NYC says:

      I was wondering about that “watching each other” comment as well. I kind of picture these other women looking at OP like “get your creepy man away from me and tell him to leave me the hell alone”. I just can’t imagine all these women he’s talking to are actually into this 60-year old dude. And I bet none of them are even close to his age.

      1. Huh? So because he is 60 nobody really wants to talk to him, and he is just stalking these pretty young women who think he is gross? She does say these women seek him out so that really doesn’t seem likely.

      2. lily in NYC says:

        No, that’s not what I meant at all. I’m just trying to make sense of a letter that makes no sense to me. And I’m projecting because we have a creepy old dude in my department who bothers all of the younger female employees and talks about their asses to the guys (who have the good sense to look mortified). Never the ones even close to his age. And they get this look in their eyes like “save me” when he corners them, so I was picturing him when I read this letter. I don’t necessarily believe that these women are “watching her” and “seeking him out”. I think she might believe it herself, but something just seems off about the whole thing and I don’t really know what to think.

  7. Avatar photo Addie Pray says:

    Is male menopause a thing? I should Google stuff before I ask stupid questions but meh I’m tired this morning.

    1. something random says:

      I’m lazy, too. But I’m pretty sure men do experience a big dip in testosterone as they age.

    2. Yes, I believe it actually is.

      1. Avatar photo Addie Pray says:

        Is it what causes men to get hair plugs and buy expensive fast cars?

      2. I think that’s mid-life crisis and tends to happen earlier.

      3. Some of us still have our hair and buy electric guitars because we prefer boom to zoom, but, yeah, you’ve basically got it.

      1. Real missed opportunity there – shoulda been called “MANopause”

  8. stonegypsy says:

    LW1 can’t be a real letter, right? No one could actually believe that sleeping with a married guy is “okay, as long as you don’t like the wife”?
    Sleeping with married boss/landlord just seems like too many terrible simultaneous decisions for an actual person to make.

    LW2 also struck me as just… too much drama to be real. Or maybe I just need to believe that the world isn’t this stupid because I stopped smoking last weekend and that might be my breaking point.

  9. LW1: I don’t get what you really need advice for? Were you looking for Wendy to give you an answer that would help you still sleep with this guy, be friends with his wife (who is also your boss), and keep your job? The only thing you can do is stop sleeping with this guy, but we all know that can’t happen unless you cut ties completely, so you are stuck I guess. Enjoy it until the wife finds out.

    LW2: Get a paternity test, and find out who the real dad is of your kid. Oh and your ex is sleeping with his girlfriend. I don’t get why people think that a guy lying to one person isn’t lying to them as well. Like because he is with you he has morals. What does that say about your personality too, that he likes this ugly hunch back enough to keep in his life, and spend most of his time with, but he is only using you for a vagina.

    LW3: So he makes friends with both of your coworkers, and you just stare them down, and it’s his fault nobody wants to talk to you? But the letter opener down, stop staring, and ask somebody if they want to go get some starbucks with you, because you have their gold card, and have some free shit coming your way, and you can split it with them.

    1. I lost my Starbucks gold status recently. It was a sad day. Use those perks while you still have them!

    2. Avatar photo muchachaenlaventana says:

      Yes this so much!! “I don’t get why people think that a guy lying to one person isn’t lying to them as well”–like hello, people who lie in such big ways (affairs) are generally not really circumpsect in their lying, nor is one of the people they are cheating on/with the special one who doesn’t get lied to. Come on people! Wake up.

  10. artsygirl says:

    LW2: Not sure if you have the right to resent the BF you cheated on having a new GF. Also, how do you know he is not sleeping with his new girlfriend? Did he tell you that? Also, if he finds his GF so hound dog ugly, why oh why would he be advertising the relationship around town? Have to say my bullshit-o-meter is going off. I keep trying to think of advice to get your relationship back but honestly I think it is unsalvageable especially since you cannot say if your ex is the father of your child.

    LW3: Have you talked to your partner of over a decade about the fact that you feel he ignores you to flirt with other women at work? Also, when speaking with him try not to verbally lash out. Put the conversation in terms about your discomfort without sounding like you are accusing him of cheating.

  11. LW3: Come on, introduce yourself! I’ve been to more happy hours and work events than I can count and despite my slight discomfort with putting myself out there and meeting new people, I make an effort to introduce myself to my boyfriend’s colleagues, but especially the ones my boyfriend is talking to. It’s an automatic in if they’re already talking to him! And we might not work together, but everyone that he works with and sees outside the office knows who I am. I’m sorry to say, but you’re doing this to yourself, lurking off to the side like that. If you do introduce yourself and he cuts you out of he conversation, I’d say you might have a problem.

    1. Also, what is with the rationalization for LW2 that this guy is sleeping with her and not his girlfriend? I’ve heard this reasoning in real life too and don’t get it: how do you think he’s lying to her and not to you?

      1. Skyblossom says:

        Because she is so special, the one and only true love of his life. The woman he can’t resist, so he dates an ugly woman just as a cover, one he would never have sex with because he is saving himself for his one and only love, the only one he will ever have sex with for the rest of his life. Or, like you say, he’s lying to her as much as to his girlfriend and having sex with both of them but he is dating the other woman because he doesn’t trust the lw and never will but is attracted to her body and likes having sex with her, and may also like the idea of using her for sex to get even with her for cheating on him.

      2. Oh yes, the “special love” – I always forget about that.

        Maybe in a surprise twist there’s a third woman who he sees solely in exchange for her amazing cooking.

      3. Wish I could be there when he finds out he is going to be a daddy from all of this, and I also wish I could let him know there is a good chance it isn’t his.

      4. Skyblossom says:

        I think all guys should understand, but many don’t, that if you break up with a woman and continue having sex with her that you should always wear a condom or risk being pulled back in by a baby. It can happen at any time but is especially risky after a break up, especially If she has any desire to get back together.

  12. Good Lord.
    LW 1 – These are your choices? START MAKING BETTER ONES.
    LW 2 – In answer to your question – No. Now, pull your head out of your ass and grow up. You’re going to be responsible for another life.
    LW 3 – I’ll cut you a little slack since there’s not a lot of detail. Definitely see a doctor. Also, start communicating with your boyfriend that his behavior makes you uncomfortable.

  13. Avatar photo fast eddie says:

    LW1- Sleeping with the boss is usually a bad idea but it he scratches your itch it’s hard to say no. Now with liking his wife it’s more complicated. If she’s OK with it let the good times roll. If she’s not then getthefuck out of there.

    LW2- amen Wendy

    LW3- OMG I hope you don’t follow DW’s advise literally and be carted off to the funny farm, but the general idea is good. He’s 60 and most men have completed their transition to adulthood by then but maybe he’s a bit slow.

  14. LW1: So it’s okay to sleep with a married man as long as you don’t like his wife? That’s disgusting. You and the husband both deserve to be thrown under the bus. Hopefully a cross town express.
    LW2: Your ex is a lying, cheating, controlling ass. Get away from him ASAP.
    LW3: WWS.

  15. Skyblossom says:

    LW3 I’m guessing that what you are trying to say is that his behavior has changed. It’s not clear whether you’ve just recently started working together and you didn’t know that he talked to the women at work or whether he never paid attention to the women at work until recently or if when he was talking to someone at work and saw you he walked away from them to come talk to you and now he doesn’t or whether he used to wave you over and introduce you but now he ignores you. I think what you are saying is that he seeks out only the new women at work to talk to which does seem odd. Does he also talk to new men at work? Does he appear to be flirting or just talking. Do the women seem comfortable or uncomfortable with him. Without more information all I can tell you to do is to tell him why you are uncomfortable with the situation, specifically what has changed and suggest like many others that you walk up to people he is talking to and also people he isn’t talking to and introduce yourself, not as his girlfriend, but as yourself and let them know you’d be happy to help them if you can or something along those lines.

  16. I feel like Wendy’s advice to all three of these LWs is not gong to be very helpful in terms of future updates and overall entertainment value. So, I’m going to offer alternative advice that i think will lead the LWs to greater engagement in solving their problems, and also what we in the biz call “good television.”

    LW1 – You’re fine. Your timing is a bit off, but now that you are friends with the wife, you should bring her into a hot threesome. The ideal method at this point would be for you to seduce her on your own, but arrange to have the husband walk in, aghast. You can then both attempt to placate him with sex until the three of you are one hot, sweaty love pie. It’s gonna be great!

    LW2 – Clear lines of communication are the key to every relationship. Just explain to your ex-bfs new girl that you are only still sleeping with him because he doesn’t want to do her and you have mad attraction that just can’t be stopped. Also, tell both your ex-hubby and ex-bf that they are the father, and let them duke it out to see who’s worthy of your love. Also, apply to the court for child support.

    LW3 – Confront your husband when he is talking to one of the women. Accuse him of not introducing you to people. Claim that male menopause is the reason he is mentally abusing you by having sex with every woman in the office. You know they are dying to be boned by your 60 year old husband. Make sure to call her a “gold-digging bitch.” (I know you didn’t mention gold-digging, but trust me, it;s more fun this way.)

    1. Cleopatra Jones says:

      Ha ha, ‘sweaty love pie’. Now I have to work this into at least one conversation next week. Bonus points if it’s a conversation that doesn’t have to do with sex. 🙂

      1. If you can use that phrase successfully in a non-sex context, I order you to report back on that conversation. I will award special bonus points in the form of a forfeit. Maybe I’ll let you ask me one question (any question) and i’ll have to answer truthfully. You could have some fun with that. Maybe I’ll take a dare. We’ll see.

      2. Challenge accepted.

      3. (Cleopatra Jones doesn’t get to have all the fun)

      4. No, but CJ clearly gets her fair share of the fun, though….

      5. Cleopatra Jones says:

        I just want to know how many people you need to make a sweaty love pie? Is three the minimum? What if you only have two does, that make it a sweaty love tart? I think I would really like a deep dish sweaty love pie but a graham cracker crust love pie, just seems awful.

        You’ve opened the door for so many questions. 🙂

  17. Sometimes I ask myself, “Lucy, why do you read this site religiously (almost) every day?” And then, days like this come along, and I realize: I just really enjoy having my faith in humanity tested to the breaking point.

  18. Holy wowzers of wowland. Great advice Wendy.

  19. LW1, you messed up when you had the affair with the husband. There are no do-overs here. Your best option is to take responsibility for yourself and move out of the hotel and find a new job.
    LW2, you messed up when you cheated on your (now ex) boyfriend. He decided that your relationship is over and told you so. He still has sex with you because you let him. Your best option is to take responsibility for yourself and move on without your ex-boyfriend.

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