Dear Prudence

Colleagues With Benefits

How can I get my (older, married) co-worker to hook up with me again?

Mallory Ortberg
Mallory Ortberg

Sam Breach

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Dear Prudence,

I work for a small business and am very close with my co-workers. We often spend time together outside of work. I’ve spent the last few months subtly flirting with a co-worker who is 20 years my senior, but I’ve never attempted anything further as he is in the middle of a divorce, although I am very close with his children. About a month ago, I was at his house while his family was away, and we established that we are attracted to one another. We decided to proceed with a “friends with benefits” situation since our relationship is complicated. We hooked up but did not have sex. At the end of that week, he told me that he preferred the sexual tension and “the thrill of the chase” to our new arrangement, although he did not want to ruin our friendship. I was not interested in that as I felt rejected.

After a few days, I realized that I may have appeared too clingy and annoying—especially since a man in his 40s probably does not want his hookup texting him every day. I am never the clingy one, and it irritates me to think that I was. So I told him the following Monday that the chase was back on. Our flirtatious behavior has since become much more intense, while remaining discreet. It has now become almost a game in my head to have sex with him. I am not sure why. Should I make a move or bring this up with him? I would like to establish that relationship with him, but I am unsure if I ruined it by being too overbearing. Where do I go from here?


Oh, yikes. This letter started unraveling about two sentences in and I’m not quite sure where to start. Let’s start with the fact that your co-worker—a still-married man in his 40s—is apparently in the habit of inviting his twentysomething female colleagues over to his house while his children are away. Depending on your age, this may be one of your first full-time jobs, and it’s worth repeating that this is not normal office behavior, not even for an office that’s especially “close.” I don’t think you were annoying or clingy by texting this guy on a daily basis for a week. I think becoming friends-with-benefits with him was ill-advised and potentially bad for your career, but it’s not inappropriate to regularly text someone you’re hooking up with. I think he’s a creep and a bad employee (he can’t be getting much work done if he’s got this much time to play Dangerous Liaisons–level mind games) who took advantage of your youth and inexperience and is jerking you around.

It would be a lousy move for him to pull even if he were a guy your age you met at a bar and started sleeping with casually; the fact that he did this while you two were supposed to be working together speaks volumes about his character and professional standards (or lack thereof). To answer your question, then: The best place for you to go from here is out of this weird, boundary-less, incestuous little office and into a sane workplace with a robust HR department.

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Dear Prudence,

I am in the middle of a divorce from my husband of almost 10 years. I had an affair with an out-of-state co-worker toward the end of my marriage and developed feelings for him. In the meantime, my co-worker has been off-and-on about the status of our relationship, and I ended up sleeping with a colleague during a work trip. I admitted to the incident and now my co-worker wants nothing to do with me. I am devastated. What is wrong with me?


Is it terribly trite if I say “the human condition”? That’s not to say that what you’re going through is a universal stage of emotional development, but betrayal and shame and self-loathing are all recognizable recurring themes in human relationships. It’s possible that by the end of your marriage, and again during your relationship with your co-worker, you found the tension of likely heading toward a breakup so unbearable that it came as a relief to do something you knew would end things without ambiguity. That’s also quite possibly not why you did what you did at all! If you’re looking for a quick-and-dirty answer to why you blew up two relationships from the inside in rapid succession—something like “You’re afraid of commitment” or “You’re turning into your father” or “You need to take a nine-week tantric sex course to learn to love yourself”—then I’m afraid I can’t be very helpful.

The upshot is that you get to take all this bewilderment and self-recrimination and put it to good use! Since both of your exes are now just that—exes—you’ve got a lot of time on your hands to get into therapy, take yourself temporarily off the dating market, and figure out what you want your relationships to look like in the future. Pain is an excellent motivator, and I think you have plenty of it to make a good start.

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Dear Prudence,

I have recently come to terms with the fact that I cannot drink responsibly and have started attending AA meetings. I’ve taken it upon myself to apologize to everyone I’ve hurt; some have forgiven me, some have not, and I accept that. My problem is this: My mother is my rock and my biggest supporter, but she thinks I stopped drinking three weeks ago. In fact, it’s only been a week. I want to be honest with her but also don’t want to hurt her. It’s important to me, and to her from what I gather, that I celebrate milestones of sobriety—a week, a month, a year—but I know the timeline won’t add up. Should I come clean or just hope she doesn’t notice the discrepancy when I hit the one-month mark?

—Recently Reformed Alcoholic

There’s a good reason newcomers to AA are encouraged to find a sponsor and work the steps in sequential order. The ninth step reads “Made direct amends to such people wherever possible, except when to do so would injure them or others.” It’s not necessary (or helpful!) to immediately start apologizing to everyone in one’s life—it takes time to clear away the debris of the past, and oftentimes apologies do more for the person apologizing than anyone else. It’s not necessary for you to update your mother on a day-by-day basis about your sobriety. There is, as you likely know, a program available for people like your mother called Al-Anon; she will find support and assistance there. Many alcoholics experience relapse or slipups early in their recovery. The important thing is that you’re sober now and committed to staying that way. If the “anniversary” of your continuous sobriety comes up in conversation with your mother, you can be honest about it with her—and you shouldn’t lie if she asks—but your focus right now should be on finding a sponsor and getting involved in the program, not on making a full confession to your mother.

There’s also a reason that AA members are encouraged to practice their recovery “one day at a time,” and it’s not superstition or pessimism. Worry about your 30-day chip when the day comes, and not before. Congratulations on finding a program that works for you, and best of luck with your continued recovery.

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Dear Prudence,

I’ve been dating a guy for about two months. Everything seemed to be going great. We’d already known one another for a few years, and I thought we knew each other pretty well. The last time I saw him, I spent the night at his home. The next day, I left to get ready for work and didn’t hear from him all day. The day after that, I sent him a link to an article I thought would interest him. He replied, “Crazy.” I agreed and mentioned something else I thought he would find interesting. He didn’t reply.

We haven’t communicated since then. (It’s been a week.) Since I’m the one who sent the last text, I’d say he’s the one ghosting me. But what if he thinks I’m ghosting him? Should I try a quick “Hey, how have you been,” wait it out, or assume this is over?

—Who’s Ghosting Whom?

He does not think you are ghosting him because you are not ghosting him. Nor should you “wait it out” or try to casually start another topic of discussion. It’s one thing to mutually decline to meet up again after a mediocre date or two, but you two have known one another for years, you’ve been dating for two months, and you’ve spent the night at his house—ghosting is neither polite nor standard breakup protocol in this instance. It’s never fun to initiate a conversation that might end in a breakup, but your next move is to say, “I haven’t heard from you since we spent the night together. What’s up?” (You might even decide to call, since texting is proving such an easy medium for him to flake on.) Don’t ask how he’s been because that’s not the question you really want to ask. Be direct, and ask him to be direct with you.

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Dear Prudence,

I work in an administrative capacity for an elected official who has quite a bit of discretion in how they choose to disburse their budget. Recently everyone in the office—except the administrative staff—was given a huge raise. I found out by accident: Someone stupidly asked me a question about the money. I figured out what had happened and someone else in the office confirmed the massive pay increases. This official runs on a platform of reducing income inequality, and their hypocrisy makes me resentful and angry. I’ve started looking for another job.

I’ve stopped all inessential socializing with these co-workers since I can no longer stand to be around them any more than I have to. The problem is that I used to bring in treats for the office almost weekly. I stopped as soon as I found out about the raises. A few people have mentioned missing the cupcakes and have dropped some less-than-subtle hints that they want me to bring them back. I want to yell, “Buy your own damn cupcakes, you can afford them!” Any suggestions for a script to make it clear they’ve enjoyed their last baked good from me?

—Buy Your Own Damn Cupcakes

Regularly bringing in baked goods often results not in increased appreciation but in an increased sense of entitlement—and often an unspoken assumption that the baked-goods provider isn’t as “serious” as the recipients. That’s not fair, of course, but you’re seeing the results of that dynamic in action. You can simply ignore the hints that your co-workers drop about the subject. There’s a certain (socially appropriate) joy in declining to respond when someone says something like, “God, I miss those cupcakes of yours. Hardly seems worth coming in on Fridays anymore. I wonder if I’ll ever get to taste them again?” But if you’re compelled to say something, play it safe: “Oh, I don’t have time anymore. But you’re welcome to bring in baked goods yourself!” Remember that now is not the time to communicate your frustration, subtly or otherwise, to your co-workers. Now is your time to decline to engage, to not worry about whether they’re getting their daily recommended dose of pastry, and to get yours.

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Dear Prudence,

I have a friend who keeps pushing to be invited to events. I’ve known her for several years, but we aren’t that close. My partner considers her a killjoy who psychoanalyzes him too much; others in our group have complained about her mooching. She is a sweet girl with good intentions who simply does not pick up on social cues, and I don’t want to cut her out of my life as I can enjoy her company. However, I also don’t want to get a text every time I choose not to invite her along. She once even told me when my partner had “forgotten” to include her on an email asking a few friends to help us move! How do I politely tell her that it is rude to text me every time she’s not invited to an event I’m hosting, and that it is not always a mistake?

—Pushed Over the Edge

Who is forwarding every email and passing along every invitation to this woman? Either there’s a serious leak in your social circle, or she’s going out of her way to hunt down get-togethers she hasn’t been invited to in order to guilt someone into asking her along. Whatever’s going on here, I’m afraid that there’s no way to be both polite and direct. This woman is being impolite by inviting herself to everything, and the only way to stop her from wearing you down is to say, “It wasn’t a mistake! I’m getting together with Grayabeth and Festerling this Wednesday, and we wanted it to be just the three of us.”

You’ll be tempted to smooth this over by adding, “Let’s get together soon!” or “Some other time!” Resist the urge and continue to invite her out only when you want to see her.

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