Dear Prudence: I’m dating my boss. He wants to tell the company.

Help! My Boss Wants to Tell Work We’re Dating, but I’m the One Who Has to Quit.

Help! My Boss Wants to Tell Work We’re Dating, but I’m the One Who Has to Quit.

Advice on manners and morals.
Oct. 8 2015 6:10 AM

Top-Down Management

My boss wants to tell work we’re dating, but I’m the one who has to quit.

Emily Yoffe.
Emily Yoffe

Photo by Teresa Castracane.

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secretly dating boss.

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Dear Prudence,
I am a single woman in my mid-30s and have worked for a private company for almost a decade. A few months ago, I took on a new role, working for a partner, “Tom,” who is a few years older than I am. He is notoriously volatile but has always been very nice and professional toward me. A few months ago, Tom and I were working late on a project, and he kissed me. I was shocked. Our interactions had always been strictly professional. We are both single, but I never considered him a dating option because he’s brought a series of different glamorous girlfriends to social events. Tom confessed that he’s liked me for years. We have been seeing each other secretly since then. In private, he is gentle, soft-spoken, calm, and fun—a 180 from his rough and short-tempered work personality. He is also extremely wealthy, which brings with it all the benefits you would expect—travel, luxury gifts, fancy restaurants, etc. Tom recently broached the subject of reporting our relationship to work. We think the other partners would want me to switch out of his group if we report, and that would be a bad move for my career. (I would need to switch companies to keep doing the same type of work.) He told that me it’s up to me but that he’d love not to have to see each other in secret anymore. He’s a partial owner so his career won’t be negatively affected. I like Tom. A lot. But all of my friends think something is fishy—they don’t think it’s normal that he has such vastly different work and private personalities, and they also think it’s unprofessional and sketchy that he pursued someone who reports to him. I guess I have similar reservations, but I am having so much fun with this fairy tale relationship that I am afraid to address them. What do you think?

—Confused ... but Having Fun

Dear Confused,
I think that he has nothing to lose, and you have everything. He’s a partial owner, so even if your relationship is seen as bad judgment on his part by his fellow poobahs, you will be the one forced to switch out of your group or even leave the company. (Sure, you can engage an employment attorney if you want to make the case you suffered as a result of sex discrimination. But getting involved in a lawsuit will likely not enhance your life.) Tom clearly likes you a lot. Maybe he’s enjoying spending time with someone who understands his work and is his intellectual equal. But whether this dalliance comes to light or fizzles out is consequential for you in a way it is not for him. You don’t say anything about Tom that makes me think that he’s reporting your relationship because he’s so serious about you; it sounds as if it would just be more convenient for him. My reaction would be different if he had declared his love and said he was done with the revolving cast of arm candy. But I agree with your friends that everything about this is sketchy, and perilous for you: the Jekyll and Hyde personalities, the unbidden kiss while working together, the secrecy, and the consequences of a revelation. I think you need to tell Tom that as much as you’d like to go public, it would be a bad move for you. I also think you should tell him that you two should return to a professional status. Given all the contingencies here, for your own protection, you should think about updating your résumé. 

—Prudie

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Dear Prudie,
I am a woman in my 40s with a brother of similar age. We are both successful people with spouses and children. We are very close. Our parents divorced when we were both little, and both of our parents remarried and have been with their second spouses for decades. We are both close with our dad but have always had problems with our mentally ill mother. I always knew my mother had cheated on my father back when we were young (I was told that caused the divorce). A few weeks ago, a family member revealed that my father is not my brother’s biological father. This was completely shocking news to me. I never once suspected it, and I doubt my brother has either. I asked my father about this, and he admitted that at one point he started to suspect he wasn’t my brother’s father, based on the way my brother resembled the man my mother cheated with. He confronted her and she told him it was true but said not to tell my brother. My father continued to raise my brother as his own, and they have a great relationship. My father says he never plans on telling him, unless a medical reason comes up. I agree that telling my brother will change everything, potentially ruin relationships, and send his world spinning. My father doesn’t see what’s to be gained from that. On the one hand, I agree with him. On the other hand, doesn’t everyone have a basic right to know this information? From what I can tell from Facebook, the real father is still alive, and he has other children.

—Sad Half-Sister

Dear Sad,
I think that shared DNA doesn’t make a family and unshared DNA doesn’t unmake one. This issue comes up so often that when I do live events I often ask for a show of hands from the audience as to whether they’d want to know or not want to know if the man they thought of as Dad was not their biological father. It generally comes out around 50-50, with slightly more people not wanting to know. (I would not want to know.) I truly understand and honor that people are entitled to the truth about themselves. I have long supported open records for adoptees. But cases like your brother’s leave me terribly uneasy. Yes, if your brother were told, he could conceivably collect a more accurate family medical history—assuming it is true that the other man is the father, which would require a DNA test. But that would come at a great cost to his mental health and peace of mind. Shame on the family member for spreading this long-ago gossip, but I think you shouldn’t pass it on to your brother. Your father made the loving decision that he was your brother’s father in every sense. I don’t see the purpose of changing that understanding.

—Prudie

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Dear Prudence,
My wife and I have been married almost 20 years. Like most marriages, it’s been up and down. We have had some big fights recently during which she launched some pretty mean and personal attacks. While I don’t have many friends, I’m not lonely nor have I ever considered myself to be antisocial. During the most recent fight, my wife screamed at me: “How many friends do you have? None. Do you know why? Because you’re an asshole!” I was, and still am, very hurt and disheartened by this. When I tried to talk things out with her a few days later, and told her how much that hurt, she said to stop feeling sorry for myself. Then she said maybe I was hurt because her comments were true. Finally, she asked me if what I wanted in a wife was somebody who makes me feel good about myself. Who doesn’t want that? While I don’t rely on her for validation of my self-worth, I do think it’s important for spouses to be each other’s champion. My wife seems to have a different opinion. What do you think?

—An Unlikable Jerk?

Dear Jerk,
I think that spouses should champion each other and be honest with each other and these two principles should not be in conflict. That’s because your spouse should think you’re great. Not that you’re great every second, and not that you (and your spouse) don’t have qualities that would drive anyone nuts on occasion. Because what’s the point of spending your life paired off with someone you think is an unlikable jerk? A spouse should be able to offer constructive criticism: “The off-color jokes are not going over and you need to reel that in.” “Practice speaking up at meetings. You should show everyone what a creative thinker you are!” But when the critique of one’s spouse runs to, “You should be aware that no one can stand you for good reason, and that includes me,” your marriage has seriously run aground. If you’re interested in the marriage continuing, I think you should suggest going to a counselor so you two can learn how to disagree more constructively, or agree how to gracefully part.

—Prudie

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Dear Prudence,
I try to be thoughtful about the environment, and overall I manage to keep a relatively low carbon footprint. The most challenging decision I have made has been drastically limiting my flying. Luckily, my personal and work travel can be done by train. I tend to think that if I can’t take a train, it’s not worth going. I of course make exceptions for emergencies and transoceanic flights, but I really limit those. The closest member of my family is my brother, who lives a short flight but a long train ride away from me. (The rest of the family is on the other side of the country.) He gets angry with me for not visiting him and my nephews more often. He expects me to jump on a plane for every barbecue, birthday party, and family gathering. I could afford to, but I feel that visiting by train for a longer stay once a year and staying in touch regularly the rest of the time works better for me. How do we resolve this?

—Choo-Choo

Dear Choo,
There are two issues here. One is that your brother is a whiny bully on the issue of visiting. It’s fair of him to want more family in the life of his children, but announcing frequent command performances is ridiculous. Expend some personal CO2 by getting on the phone and explaining to your brother that you adore your nephews, but you have limited travel time and you can’t be there for every occasion, no matter how much fun. However, if the main reason you are sacrificing more contact with your nephews is in order to save the planet, you are chasing a chimera. You know that the plane will leave whether or not you’re on it. Yes, if all planes were empty, they would no longer fly. But I don’t suppose you refuse to drive, charge your phone, or take hot showers. I don’t know if you hope to have children, but if you don’t, and everyone alive makes the same decision, in about 100 years the whole issue of human effect on the environment will be solved. But that would be a miserable way to live—and for the human race to die. So I say if there are occasions for which you would like to see your family, and the only thing that’s stopping you is carbon dioxide, get on the plane and let the hugs from your nephews ease your conscience.

—Prudie

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More Dear Prudence Chat Transcripts

 “You Talkin’ to Me?: In a live chat, Prudie advises a woman who likes to think out loud—and gets flak from her boyfriend for it.”
Swing This Way: In a live chat, Prudie counsels a couple who can hear their neighbors’ active sex life—and wonder if they’d share it.”
Burning Love: In a live chat, Prudie counsels a man driven to lustful extremes by his wife’s habit of going naked when she gets ‘overheated.’”
Involuntary Service: In a live chat, Prudie advises a woman whose boyfriend’s parents are planning a wedding for them against their will.”