Dear Prudence: I’m falling in love with my boss.

Help! My Boss Gave Me That “Look,” and Now I’m Falling in Love With Her.

Help! My Boss Gave Me That “Look,” and Now I’m Falling in Love With Her.

Advice on manners and morals.
Jan. 28 2016 6:00 AM

Come to My Window Office

My boss gave me that “look,” and now I’m falling in love with her.

Mallory Ortberg
Mallory Ortberg.

Photo by Sam Breach

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woman looking lonely.

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Dear Prudence,
I’m a personal assistant to a highly accomplished woman a few years older than me whom I admire and respect a great deal. I’ve worked with her for five years, and we have a close professional relationship. This weekend, we were together late one night when she confided in me how lonely she was; the long hours we work make it difficult for her to maintain a relationship, and she has few friends nearby. Then she told me how good it was to have someone she could confide in and how grateful she was that she could speak to me in confidence. She gave me a look that under any other circumstance I would have taken as an invitation to kiss her, but she’s my superior, so I didn’t. Now I’m not sure what to do. I think I’ve developed feelings for my boss and I don’t know how to proceed. I’d appreciate your input, even if it’s just to tell me I’m being ridiculous and let it go.

—In Love With the Boss

I don’t think you’re being ridiculous, but I wish very much I had an idea of what the look she gave you was. It is possible to mistake a “Thank God I’ve got a friend like you” face for a “Kiss me, dammit!” face. One can’t expect every manager to act like a complete automaton with her long-term employees, but she did put an arguably inappropriate amount of emotional pressure on you by sharing her loneliness in such detail. What you do next will depend on the strength of your feelings. (It should go without saying that you should not kiss your boss as long as she remains your boss, no matter what.) If you think in good time your feelings will fade—based on what you’ve told me, she clearly considers you a friend but I’m not at all sure she was making a pass—then let yourself go a bit swoony and wait for it to lift, privately. If you think you’re in danger of falling in deep, you owe it to yourself to find a new job. The degradation of fetching coffee and updating the schedule for someone you’re in silent, agonizing love with is good material for a period drama, but a bridge entirely too far for mere mortals.

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Dear Prudence,
My mother is the only person in my family who knows I’m gay. She has cautioned me against telling my brother, saying that she doesn’t think he will be very accepting. This was news to me; my brother and I were not close growing up and have only started to recently reconnect as adults. I would like to tell him, but my mom’s warning has me worried. If my brother reacts poorly, it could jeopardize the relationship I have with my baby niece. I’ve thought about testing the waters by telling him about a friend of ours who has come out in the last year, in order to see what his reaction is. This friend has given me her blessing to do this. But my mother is against this, saying it’s cowardly to rely on my friend as a crutch. My mom is underestimating the level of stress this secret has placed on my shoulders, but is she right about this? Obviously it would be wrong if my friend hadn’t given me express permission.

There’s nothing wrong with wanting to test the waters, but surely you don’t plan on staying closeted to your brother for the rest of your life just in case he might be the kind of person who bars you from seeing his child. It’s not uncommon for a parent to try to control the coming-out narrative if they’re the first person in the family to know. I can’t say with certainty, but it’s possible that by delaying and discouraging you from coming out to the rest of your family, she is hoping that the “issue” might vanish on its own, or you might change your mind about your sexuality. Her reasons against your trying to see if he’s as homophobic as she says he is by mentioning another gay person don’t make much sense. If he’s never said anything to suggest he’s a homophobic person, I think your mother is throwing up unnecessary obstructions.

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Dear Prudence,
About two or three times a year, I get crippling period pain where I can’t stand up or think straight. I’ve had to leave work early a few times and colleagues helped me out of the building. I tell them I have vertigo or I’m light-headed. Is it OK to be honest? I’m not ashamed, it’s more that I don’t want my male colleagues to be embarrassed.

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—Out of Commission

It’s OK to be honest, but a better choice would be taking a sick day. If you can’t walk out of a building under your own power, whatever the cause, you have no business forcing yourself to go to work. And if you haven’t already, please go to a doctor to discuss the possibility of being treated for endometriosis, a condition that causes debilitating pain during menstruation.

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Dear Prudence,
I recently moved back across the country with my young daughter, where I hoped to spend more time with old friends. They are nice people but busy with their own lives, and I’ve only seen them very occasionally. As a working single mom, I don’t have too much time to make new friends—I’ve met some interesting people, but on the whole I’m pretty lonely. I try to focus on what I have control over to improve my life, and I know my old friends are not responsible for my happiness. But I get in a negative thought loop about how my life could be different if these friends had welcomed me back into their lives more. Can you give me a little objective perspective that could help me kick the negative thinking habit?

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—Out of Touch

You’re hurt, but it’s not anyone’s fault. Because of that, what you describe is a particularly difficult kind of unhappiness. You sound incredibly self-aware and thoughtful, which I can imagine makes loneliness uniquely painful. I can offer you the usual panaceas—try inviting your friends over to your house more often, or try making friends with other working mothers who share your tightly packed schedule, etc.—but that’s not what you’re asking. As long as you think of negative thoughts as something to avoid or diminish, they’ll continue to overwhelm you.

Address your loneliness the next time you find yourself dwelling on these thoughts. Interrogate it gently. “I’m lonely, but if only my old friends would have me over more, I’d have an entirely different life” is a predictive statement, and false. “I’m lonely, and I miss my old friends” is a simpler, true one. “I’m lonely, I’m always going to feel this way, and I’ve missed my chance to form meaningful relationships with other adults” is a false statement. “I’m lonely, and I’m afraid of not getting help with my loneliness” is a true one. Reducing your fears to their essential components can help take some of the power away from them. “I’m lonely” is a complete sentence; you only run into trouble when you add hypotheticals and sweeping pronouncements to it.

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Dear Prudence,
What happens if you are in love with three people? I am crazy in love with my spouse, in love with an ex whose cheating ended our relationship, and I am in love with my ex’s son, whom I dated just before meeting my spouse. It is really hard because my spouse is so wonderful I can’t believe it sometimes, but the other two men keep hanging in there, telling me they are going to get me back. There is only one of me and three of them. I do not want to risk losing my spouse, but I can’t stop loving the other two. I do not want to lose them either, as they have been treasured friends to me.

—Pulled in Every Direction

What happens? Generally something bad. It may occasionally be possible to hold the three in balance, particularly if you were part of an extraordinarily evolved open relationship, but I don’t see that being your situation. And an open relationship is one thing; welcoming in a family set of exes is another. Your exes are also actively (and I assume independently) trying to end your marriage. You’re all at cross purposes. If you get what you want—to stay in your marriage and remain close friends with the two men still in love with you—they lose. If either of them gets what they want and you leave your husband for them, your husband loses. Trying to play all three of them against each other might just end your marriage, in which case you lose. One can’t have everything; it may be time to start loving those friends from a distance.

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Dear Prudence,
I have been in a relationship with a great guy for about seven years. We got engaged a year ago and this morning he decided he didn’t want to get legally married—something about not wanting the state to have a say in his relationship, and I think he’s worried about potentially having to split assets in the case of a divorce (he earns more than I do). I’m not quite sure how I should take this or what I should do.

—Cold Feet

If this were just about anti-statism, I think you two would have had a conversation about government-sanctioned marriage before you got engaged. If it were about protecting his assets, he would have brought up the possibility of a prenup. This sounds like he wants out of your engagement and is being a bit of a coward about it by hiding behind a vague anti-government sentiment. Ask him what he really wants, and decide if it’s at all compatible with what you want. If he dithers and offers a lot of hazy excuses about “the man,” I think you have your answer.

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Dear Prudence,
I have some serious health problems and the painkillers that help me go about my day make me violently nauseous. I’ve tried tons of different medications each with worse side effects. I’ve finally found relief with medical marijuana. I can play with my kids again! I can go out to eat or take a walk! The world has expanded beyond my house once more. My landlord recently called me to inform me my neighbor had complained about the smell of marijuana coming from my apartment and since my lease states the building is nonsmoking, I could face eviction. The problem is, I don’t smoke or even vaporize it. I buy premade edibles. There is no smell. The only way my neighbor could know about any of it is if he opened my mail or went through my trash. I have no idea what to do. Do I try to explain? File a police report? If I’m evicted, my kids and I would be homeless.

—Smoke but No Fire

Your landlord received a complaint about your apartment and feels obligated to respond, but I don’t think you are in any danger of losing your home. Ask the landlord for specific times of the supposed smoke smell and explain that these concerns are unfounded, as you do not smoke marijuana. (Whether you occasionally consume edibles isn’t the point; you’re being accused of smoking marijuana in your home, which you don’t.) It’s likelier that the smoke is coming from a different tenant and your neighbor is mistaken than that your neighbor has been going through your trash and is trying to sabotage you. Get in touch with your local rent board and learn your legal rights as a tenant. You can’t be evicted on the basis of a single unfounded accusation, and any given notice would provide you time to fight it. Don’t file a police report. Keep your edibles in a sealed container in the back of your fridge and stick to refuting the accusation.

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Dear Prudence,
My husband and I and are moving into a larger home with our children. We’d like a home with an in-law suite so his sixtysomething parents could live with us. We both adore his lovely mother (who is kind, hardworking, and practical) but are exasperated by his lazy, critical, spendthrift, alcoholic father. She has serious health problems and will likely die within 10 years, so we want her to have maximum access to her only grandchildren. Perversely, her husband is in good health and will likely live into his 90s based on family history. We don’t want to support him and suffer his insults for 30 years, especially once she is gone. Is there any way to set up a co-living situation just as long as she is alive?

No. There is no way to invite someone to live with you on the condition that her husband must pack up upon her demise. While you can’t predict with certainty how long either of them is going to live, you’re setting yourself up for a nightmare if you invite your father-in-law to live with you. Buy your house and invite your mother-in-law over to dandle the grandkids on her knees as much as she likes, but don’t ask them to move in with you.

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