Help! My Sister’s Secret Celebrity Relationship Is Making Our Lives Miserable.

One person whispers into the other's ear, that person has a zipper over their mouth.
Photo illustration by Slate. Photo by cveiv/iStock/Getty Images Plus and DoubleAnti/iStock/Getty Images Plus.

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Dear Prudence,

My sister “Simone” lives abroad and has for almost five years. She has been in a relationship with “Jay” for almost three years, but we only met him last fall. Jay is a public figure, and for career reasons, he must be perceived as being single. He is under a tremendous amount of scrutiny, and from what I understand, Simone has signed several NDAs. Jay’s employers only recently allowed her to disclose his identity to us. Simone adores Jay, and Jay seems to love her right back. I get the impression it’s been very difficult to keep him a secret from our parents, other sisters, and me. At the same time, she’s terrified someone from our family will accidentally disclose Jay’s identity and “ruin everything.”

This has raised some concerns for me about their relationship. I worry about Simone’s identity being revealed. People associated with Jay and others in his position are scrutinized to an intense degree, and others who’ve been found wanting have been intensely bullied. I also don’t know how to calm Simone’s fears that someone in our family will ruin everything. I have been asked to keep Simone and Jay a secret from my own partner. As happy as I want to be for Simone, I wish I was still in the dark. I don’t know how to talk to Simone about any of this, because previous concerns have been dismissed as “you just don’t understand” how things in Jay’s industry work. Should I keep my mouth shut? I’m just worried for Simone.

If you’ve agreed to keep this relationship confidential, even though you wish you hadn’t been told in the first place, then the right thing to do is to keep your mouth shut, at least when it comes to revealing her boyfriend’s identity to anyone else. That doesn’t mean you have to keep your mouth shut all of the time, however; you can tell Simone that you’re not available to hear her concerns about someone else “ruining everything” when you yourself are under considerable strain keeping the secret for her. Her anxiety and distress may be very real on that subject, but that doesn’t mean you’re an appropriate outlet for them.

Regardless of Jay’s professional commitments (and without knowing more, I can’t personally adjudicate how reasonable I think these strictures on his personal life are), if she’s made the decision to share information about him with a small group of people, it’s incumbent on her not to burden those people with repetitive monologues about how they’ll ruin her life if they ever spill the beans. Beyond that, I’d encourage you to be gracious about your sister’s feelings without feeling personally responsible for them. This may be a mistake (or even simply a decision you yourself would not make in her position; no matter how wonderful the guy, there’s got to be a limit on how much that can make up for the downsides of a modern morganatic relationship), but it gets to be hers to make. —Danny M. Lavery

From: “Help! My Sister Is Secretly Dating a Celebrity and Is Terrified People Will Find Out.” (March 2, 2021)

Dear Prudence,

My friend of over 20 years told me, just days ago, that she has breast cancer and has known for six months! She has been through diagnosis, treatment plan, a second opinion, hormone therapy, chemo, and basically a mastectomy. Her outlook is great, and she is now waiting to heal for a month of radiation and then reconstruction. She didn’t tell me because she “needed our friendship to be normal” and “only told a few people.” I feel so stupid and betrayed. I was a pallbearer at her sister’s funeral, for cripes sake! I know this should be about her and her health and healing, but I don’t even want to talk to her. I’m so angry.

I’m glad your friend is OK. And I can imagine how disorienting it must have been to learn about what she’s been dealing with in secret.

But let’s do a thought exercise: Imagine if, six months ago, she’d shared the awful news of the diagnosis with you. How would you have felt? I’m guessing you would have been heartbroken for her and made it a priority to make the process as easy as possible.

What would you have told her? I bet you would have assured her that whatever she was feeling was OK, and that there was no wrong way to deal with this kind of diagnosis.

What would you have wanted? I’m thinking your biggest wish would have been that she would make a full recovery and come out of the process emotionally intact.

Well, we’re there. The situation she’s in now is the best outcome you or any other loved one could have hoped for. She had the experience she wanted, the treatment worked, and it sounds like she has a good prognosis. That’s something to celebrate.

Maybe there’s a conversation to be had about why you didn’t make the list of the few people who were in the loop. When you feel less angry, ask her, and be ready to receive some feedback on how you tend to handle things. You might learn that you can come off as a little overbearing or melodramatic. Or maybe—and I have to admit, the way you’ve written your letter makes me think this might be the case—you have a tendency to make other people’s issues about you. Either way, I hope you don’t stop talking to her. It would be a tragedy if you destroy your friendship over the way she handled her diagnosis. —Jenée Desmond-Harris

From: “Help! My Longtime Friend Didn’t Tell Me She Had Cancer.” (June 12, 2021)

Dear Prudence,

My girlfriend and I have been dating about a year and a half and it is going tremendously; I imagine we will be together a long time to come. I have a considerable amount of tattoos (a full sleeve and several others); I like to get lots of pieces by different artists and it is a huge passion of mine. My girlfriend loves my tattoos. I recently got one from an artist I have not been to before who has a very unusual style. I love it, but my girlfriend does not like it so much—she has never been rude about it, but I just got that vibe from her. Before I got it, I said it was OK for me if this wasn’t her cup of tea, and she tactfully said it wasn’t her favorite but there was no pressure to change it. Since I’ve gotten the tattoo, she has been really positive and said it looks great. I have zero problems with how she handled it—it’s not her thing, but it’s my body and she’s very respectful.

But recently, I got a bonus at work and am planning on getting a full back piece (and advice on the wisdom of spending a bonus on a back tattoo may once have been reasonable, but that ship has sailed). I have a few ideas but the one I am feeling most excited about would be to go back to this artist and get him to do one big piece on my whole back. I know if I brought it up to my girlfriend, she would be totally lovely, and if pushed, say the same thing that it just isn’t her cup of tea—but is it OK to get a HUGE piece of art you know your partner doesn’t like on your WHOLE BACK? She’s going to be the one who does most of the looking at it! I just can’t tell if it would be untactful on one hand, or if I might feel bad about how it looks down the road because I know the person I love (and whose taste I am usually very in line with) doesn’t like it.

Yes, it’s fine to get a tattoo even if your (polite, respectful) partner makes it clear that they prefer most of your other tattoos. That fine-ness exists at scale! It’s fine on part of your back or most of your back, it’s fine if it’s huge or merely quite big. Your girlfriend seems totally able to handle liking some of your tattoos more than others without having a big freakout about your long-term compatibility, and she does not see herself as a co-owner of your back merely because she looks at it more than you do. Get your tattoo; it’s fine! —D.L.

From: “Help! Should I Get a Huge Tattoo I Know My Girlfriend Will Hate?” (April 27, 2021)

Dear Prudence,

I hate my job. I have had many jobs over the years and I’ve never loved any of them, but this current gig is a whole other level of hell. It’s a small company and we’re struggling. I have told my wife that I need to quit, but she won’t support me in that decision. She basically answers me with a very sympathetic, “Wow, that really sucks. Sorry about your luck.” She wants me to stick with it until they fire me or we shut down, so that I can collect unemployment. She is happy for me to find another job, but the last thing I want is another “desperation” job where I have to take whatever I can get for whatever they’re willing to give me. That led me to where I am now.

I have asked my wife for her to return to the full-time workforce. She has been staying at home with our kids since our youngest was born three years ago. She deftly avoids that scenario and offers to help me write my cover letters and sift job postings. The help I need is for her to go back to work so I can quit the job I’m in. She says she doesn’t necessarily want to return to her previous field and isn’t sure exactly what she wants to do. I am on the verge of telling her that she can either support me or leave me. But I fear that she will call my bluff and leave me. What should I do?

If your wife is not willing to go back to full-time work and start singlehandedly financially supporting your family—given that your youngest is only 3 years old and she’s been out of the workforce for years, I don’t think her position is unreasonable—and you don’t want her to leave you, then I don’t think you should offer her an ultimatum along the lines of “support me or leave me.” Generally speaking, it’s a bad idea to offer ultimatums you’re not actually prepared to follow through on.

I can’t agree that your wife is being unsupportive, either! She’s offered you sympathy, encouraged you to look for work elsewhere, volunteered to help make looking for work easier, and is caring for your children full time. You’ve decided that anything short of acceding to your request/demand is unsupportive, but I think there are a few assumptions you’ve made that are worth rechecking. Is there a reason you can’t look for nondesperation jobs while you continue to draw a paycheck at this one? I realize stable, decently paying, enjoyable jobs don’t grow on trees, but I think you should take her up on her offer to help you look for something better, even if that process takes a while. That same process would probably also take her a while, so no matter which one of you were to start looking for work right now, you’re looking at a waiting period. You can also revisit the question of when and in what capacity she might revisit the paid workforce, of course; it’s a reasonable conversation to want to have with her. But I’m not sure your wife, who’s been out of the workforce for years, would be able to find a job that allowed her to support the both of you (plus your children) anytime soon enough for you to be able to quit your own job, so I don’t think it’s the solution to your problem you seem to think it is. —D.L.

From: “Help! My Wife Won’t Let Me Quit My Job.” (Jan. 4, 2021)

I signed up for this political chat line on Reddit. There are thousands of people all talking at the same time, so you have to get in to fit in. This one guy sent me a request so we could chat off-side. I don’t know exactly what it is about him, but he turned me on big time.