Dear Prudence

Help! I’m Dating a Famous Person, and I’m Terrified of the Media Finding Out.

I don’t know if I can handle the stress of this relationship.

Two people kiss behind an umbrella.
Photo illustration by Slate. Photo by anyaberkut/iStock/Getty Images Plus.

Dear Prudence is Slate’s advice column. Submit questions here.

Dear Prudence,

For a while, I’ve been dating someone who is somewhat famous. He has no ambition of becoming any more famous than he is, but it is still required due to his job and is a slight burden on him. At first, I thought it would just be a fling, but he’s talking about getting more serious. We’ve kept our relationship mostly private, so I’ve stayed out of the public eye, and I want to keep it that way. I want absolutely no fame. I think it causes only trouble. I’m at a weird place mentally. My close friends keep telling me that I might regret not dating him because we are an amazing fit, and to some extent I’ve internalized that, but here’s the problem: I regret all of the major decisions I have made in the past 10 years.

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These were not poorly thought-out decisions, and they sort of seemed good on paper. But far too slowly, I realized that the situations I had found myself in had become toxic and that these decisions had ruined every area of my life, some of which will be ruined forever. Then, along came this guy, and some of those areas got better. But I’m worried that being in the limelight will end up causing things to be worse by the end. That it will make certain areas of my life, like my career and health, worse. It’s not like I can reverse the decision, either. Once it’s out that I’m his love interest (something the media seems very interested in knowing), I can’t take that back. Any future employers will always see that if they Google me, whether we remain together or not. I’m worried about being threatened or doxxed online, not because I’ve done anything wrong, but because some people are just horrible. So I guess what I’m asking is whether you think I’m overthinking and being unreasonable. Is it idiotic to give up such a good guy for the possibility that, in the end, it would make my life even worse than it was before?

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—Romance Ruined

Dear Romance Ruined,

This question is like a reverse DeuxMoi, the anonymous celebrity gossip account that does the kind of rooting around that you’re so anxious about. Because we live in an era where fans and the casual gossip blog reader feel entitled to any information they want, I don’t think you’re overthinking. But I don’t know that your options are as binary as they’ve been presented. First, let’s talk about decision-making. Without more context, I can’t tell if the decision to be with this minor celebrity would fall into the same category as your previous good but (as you characterized them) ultimately ruinous decisions. But I do know that past patterns aren’t necessarily indicative of future results. And, as you say, aspects of your life got better with him. We also know that fame changes things. Usually for the worse. And you don’t want any more exposure than you already have. So those are the facts at present.

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The thing that’s unclear, however, is whether you have an option of remaining fairly incognito, despite the prying of the gossip sites. For every Notting Hill–style reveal, with the flashing bulbs and the magazine covers, there are dozens of relationships that go unremarked-upon, even involving some of our most famous celebrities. I can’t help but think about Danny Moder, spouse of the star of Notting Hill, Julia Roberts, whose name I know but whom I couldn’t pick out of a lineup. And there are plenty of celebrity-adjacent spouses and plus-ones about whom we know even less. Fame and exposure aren’t as capricious as they may seem, and the famous aren’t always as powerless against prying eyes. Talk to the person you’re dating about your concerns. Ask him if his team (I presume he has a team of publicists or at least agents) can help you stay out of the limelight. Keeping some things in the headlines and other things out of the headlines is their whole job. If he and the people whom he employs take you seriously and can address your concerns, then you’ll know you’re in good hands. If they brush you off, you’re probably best to part ways.

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Dear Prudence,

I’m a gay man in a relationship with my wonderful boyfriend, “Jay”, who is bisexual. We’ve been dating three years and talked about marriage. My problem, however, is either legitimate concern or my own insecurity, and I need advice figuring out which and what to do. Mine and Jay’s dating histories could not be more different. I had one boyfriend before him, my high school sweetheart whom I broke up with aged 19. Our sex life was very “vanilla,” which suits me. I met Jay and became friends when we were 24, by which time he had over a dozen ex-partners and a lot of wild experiences—think sex parties, threesomes, BDSM scene, etc. He was poly, but opted to become monogamous when he started dating me as he knew from our long-standing friendship that I would only be comfy with that. I spent a long time worrying I was too boring for him but thought I had finally gotten over that fear.

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Now two of his exes—a married couple for whom he was their third—have moved to our city. He stayed on great terms with them, which I didn’t mind when “great terms” involved occasional friendly Facebook messages. Now, he is excited to have the chance to regularly meet up with “Nick” and “Sarah” for coffee as friends, and introduced us. Prudie, I hate them. They still have an open marriage, and Sarah seems very flirty with Jay, though he laughs it off as her mannerisms. I know a lot about his relationship with them from how he talked when we were just friends, and I feel sick with jealousy and the fear that he is going to remember how exciting things were with these two and get bored with me. He has always seemed happy with our pretty vanilla sex life, but there are things he did with them that I know I can’t offer him and that I know he found incredibly fun. It’s all I can think about whenever I have to see these people. Would I be out of line to ask him to scale back the friendship with his exes, or am I being insecure? He doesn’t know I feel this way as I have tried hard to be nice to Nick and Sarah, though I have dodged his attempts to invite them into our home. What should I do?

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—Return of the Ex(es)

Dear Return of the Ex(es),

The way you feel is normal, but it’s not fair to ask your boyfriend to stop seeing his friends. He’s developed the emotional maturity needed to maintain these relationships, and by all appearances the contact is healthy for all involved, so asking him to cut it out doesn’t seem right. Still, when an old partner or partners resurface, it’s pretty common for the current partner to compare and to feel they don’t match up. There’s a really delightful episode of the pirate comedy Our Flag Means Death where Will Arnett plays the former pirate bestie of Blackbeard (Taika Waititi), which prompts jealousy in Blackbeard’s current pirate bestie, Stede Bonnet (Rhys Darby). Part of the conceit of the show is the blurry line between platonic and romantic relationships on the high seas, so when Stede starts worrying that he’s not as fun and adventurous as Arnett’s character, it plays like the kind of relationship jealousy you’re feeling.

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What’s true in the show is the same as is true in your life: The adventurous life isn’t always sustainable long-term, and it isn’t always the life you want to lead forever. You and your boyfriend have been together for three years; if he wanted something more thrilling, he’d go back to it. Or he’d have a conversation with you about opening up your relationship. One thing about many people in the poly and BDSM communities is that they have to be good at communicating and getting enthusiastic consent. So take at face value that your boyfriend is living the life that he wants—and that he’ll let you know if at some point he’d like to revisit what that looks like. Nick and Sarah aren’t a threat to you. That doesn’t mean you need to hang out with them. Maybe you genuinely don’t like them. But the only way you’re going to sort your feelings out is if you talk to your boyfriend about your jealousy. Tell him how you’ve been feeling, talk about your anxiety. I suspect being open and honest will defang a lot of your insecurity.

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How to Get Advice From Prudie

Submit your questions anonymously here. (Questions may be edited for publication.) Join the live chat every Monday at noon (and submit your comments) here.

Dear Prudence,

My fiancé and I have been living on separate coasts for over three years. Between the pandemic, my company folding, and my fiancé not finding anything bigger than a shoebox in his area, it didn’t make any sense to sell my house. It does now. My fiancé finally got a town house, my new job is completely remote, and I have had offers left in my mail about the house.

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My problem is that last year, I let my old college friend “Sara” and her young daughter move in with me after she separated from her dirtbag boyfriend. Sara was struggling both financially and emotionally. She couldn’t afford a place of her own and wanted to keep her daughter in the same school. Her only other option was to move back in with her racist parents (her daughter is biracial and her dad died when she was a baby). We have a legal lease, but I wanted Sara to save money to get back on her feet. The agreement was she would pay for the internet and put the rest of the “rent” in a savings account. A studio here costs $1,500 per month. Sara got the entire top floor of my three-bedroom house. She should have at least $20K in savings. Instead, she has $200. All this came out in a fight after I told Sara she needed to start looking for a new place since I was planning on selling “everything” at the end of August (my fiancé has much nicer furniture than me). Her lease ends in July.

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Sara freaked out and asked me how I could “betray” her like this. I told her I gave her over a year to get back on her feet, but she always knew this was temporary. I get to live my own life. Then the truth came toppling out: Sara had taken on outrageous debt to pay off legal fines I didn’t know she owed, get a car note she couldn’t afford, and “help” out some friends (who can’t pay her back). We screamed at each other. I called her a complete moron, and she accused me of wanting her and her daughter to be homeless. I told her that was her fault—she was a piss-poor mother to get her daughter into a position like this. Then she hit me. She didn’t make skin contact, but my glasses went askew. I left and locked myself in my bedroom. Sara kept knocking on my door and crying she was sorry until her daughter came home. We haven’t talked since, other than vague pleasantries.

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My fiancé thinks I need to cut Sara a check for $5K to get them out of the house and maybe pay moving and storage costs. Rent has gone sky-high in our area. Sara will not be able to afford to keep her daughter here even if I give them that. And my friendship to Sara is dead—she lied to me, used me, and hit me. I am still fond of her daughter, and I feel sick about forcing her into the embrace of the family who hates half of what she is. This isn’t my fault, but is it my responsibility? What should I do?

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—No Good Deed

Dear No Good Deed,

OK, put the checkbook away for a quick second here. We’re skidding off the road and we need to pump the brakes. Your compassion, empathy, and generosity toward Sara and her daughter are commendable and humane, but I think they’ve gotten you too entangled in this situation. When helping a friend, it can be really hard not to start back-seat driving their lives—offering advice, orchestrating better systems, giving out armchair therapy. This boundary is fuzzy in a lot of friendships and often that’s fine, but when money gets involved—and even more so when legal agreements get involved—the fuzziness becomes a liability.

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Please don’t take the following as chastisement; I just want to break down the events. So, you and Sara had a legal lease agreement. You then essentially gave her $20,000 in the form of rent forgiveness. You had a plan for what she was going to do with that money, but she wasn’t under any obligation to follow your plan, even though she agreed to it. Now Sara is mad that you are moving on from the property because her fee-free ATM has closed up. While I understand your desire to try to help her daughter avoid an ugly situation, I think if you were to give Sara more money, you’d be getting yourself into a scenario where you have one plan and Sara’s going to do what she wants to do once again. This isn’t your responsibility, and moreover, you may be complicating things by continuing to insert yourself. You’re very emotionally invested in this, and when Sara doesn’t make a good choice, it seems you take it personally. That’s not healthy for either of you.

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Not to mention that she hit you! I can’t believe I’ve gotten three paragraphs in and am only now getting to the assault. I think it speaks to how complex the entanglement is here. You may have legitimate concerns about whether Sara is actually going to vacate the property, but between what she’s said and what she’s done it’s clear that negotiation or paying her off aren’t viable options anymore. She may leave on her own after trying to guilt you, or you may need outside help. Regardless, it’s important that you draw a hard line and hold it. The lease is coming to an end, your friendship is done, and your checkbook should stay closed.

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Dear Prudence,

Eight months ago, my colleague “Andrea” lost her husband. They were married for 20 years and have two children under 18. It’s obviously an awful situation, and Andrea still understandably struggles a lot with her grief. We are fortunate enough to have a great workplace that is very flexible—Andrea took three weeks off paid, and another three weeks unpaid. (Yes, I know I said they’re great, and they are—they are a small company that cannot afford to give someone 1.5 months off paid. They did tell her that her job would always be there for her if she needed more time, and they’ve also been completely supportive of her changes in schedule now that she’s a single parent.)

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A little over two months ago, my cousin suddenly died. She was the same age as me, and we grew up basically as sisters. We were extremely close, and went through a few tough situations in each other’s lives together. I was (and still am) devastated. I took off a week to mourn and am planning on taking another week soon to go with family members to my cousin’s lake house to celebrate her memory. Andrea found out and confronted me, basically saying that I’m a terrible person because I “only” lost my cousin, while she lost her husband/father of her children, and I should be donating my paid time to her, instead of “taking a nice vacation” while her whole life is turned upside-down. I was completely caught off guard and had no idea how to respond, so I said, “Andrea, I’m so sorry you’re going through this. Please know you’ve always had my full support.”

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Well … she took that to mean I was agreeing to give her my vacation time, and I had to stop her, because she literally turned around to walk to our boss’s office to tell them. I said that wasn’t what I meant, I’m sorry she misunderstood. She called me a bitch, and now I’m public enemy No. 1. Around our boss, she dials it down by just not interacting with me, but otherwise, she’s pretty much openly hostile, and a couple of other colleagues have confided that she’s been trash-talking me up and down. I honestly don’t even care about that. They haven’t taken sides, and I don’t expect them to—as long as they’re still civil and neutral toward me at work, I don’t care if they let her vent in private to them. But I cannot keep working with her blatant hostility. I don’t know what to do—I really don’t want to involve our boss (who I do think suspects that something is up), but there’s no way I can talk to Andrea. For clarity: I don’t think Andrea would get in trouble if I reported this; I just don’t want my boss to have to play mediator. So, what’s the solution here?

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—Grief Is a Curious Thing

Dear Grief Is a Curious Thing,

I know you don’t want to involve your boss, but this is kind of your boss’s job. Andrea is responding in an extreme way because of her grief, and you’ve been sympathetic. But she’s also creating a very difficult work environment for you, someone who is also grieving. Your boss has to mediate this. I presume your company is too small to afford an HR manager, which is unfortunate because this is ultimately an HR issue—especially considering a lot of this has to do with time off, which is not your responsibility to negotiate. Part of your boss’s job is to manage the company culture and work through employee disputes. This isn’t something that you can solve on your own, particularly since Andrea has decided to involve other employees. Send it up the chain and let them deal with it. They have a responsibility to you and to the workplace.

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Dear Prudence Uncensored

When you say ‘everyone would say this is a good idea but it was not a good idea,’ it’s hard to offer a new perspective.”

R. Eric Thomas and friends discuss a letter in this week’s Dear Prudence Uncensored—only for Slate Plus members.

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Dear Prudence,

Before the start of COVID, I was running a very successful business in the travel, events, and tourism world. Relief programs and existing contracts helped us stay afloat for the last two years, but it’s becoming very clear that the nature of my industry has changed and the level of income and stability I was enjoying just won’t be possible anymore. And I’m tired of the fear and extra level of responsibility that being self-employed brings.

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I feel really confident applying to decent jobs, and the success of my current work is easy to demonstrate. The problem is that the last “real” job I had—that is, in an office with a boss—ended terribly. I was an executive admin for three years, and my relationship with my boss became quite untenable in the end. He was an insufferable rich guy who had a complaint about every single person he encountered, and spent a truly baffling amount of every day complaining to me that his wife was spoiled, his family was ungrateful for his help, and his friends resented his success. I had to hound him to sign papers and write checks, and he blamed me for our budgetary issues even though how we spent money was never my call, just my job to execute. He gave me work to do that I made clear was outside of my job description and abilities (like bookkeeping and taxes!) and was furious when I made mistakes.

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I gave a month’s notice when I decided I was ready to start my company, and at first, he said he was pleased for me, but his behavior in that last month was incredibly strange. He stopped coming into the office and hired an elderly friend of the family who had not been employed in over 25 years to replace me. They were barely able to operate a computer, and he received my inability to train them as me having one foot out the door and giving up on the transition. At some point he just turned off all my access to our email and software accounts and stopped communicating with me. I never got my last paycheck or was even able to log my last 30 or so hours, so I just never turned in my computer. One of our last conversations was him accusing me of putting personal expenses on my business card (untrue).

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It was a messy and vague ending to the only job I’ve ever had that wasn’t waiting tables. So now, when I need to list my employment history, I can point to five years of hitting goals, working with high-end clients, developing good systems, managing a small staff, following through with projects, and hundreds of lengthy and glowing Google reviews from happy clients. But before that, all I’ve got is a few years grinding my teeth under the supervision of a weird and unprofessional boss who probably wouldn’t give me a good reference. Is there a professional way to speak about this experience? I don’t want to sound bitter or like I’m covering anything up, but for the life of me I can’t figure out how to address it.

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—Will They Overlook It?

Dear Overlook It,

Five years of clearly defined and measurable achievements is very impressive on a résumé, and since it sounds like you’re relatively early in your career, that should be persuasive enough.
Hiring managers know that most people aren’t able to leap right into the dream job, and so the early years of a résumé are often a mixed bag. That said, it sounds like you also had successes with your troublesome boss. And if I’ve learned anything from LinkedIn, it’s to shout wins and never mention anything else. So I imagine, in any interview scenario, you’re going to spend the bulk of your time talking about the experience you gained as an independent business owner. But if they want to know about your office experience, talk about the skills you gained, the benchmarks you hit, and then connect them to the work you did independently. Your job in an interview is to tell a cohesive story that arcs upward. So getting bogged down with your boss’s weirdness or your unhappiness about the job is not going to help move the story forward. Even if they ask something direct like “Did you enjoy this job and this boss?” you can be diplomatic and say, “I learned a lot, but I was eager to branch out and hone my skill set, which I did. I’m glad that I had the foresight and the drive to launch my own business because it gave me the experience and the skills that make me an ideal candidate for this job.”

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Dear Prudence,

My brother is getting married in the fall. His fiancée asked me to be a bridesmaid, which I accepted. She and my brother live across the country, and I have only met her two or three times (once at my own wedding, so there was not an abundance of time for any meaningful communication other than pleasantries). Future sister-in-law seems very laidback about her wedding planning and doesn’t have a ton of expectations of the bridesmaids. She is even going as far as to plan her own bachelorette party, which I think is somewhat unusual but hey, you do you.

As I mentioned, I don’t know my future SIL very well. We have spent maybe a collective 12 hours in each other’s presence. I know asking me to be a bridesmaid was out of obligation. All of the other bridesmaids are her friends from college/postgrad, who I have only met for 30 minutes on a Zoom call. I haven’t heard any plans of a bridal shower, and the bachelorette party is happening on the Thursday before the wedding (which is on a Saturday).

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Here’s the predicament: Future SIL has made a hotel reservation for the night of the bachelorette party, and she wants everyone to share a suite. This means that everyone will be two to a bed, like some kind of big sleepover. I am super uncomfortable with this. One, I am an adult with a salaried job and have no interest in sharing a bed with anyone other than my husband (and even then, sometimes I wish I had the bed to myself!). Even if these were my best friends, I don’t know that I’d want to share a bed unless it was out of utter desperation. I don’t know these women, and while they seem nice enough, I don’t think I would be friends with them had we met under other circumstances. Not to mention that I’m a super light sleeper and get extremely grumpy if I don’t get an uninterrupted night of sleep.

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The suite is only a few hundred dollars split between all of the bridesmaids. My family, husband, and I are flying in from out of town on Thursday morning before the bachelorette party. Family/husband already have hotel reservations made for Thursday, Friday, and Saturday nights. Am I a jerk if I stay with my husband that night and still pay for my portion of the bachelorette suite?

—Too Old for a Slumber Party

Dear Too Old,

Oh, God, absolutely do not feel bad about staying with your husband. Especially if you’re going to be generous enough to pay for the portion of the bachelorette suite. One of the most beautiful things about being an adult vacationing with other adults is the ability to say “I’m not sleeping here.” Once, at a conference, I had to share a bed with a co-worker, and the experience precipitated my immediate departure from corporate life. Our time on Earth is too short for this kind of discomfort. You don’t have to share a bed with a stranger. Hopefully the other members of the party don’t try to make you feel guilty about this. But even if they do, who cares? You can party with them as long as you’d like and then, when it’s time for bed, take your melatonin, your sleep mask, and your pajamas and head straight to your room.

Classic Prudie

I am in my late 20s and have been married to a wonderful guy “Dave” for three years. He and his mother have always had a very close relationship (which I think is great), especially when it comes to their mutual love for a local professional sports team. They have a tradition of going on trips to see their team play away games. This went on even after we began dating, and is continuing now that we are married and have our own home. I think it’s extremely bizarre for a married man in his early 30s to still be taking trips with his mother and sharing a hotel room.

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