Dear Prudence

Help! I Broke Off My Engagement. Now My Friends Keep Setting Me Up With Losers.

I just don’t get it.

Woman crossing her arms and frowning as a hand reaches out toward her holding a rose
Photo illustration by Slate. Images by AaronAmat/iStock/Getty Images Plus and str33tcat/iStock/Getty Images Plus.

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

Dear Prudence,

Why do my friends always seem to set me up with the biggest losers they have lying around their lives? Last year I broke up with my ex. Our wedding was postponed due to COVID, and instead of being disappointed, we were both just so relieved. It obviously wasn’t a good sign and we ended up making that postponement a cancellation. Now I’m back on the market. I’m a catch. Maybe not one to write home about, but I don’t think I’d be thrown back in for the seagulls to pick over. I’m presentable, socially functional, and solvent. Dating apps have turned up a pretty standard ratio of good dates to disasters, with men who are not walking red flags.

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Yet whenever one of my friends tells me they have a guy I have to meet, it’s either someone who brings his mother on the date, a man who genuinely looked me in the eye and said “Patrick Bateman is my idol,” or an active alcoholic (no shame on his problem, addiction issues run in my family too, but an addict with no plans to sober up does not strike me as a good match for anyone I like). I just don’t get it.

Do I seem so desperate that I’ll take any man with a pulse? Do they feel pressured to help me find someone and just don’t have any better options? Have I thrown off table settings by no longer having a guaranteed plus-one? Do they just want someone to fix these disaster zones that are in their lives and I look like the one to do it (I’m not)? I suppose I could ask my friends, but it’s not exactly nice to describe someone in their social circle as an inveterate loser and chronic creep. And it’s not even the men who are the problem. They might all have it in them to make someone happy. I just don’t get what makes my friends, who should know me best, think that someone would be me.

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—Flea Market Dates

Dear Flea Market Dates,

It can be really disorienting meeting the people our friends think we would hit it off with, but it’s not necessarily a referendum on our own worth (or the worth of others). Matchmaking is a skill and, frankly, most people don’t have it. Even if their intentions are good and they know you well, they’re probably not putting that much thought into setting you up. And this isn’t a callous thing; it just means they’re not thinking that deeply about what it takes to make a happy couple. When it comes to friends, we often overlook or forgive things that we wouldn’t in partners. So your friends may think these guys are fun, interesting, what-have-you, but they’re not spending two hours having dinner with them one on one. I don’t think it’s about you or about the guys. Let’s assume that your friends have good intentions but are bad at setting you up. In the future, it’s probably in your best interest to tell them you’re happy being back on the market on your own. No more setups.

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Dear Prudence,

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My mother was an alcoholic, and my father cheated regularly, trading to a younger woman every few years. I always hoped for divorce as a child. Eighteen months ago, my mother died during an attempt at sobriety. My father married “Suzanne” about three months after the funeral.

I have very complicated feelings, but my approach has been to stay polite but distant. I chose to attend the wedding only as a guest, and I call once a month. There’s a selfish aspect—my dad helped me pay living expenses this spring until I graduated and my full-time job started. But I’m unfortunately privy to concrete evidence that he continues to cheat.

I told myself Suzanne knew this was likely going in. This morning, they called to announce that they’re expecting a baby and that Suzanne will be quitting her job to be a stay-at-home mom. Prudie, this is exactly how my mom ended up unable to leave my dad. Should I say something? I know my dad gave my mom more than one STI over the years—should I recommend she get tested for her safety during pregnancy? I don’t want to think about any of this, but this woman is my age and I feel weirdly more sympathetic to her than to my own father.

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—See Something, Say Nothing

Dear See Something, Say Nothing,

The boundary that you’re establishing with your dad and his exploits is a healthy one and I think you should continue to put space between yourself and his life. Your sympathy for Suzanne is understandable, but I fear you’re going to keep getting tangled up in your dad’s choices. Their lives are not your own, and while your dad has, obviously, affected your life in positive and negative ways, his lack of discretion is creating a problem that you shouldn’t have to deal with.

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That said, I think it will put your mind at ease to have an in-person conversation with Suzanne. You don’t have to tell her everything. In fact, it will probably create more drama in your life if you do and your dad might accuse you of trying to poison his relationship. However, the fact that he’s still cheating is different. It’s something that would reasonably prompt you to make sure that Suzanne was aware for her own safety and protection. A conversation that dredges up decades of behavior is going to get muddled, but telling Suzanne information about something that is ongoing in hopes of having her enter this next phase with her eyes open is a kind and practical choice. Be careful, however, that your sympathy for Suzanne doesn’t further drag you into your dad’s life or hers. I’d recommend having one conversation about the current cheating and then keeping your distance.

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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,

I am a 34-year-old who was assigned female at birth, and who is slowly becoming more sure I am nonbinary. I have never felt very feminine and was the traditional “tomboy” growing up. As an adult, I have a male-dominated career and a male-dominated hobby I am heavily in. Despite my chosen pursuits, I’ve always been sure I was not a boy, and although “girl” was always an uncomfortable fit, I learned to make my peace with it in my mid- to late 20s, ironically just as I was becoming more aware there were more than the two options out there.

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My sibling who was assigned male at birth came out as nonbinary a couple of years ago, and it hasn’t gone well with our family. Although nobody is overtly transphobic to them, no family members over 50 will reliably use they/them pronouns (“it’s too hard”) and often confide in me that they don’t “get it.” I never understood society’s obsession with gender—at best it seems strange and at worst oppressive—so I truly can’t understand why some otherwise lovely people can’t wrap their minds around nonbinary people years after the fact. Sure, it’s an adjustment at first, but it seems fairly straightforward to me.

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All of this is complicating my feelings about coming out. I don’t feel gender dysphoria when people use she/her pronouns to refer to me, and I definitely don’t feel a need for any medical transition. I would love for people to stop putting feminine stereotypes on me, but honestly, I think most gendered stereotypes are bad for everyone. I feel torn—half of me feels like a coward for not coming out, and the other half of me feels exhausted by the thought of doing so. I live in a very liberal area and my family reliably votes liberally, but I still know this would be an uphill battle for years, if not indefinitely. Part of me also feels like if I don’t “need” a change (pronouns, surgery, etc.), I should just carry on as is, but the itch in the back of my mind about this just isn’t going away.

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—Please Don’t Ask for My Pronouns

Dear Please Don’t Ask for My Pronouns,

When it comes to coming out or revealing a part of oneself, it can be hard to negotiate the feeling that it’s “not a good time” for others to receive this information. They’re not advanced yet, it will stress them out, etc. There are a million little reasons that pop up. But the only timing that truly matters is your own. You’re not a coward if you don’t come out to your family about being nonbinary for the sake of your own sanity and happiness. If it gets to the point where it’s important enough for you that they know this fact about you, then do it. And don’t entertain complaints of how hard it is to remember. That’s on them. But if telling them is going to rob you of your joy, you have the right to protect yourself. One bright spot here: You have a sibling who understands and will, presumably, walk this journey with you gladly—even if you’re only out to them. If you choose to come out to them, even as someone questioning some of the notions about your gender, it may also help them feel less alone.

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Dear Prudence,

My older sister got married to her husband 12 years ago and moved out of state. They are still living in a one-bedroom apartment with no children. My mom and dad are worried. I’m worried about my sister too, but I already feel like there’s nothing we can do because I myself had an argument with my sister and her husband about vaccines (they are anti-vaccine) and I was the bad guy for caring about their health. My parents are worried because they’ve heard that women who have children in their late 30s may have health issues. They are concerned for their well-being, as am I. Twelve years on and no progress in the family or financial column.

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When my mom asks what’s the holdup, my sister will say, “Oh, well, now is not the right time, I want my kids to go to a good school, my husband is changing jobs, my husband is opening a business, and what if he needs my help.” It’s always something. We feel that they are not open with us. My mom wants to have a talk with them to really try and help, but she’s afraid that they will get offended and things may get heated, which my mom and dad don’t want. Would my mom be overstepping? Should we just mind our own business and let things go?

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—Genuine Concern

Dear Genuine Concern,

Other people’s decisions and finances are always going to be tricky things about which to offer opinions. Add to that opinions about what a person decides to do with her body and you’re really putting yourself in a pickle. Your parents may choose to overstep as they are clearly invested in grandchildren and also the well-being of their child. But you should stay out of it. If there’s nothing raising flags except the fact that they don’t have more room or kids, then you’re best to leave them be. You may also want to have a frank talk with your parents about what kind of help they plan to offer. If it’s financial, do they have the means to significantly change your sister’s prospects? And would a huge influx of cash make a difference with regard to your sister and her husband’s decisions about kids?

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I know that you and your parents are concerned, but it’s likely to feel like you’re putting expectations on your sister that she doesn’t have for herself. It’s even possible that the excuses your sister is giving your family are just attempts to be left alone. She may not want kids at all; she may love her small apartment. Whatever the case, inserting yourself even more is unlikely to help.

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Dear Prudence Uncensored

“Friends can really trim the fat of possible bad encounters you could have from online dates. But, if it’s not working, did you ever try giving your friends feedback on why it wasn’t working?”

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,

My brother and I are having a milestone party soon, and our family has been helpful in both planning and gathering all of the food and stuff for this party. The problem is guests. I only have a few close friends and, in a turn of events, only one of them could show up. I’m not upset by this and I’m excited to hang out with him. I was relying on my brother to bring all the people in anyway.

However, my brother’s friends planned a getaway on the same date as our party and none of them will be able to attend. We found this out kind of early (like a week away from the party date) and I heavily encouraged my brother to go hang out with them. Everyone was cool with moving the party date to accommodate this. But my brother didn’t want to go with them and the party still stands. Now, nobody but my one friend will be there. My parents are pushing us to invite more people because there’s going to be a good amount of food, but I don’t know anybody else enough to invite them to this and apparently it’s too late to change the date. I told my friend about this problem and he said that he didn’t mind, but I don’t want him to feel awkward or obligated. I also don’t want my brother to feel weird at this pretty important thing because he can’t share it with his buddies and now I’m stressing about this! What should I do and how should I feel?

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—Stressed Partygoer

Dear Stressed Partygoer,

While there’s no way to know for sure what your brother is actually feeling, he claims that he doesn’t want to go away with his friends and didn’t take everyone up on moving the date, so you kind of have to take him at his word here. And your friend says he doesn’t mind your party being a small gathering, so while I understand (believe me, I understand) the anxiety about everyone having fun at the party, you can release yourself of some of the obligation you’re feeling. It’s really kind of you to worry like this, but this is also your party and you did the things that you could to make it a good experience for you. You don’t have to feel any particular way, but I encourage you to lean into the idea that this isn’t the event that everyone settled for, this is an event that everyone is choosing. Your brother also chose this option, and ultimately he’s got to be responsible for his own experience. Maybe a chill night at home is what he secretly wants.

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There’s also the matter of the food and the pressure from your parents. It might be helpful to manage everyone’s expectations by changing the description of this event from a party to a dinner party or a game night. You don’t have to throw a rager to have a good time. If your parents can’t pull back on their food orders, you also may want to encourage them to identify a place to donate the extra food in advance (perhaps even before they bring it home). This isn’t what they planned, but again this is your party and your brother’s party, and the goal is to celebrate you in whatever way you want.

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Dear Prudence,

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I was never close to my sister Claudia. She was only a year older than me, and I think because of that, everyone expected us to be best friends and do everything together. Without that expectation, maybe we’d have gotten on better, but instead, we just pushed against it.

If she liked pink, I liked black. When she took up the piano, I went for the soccer team instead. She was my family and I loved her, in that way you love a cousin who you don’t know well. We saw each other a couple of times once we’d left home, but we just had nothing in common. Then six months ago she died. She’d had a heart condition most of her life, but it was still quite sudden in the end.

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The thing I don’t know is how I feel about it. I mean, I don’t know if I’m sad. On a day-to-day basis, I don’t really miss her. Why would I? Even when we lived together, we rarely saw each other every day. Yet, at the same time, I’ll sometimes just be gutted by the sudden thought that I used to be a sister and now I’m not. That I’ll never be able to say “I’m not close to my sister” without putting it in the past tense.

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She wasn’t someone whose company I enjoyed, and I don’t even have regrets about that. We were both OK with our relationship. So why am I crying now over the thought that if I go home for my mom’s birthday this year, I won’t have to make stilted conversation with Claudia? Or that I won’t have to share an inflatable bed with her in the garage while we both try and aggressively fall asleep to avoid small talk?

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I don’t know why I’m writing to you, to be honest. I know the best advice you can give is therapy. It just sounds so stupid to say that I really miss not getting on well with my sister. I guess I wanted to practice.

—Sad Sack

Dear Sad Sack,

The grief that comes from losing a complicated relationship can be complex as well. It might feel like you don’t have the right to feel grief over this or that you’re not grieving in the correct way. But there’s no wrong way to feel grief, even if it’s intermittent and tinged with memories of the chillier aspects of your relationship. While talking through your feelings, with a therapist, a friend, or even perhaps your mother, will surely be helpful, I think there’s something you can do on your own, too.

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The relationship you had with Claudia was unique and not always easy and it may help you to honor that and say goodbye to it in some small way that is yours alone. We have funerals to acknowledge our collective grief and to say goodbye, but it’s also useful—and often necessary—to find a different ceremony or ritual that only belongs to us. People may put up a photo or memento in a special place, they might burn something meaningful, they might write a letter. Whatever it is, it’s unique to them and only meant to serve their healing. See if there’s some way that you can acknowledge how Claudia’s death has affected you and how much you’ll miss not getting along with her. It doesn’t have to be big or even particularly serious if you don’t want it to be. It just has to be something you’re doing for yourself.

Classic Prudie

My wife and I (we’re both women) have been together for 10 years, married just over three. She is the most amazing person I have ever known. I adore her, and I know she loves me based on her actions every day. She is kind, caring, funny, and we cook, take care of our pets, and keep our home as equal partners. The trouble is, I don’t think she’s in love with me anymore, at least not the way I am with her.

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