Dear Prudence is Slate’s advice column. For this edition, Luke Winkie, a Slate staff writer, will be filling in as Prudie. Submit questions here. (It’s anonymous!)

Dear Prudence,

For some godforsaken reason, my twin sister has decided that some 50-year-old sad sack, less than a year into his divorce, is her new soulmate. His oldest child is less than seven years apart from us in age. He left his wife of 25 years because he was “afraid of not living.” He just is begging fate to be 20 again.

Our group of friends is very centered on the outdoors. We hike, bike, camp, swim, and sail. My sister’s boyfriend brags about being able to do all these activities, but he can’t. We are left with a whining man-baby who can’t bother to pack sunscreen or extra water, and our entire trip draws to a screeching halt while my sister plays nurse. It is so cringe that most of my friends don’t want to see my sister anymore. I tried to point out to her it’s because she and her boyfriend refused to stop doing activities he couldn’t physically do and then complained that they were left behind. But she wants to play martyr here! She says no one understands their love or their “amazing connection.”

Then she called me to tell me about the trip she went on with his friends, where she tried to “bond” with his kids! Apparently, his friends treated her as an idiot and an infant, while his kids directly told her fuck off. I just started to laugh. It was the worst type of cliché. Did she really, in her heart of hearts, expect to get a warm welcome from them? She still hasn’t warmed up to our stepmother despite our dad getting remarried several years after the divorce (and they’re the same age, at least). She told me I was unsupportive and called me names, so I asked her why she told me to tell her the truth and then expected a lie? This guy wasn’t into her for her “old soul,” he wanted to screw someone young and hot. She hung up on me and blocked me on social media. Our parents are furious with me. They say I pushed my sister back into the arms of a predator and are afraid that she is going to get pregnant to define their “love.”

Honestly,  I am angry with my twin for being so smart and acting so stupid here, and I am tired of cleaning up after her mess. I have been doing it for months. It isn’t like the guy is rich or handsome. He’s just pathetic and desperate. So what now?

—Bad Cliché

Dear Bad Cliché,

I hate to be the bearer of bad news, but I think you screwed up big time here. One of the enduring facts of life is that, occasionally, your friends and relatives are going to date people that suck. This guy certainly seems to fit the bill. I, too, would totally get annoyed at this unmoored Gen Xer nursing his swollen ankles on a hike he begged to go on. But outside of this weird interaction your sister had with his kids and friends—which does seem pretty bad!—I am not detecting anything that would require an immediate intervention. Your diagnosis is spot on. Your twin, indeed, appears to be enmeshed with a mid-life weenie who is attempting to fill a gaping void with the attention he believes he is owed from younger women. But while that’s never a great place to be, it’s also a tale as old as time.

Here’s the thing though: Eventually whatever honeymoon period these two are enjoying will flicker out. At that point, when this man transforms back into the greying divorcée who doesn’t know how to pack for a camping trip, she will begin to complain about him. It appears that has already happened! Your twin beseeched your guidance, but you responded in a way that left her feeling stupid and more dug-in. That’s not the move! When anyone gripes about a partner you hate, you need to tread carefully. Validate her concerns! Be sympathetic about the things she likes about him! But also, be ready to surgically unveil the numerous traits about his character that you find undeserving of her love. Because, remember, it is your sister’s well-being that is important here. There is a time and a place for the I-told-you-so gloating, and it is a group text that she isn’t in.

Please keep questions short (<150 words), and don‘t submit the same question to multiple columns. We are unable to edit or remove questions after publication. Use pseudonyms to maintain anonymity. Your submission may be used in other Slate advice columns and may be edited for publication.

Dear Prudence,

My husband and I have always been on the same page about not wanting kids. My sister is a single mom and recently moved closer to us, so we’ve been spending a lot of time with her and her young son. My husband’s been amazing with him.

He plays with him all the time, gladly takes him places, and seems to genuinely love being with him. It has everyone who knows us, including my parents, constantly telling me what a great dad he’d be and how “we should really have kids.” It’s awful. Seeing my husband happily playing with the kiddo has me questioning whether he is really happy being childless (he insists he is), and every comment cuts at my newfound insecurity about our relationship. I am dreading spending time with friends and family, particularly over the holidays, because I know I will be fending off well-meaning remarks that make me want to lash out. I’d really appreciate a script to shut down the comments before they start or an approach to preventing them altogether, preferably before I punch somebody.

—Mind Your Mouth

Dear Mind Your Mouth,

So here’s the thing. The persona that your husband has embodied—and the same one that is open to you—is that of the “fun uncle,” or “fun aunt,” which are two of the most sacred and beloved characters in American family life. In fact, I’d reckon that it is imperative among us childless millennials to fulfill that role for the good of our collective social hygiene. Show up, rile up the nieces and nephews, have a couple gin and tonics, and head home with the sublime peace of mind that whatever fallout lingers around the corner (bath, bedtime, ugly public meltdowns) is not your responsibility. What I am trying to say here is that there is not a one-to-one correlation between being “good with children” and “wanting children.” If you and your husband have come to a genuine consensus about how you envision the rest of your marriage—and that it won’t include kids—then I seriously don’t think you need to worry that he’s harboring some hidden progenic desires.

Now, onto the more important matter. Your relatives needling you about your stewardship of the family tree is absolutely bad behavior. But any attempt to tamp down those comments in a curt, decisive way—while gathered around the tree on Christmas Eve or whatever—is likely going to leave everyone in the room feeling a little awkward. I am going to guess that those child-rearing remarks are coming from a place of good-faith cluelessness, and while I don’t know the kind of relationship you have with your mother and sister, I’d like to think that the issue could be defanged with more empathy in private. I think something soft but direct—”hey, the way you always tell my husband and me that we’d be great parents makes me feel funny,” perhaps during a walk around the neighborhood—could be a jumping off point for a conversation on a tender subject. That is, of course, if the parties involved understand that it’s OK to not want kids, which they obviously should. 

One last observation: Regardless of your and your husband’s ambivalence towards expanding your own family, I do get the sense that he likes kids more than you. And that’s OK! We all have our tolerance levels. But I’d recommend that you get down on the carpet and try to play with your nieces and nephews, next time you see them. Join in on the fun! It might provide some clarity to the family dynamic, and you might be surprised by how much you enjoy yourself. Become the Fun Aunt, and everything else will fall into place naturally.

We Want to Hear Your Petty Work Drama!

Laura Helmuth and Doree Shafrir want to help you navigate your social dynamics at work. Does your colleague constantly bug you after hours? Has an ill-advised work romance gone awry? Ask us your question here!

Dear Prudence,

I am a 30-year-old man, and I have had the same friend group for a very long time, made up mostly of guys I’ve known since middle school. Over the years, it’s expanded to include their own longtime friends as well. Those of us who are local still hang out regularly on the weekends, and we game together on Discord every week and stay in touch with some of the guys who have moved away through there.  I would say I generally know the basic facts of what’s going on in each guy’s life, but the problem I keep running into is how to help one of them when they’re clearly not doing well. Over the past year, I’ve seen some of them go through it: one of them is getting a bit too into sports online betting, another was laid off and keeps having no luck in finding another job, one of them has alluded to feeling down about being “directionless” in life, etc. But the only way we hear about these things from each other is through passing comments, and we never really go much deeper than that. I want to be there for them, but it’s hard to figure out how. It feels like we’re all facing real-life shit now, and it’s difficult to figure out how to help them or bring up the subject when half the time we’re just preoccupied talking about our shared hobbies instead.

—The Same as It Ever Was

Dear The Same as It Ever Was,

  1. Help! My Husband Constantly Laments the “Failures” of Modern Medicine. Uh, I’m a Doctor.


  2. This Content is Available for Slate Plus members only

    My Husband Is Trying to Teach Our Baby a Really Stupid Lesson

Brother, you are overthinking this. In fact, I would argue that you are already in a prime position to spark up the deeper conversations you want to be having with your friends. There is an old joke about how straight men can only bond with one another when they are relying on some sort of a buffer—be it a football game, a Nintendo Switch 2, or whatever else—to tamp down the tension of, like, eye-contact, or whatever topsy-turvy weight we’ve collectively put on one-on-one hangs. This, unfortunately, is 100 percent true. I have had deep, soul-searching inquiries about, like, the nature of mortality, or the nuances of marriage, or the unforgiving job market, while simultaneously calling a cornerback blitz in EA Sports College Football 25. The hobbies you guys share are the ideal conduit to delve into all of the heavy stuff, in an environment that nonetheless feels pretty chummy and casual. Yes, some of the crises your friends are facing are tough to navigate (in particular, I’d be gentle while approaching a problematic sports-betting habit), but your desire for deeper conversations here can be quickly ameliorated by simply shooting the shit, ideally with some Mario Kart and maybe a six pack of High Lifes coloring in the background.

—Luke

Classic Prudie

My smart, fun, 3-year-old daughter loves her grandparents, my father, and my stepmother. (My mother died over a decade ago.) My stepmother’s two adult children both have dogs they dote on, and their mother showers the dogs with affection and loves to talk about her grandpups. Nothing wrong with that! However, since my daughter was born, my stepmother has frequently made comparisons between my daughter and these dogs.

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