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Ruthless Advice for Upper West Siders: All of the Answers With None of the Expertise

June 9, 2026 | 8:15 AM
in ABSURDITY, COLUMNS, NEWS
8

By Karen Bergreen and Cynthia Kaplan

Editor’s note: This month, author, podcaster, and longtime UWSer A.J. Jacobs is filling in for Karen Bergreen, who is on hiatus.

Last month a WSR reader left a comment which read: “Will Wegmans ever open?” Now, we had not discussed Wegmans in that column, nor had there been a question referencing it. And still, a plaintive voice could be heard in the comments wilderness. Will Wegmans ever open? Your Ruthless advisors interpret this to be, perhaps not in intent but in execution, one of the most existential questions a reader has ever asked and we will endeavor to address it. Here goes. Friend, we have no idea and deep research isn’t our thing. But isn’t this the way with so many of life’s important questions? We know what we know, what we don’t know we don’t know, and we have to keep living somehow without Googling ourselves into a coma. We should all embrace our inner Vladimir and Estragon and continue waiting for Wegmans while being resigned to the fact that it is possible Wegmans may never appear. And please keep asking the big questions. We are and aren’t here for them.

Dear Ruthless,

My father is in a nearby residential memory care program. I spend time with him often, take him on small excursions, and manage his care. My sister, who is local, as well, doesn’t visit him and bears none of the responsibility for him, whether speaking with doctors or helping plan for his future. Yet whenever we talk she asks for updates. I’ll be honest, I don’t feel like giving them. I don’t want to fall out with my sister, so what option do I have?

Signed,

Honestly!

Dear Honestly!,

A.J.: You could tell your sister that your dad is okay, but that he’d be better if more of his relatives would come to visit. Try this:  “The doctors say that interaction with loved ones is crucial in preserving the memories our dad has left.” Nudge, hint, wink, raised eyebrow, etc.

CINDY: You clearly work hard caring for your father and certainly don’t deserve to have to carry around the resentment that comes with letting someone off the hook who should be on the hook. I would sit down with your sister and either create a schedule of care that includes her or let her know you will no longer be putting out press releases.

Dear Ruthless,

Is there a kind way to stop my friend from regaling me with endless details of her grandchildren’s accomplishments? I don’t have grandkids yet so I can’t retaliate. I don’t even think I’d want to.

Signed,

Bored Friend

Dear Bored,

CINDY: Oy, not really. Perhaps come to the conversation prepared with topics that interest you and jump in every time she takes a breath. Or perhaps you could ask your friend to wait until your own future grandchildren materialize so you can bore her back. I’m kidding. Friends let friends regale them.

A.J.: Maybe gently inform her that you want to hear more about HER life (and, by implication, less about her grandchildren’s life). Alternatively, you could compare her grandchildren’s accomplishments to historical figures. As in, “She’s 17 and already has a fashion internship? Wow. It’s funny, because I’m reading Joan of Arc’s biography, and that’s the exact same age she took over the French army.” Or you could tell her to shut her piehole. Your call.

Dear Ruthless,

I’m taking a beginner dance class at Steps at the ripe old age of 49. Most of the other beginners are in their twenties. A lot of them seem to know each other. They sit in groups beforehand, stretching, or stand together between floor exercises. They are not exactly excluding me, but I feel a bit like the odd woman and I’m looking to get in. Suggestions?

Signed,

New Tiny Dancer

Dear New Tiny,

CINDY: It’s hard to be the new old girl. First, kudos to you for starting a new hobby, especially one involving leotards and tights. You are so brave. You will, however, need to be a little bit braver. Make the first move. Compliment a dancer on her jetés or ask her where she got her leg warmers. Sometimes people clump up with whoever is familiar because they are shy, too. Also, it’s the Upper West Side. We’re the friendliest.

A.J.: As a fellow not-young-person, I’m impressed! I like Cindy’s idea of asking the young stretchers for advice about leggings—or anything else: shoes or shirts or good Instagram dance accounts to follow. Or maybe you could recommend something to them. You could say that you just watched a great dance-related movie on Netflix – such as the documentary Dancing Across Borders – and ask if anyone else has seen it. Remember that you have lived more of life and are probably a lot more interesting than these youngsters.

Dear Ruthless,

My neighbor rides his bike everywhere, which is commendable. He has a seat for his child, who wears a helmet, also commendable. But my neighbor himself does not wear one. Why???? Can I say something to him? Is it any of my business?

Signed,

Nosy but Concerned

Dear Nosy,

A.J.: There are a couple of ways to go. One is to say, “Hi neighbor! I know that, legally, you are under no obligation to wear a bike helmet. However, from a utilitarian ethics point of view, your decision not to wear a helmet is immoral. You are raising the risk of head injury, which would not only hurt you, but would strain the American healthcare system. So you really should wear a helmet, regardless of your personal preference.”

CINDY: No, it’s not your business and yes, you can say something to him. I love A.J.’s macro approach here. On a micro level, you might gently suggest he’s no good  to his delightfully helmet-clad children if he, himself, is injured.

Dear Ruthless,

My kid is not an artist, but each Friday, when I pick him up from his preschool, his teacher falls all over herself apologizing for the lack of art. She’s a nice woman, and I know she means well, but she is so apologetic that I’m beginning to take it as an insult to my kid. What can I say to put an end to it that won’t make me sound like a jerk?

Signed,

Math Mom

Dear Math,

A.J.: You could always say something along the lines of: “Like the great Buddhist teacher Thich Nhat Hanh, my son believes that living itself is the ultimate art.”

CINDY: Tell her your son does all his art at home and ask if she’d like you to bring her some.

Karen Bergreen and Cynthia Kaplan are the co-creators of The Ruthless Comedy Hour, a comedy variety show for grownups with brains. In its 11th year, it features top stand-up comedians (including this month’s guest columnist Cory Kahaney), musicians and celebrity interviews, and addresses social, political, and local concerns by making brutal fun of them. Bergreen is a veteran stand-up comedian and author of two acclaimed novels. Kaplan tours extensively with her comedy rock band, The Cynthia Kaplan Ordeal, and is the author of two just as acclaimed collections of humorous essays.

A.J. Jacobs is an author, podcaster, journalist, Ted-talker, and human guinea pig who lives on the Upper West Side and only leaves the neighborhood under duress. He has written four New York Times bestsellers, including “The Year of Living Biblically,” that combine memoir, science, humor and a dash of self-help. A.J. is the creator and host of the popular daily podcast “The Puzzler” and he chronicles his UWS life at Substack.com/experimentalliving. 

Got a question in need of ruthless advice? Email Ruthless at info@westsiderag.com.

Read all Ruthless Advice columns here. 

Subscribe to West Side Rag’s FREE email newsletter here. And you can Support the Rag here.

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Please limit comments to 150 words and keep them civil and relevant to the article at hand. Comments are closed after six days. Our primary goal is to create a safe and respectful space where a broad spectrum of voices can be heard. We welcome diverse viewpoints and encourage readers to engage critically with one another’s ideas, but never at the expense of civility. Disagreement is expected—even encouraged—but it must be expressed with care and consideration. Comments that take cheap shots, escalate conflict, or veer into ideological warfare detract from the constructive spirit we aim to cultivate. A detailed statement on comments and WSR policy can be read here.

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8 Comments
Biggest Fan
Biggest Fan
2 days ago

God bless you Ruthless sages for giving context and perspective on the Wegman’s query. I too, have been haunted by it. Sadly, thinking its just one big corporate tease 🙁

2
Reply
Susan
Susan
2 days ago

Always funny with accompanying great advice.

2
Reply
Kkinny
Kkinny
2 days ago

So funny… Thank you!!

2
Reply
Emma
Emma
2 days ago

When friends or acquaintances bore me with grandchildren stories I reply with news about my cat. Also threaten to send them videos. Usually they get the point although some are insulted but it is a satisfying way to end the topic.

Last edited 2 days ago by Emma
1
Reply
Kate C.
Kate C.
2 days ago
Reply to  Emma

Just say, “Girl, I want to hear your accomplishments, not your grandchildren!”.

1
Reply
Peter Le
Peter Le
2 days ago

I noticed my neighbor’s kid riding his bike without a helmet. I had an extra helmet my nephew didn’t wear so I told him, here buddy, this looks great on you!

2
Reply
Linda
Linda
2 days ago

Just perfect, as always!

1
Reply
R McC
R McC
2 hours ago

I’m so glad to see the letter about bike helmets. I see this all the time, parents (almost always the dads) dutifully helmeting their children while not wearing ones themselves. As a dad, I am baffled and enraged by this. What is the thinking!? Good your kid is safe, but you are vital to your kid’s safety in the world, so your head is almost as important to their safety as their own. Please, dads, wear a helmet!! Years ago I was knocked off my bike by a cab. When I saw the deep gash in my helmet and realized that it could have been my skull, I knew I’d never get on a bike without one.

0
Reply

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