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

November 10, 2026 | 8:19 AM
in ABSURDITY, COLUMNS, NEWS
0

 

By Cynthia Kaplan and Otis, a Welsh terrier

As you know, we here at Ruthless Advice strive to be not quite apolitical but certainly not overtly partisan. The fact is that we cannot solve most of those big  problems anyway, so we might as well focus on the ones we can. That said, yay.

Dear Ruthless,

This question is more for Otis, although I’d be interested in Cindy’s take, too. We are part of a morning dog gang in Central Park. The regulars have been meeting for a few years, and there are some newbies and occasionals. Recently, a woman joined the gang with a dog who for some reason hates my dog. She lets her dog off leash and chuckles at its antics and seems to think I’m the one who has to be on the lookout. This is a group I was part of starting, and I’m not leaving. Can something be said? Who should say it? 

Signed,

Mom of a Good Boi

Dear Boi Mom,

CINDY: Ask her respectfully if she could leash her dog when they are joining your dog group. If she doesn’t respond well, you might ask other regulars if they would mention to her that they’ve noticed this dynamic and that up until now, all the other dogs have gotten along fine with yours. You can be understanding — I certainly know what it’s like to have a dog who is picky about his friends — but you have the right to defend your dog.  

OTIS: Do not blame this on the dog. People do that; they shrug and laugh and say, well, you know, dogs. It’s the same with aggressive children. And aggressive adults. If you can’t control your less intelligent charge’s dangerous behavior, apologize and remove them to a safe distance. I can’t believe I have to keep having this conversation.

Dear Ruthless,

I just moved to NYC and am trying to find my people, so to speak. I never quite found them in my old city, and I’m wondering if it’s something I’m doing wrong or there is a new way to go about meeting and making friends that I haven’t heard of.

Signed,

NYC Newbie

Dear NYC,

OTIS: I have often asked myself that very same question. I have particularly struggled to make friends where I live, i.e. in my building’s hallway and on our block. Strangely, anywhere else — further into the park or hiking in the country — I’m pretty much the life of the party. Here’s the thing, you are who you are, and it’s my guess you aren’t doing anything wrong. I’m sure not. My neighbors and I just don’t click. That happens. No one’s fault. It sounds like a move is just what you needed to find your folks.

CINDY: Look, we don’t find our people everywhere we go. My husband has amazing friends from high school and from business school. College? Meh. I have a smattering of lovely friends from different parts of my life, but the people I call “my people” came through my work as a performer. Also, I’m shy, which can be an obstacle. I suggest you start with an activity or two that make you really happy and join groups which engage in those activities. New York City has an abundance of clubs, classes, and non-profits where you might make some new friends. And despite what some may think, this city is one of the friendliest places in the world. Be brave and let us know how it goes!

Dear Ruthless,

The daughter of very close friends is having a wedding with a pot luck dessert. What? I have to bake for someone’s wedding? When did this start happening?

Signed, 

Just Wanna Dance

Dear Just,

CINDY: Humans throughout history have shared the food/financial burden in order to gather together in groups. Weddings, in particular, are a huge expense that not everyone can shoulder. Perhaps some couples just want to step away from the whole wedding industrial complex with its inflated prices and Instagram ready photos. It’s likely no one will know if you brought something or not, so don’t sweat it. But maybe don’t judge it, either. I was invited to a wedding not long ago with the same ask and I enjoyed baking for it, knowing that I was joining the community of people who love and support this couple. And let me tell you, the dessert spread was nuts.

OTIS:  First of all, it’s obvious that you hate love. Second, that’s okay. You do you. Show up without a treat, see how it lands. I can tell you, though, people without treats are not as well-liked as people with them.

Cynthia Kaplan is the co-creator, with Karen Bergreen, of this column and of The Ruthless Comedy Hour, a comedy variety show for grownups with brains. In its 12 years, the Comedy Hour featured top stand-up comedians musicians and celebrity interviews, and addressed 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.

Otis is a 12-year-old Welsh terrier. He is a life-long Upper West Sider. In his neighborhood he is known by many and loved by few. 

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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