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

October 27, 2026 | 7:11 AM
in ABSURDITY, COLUMNS, NEWS
0

By Cynthia Kaplan and Otis, a Welsh terrier

Your Ruthless Advisors love Halloween in New York. We love that children are already walking around in costumes.  We love the local streets closed off from traffic and open to trick or treaters from the neighborhood or any neighborhood. No one asks! We love the families who live on those streets that buy enough candy for a thousand children. We love the shop owners who have bowls of candy on their counters, which usually last a couple weeks into November, for the rest of us. We love apartment-house trick or treating up and down the stairwells, hoping to peek into other people’s apartments, which for some of us is the best part of the holiday after candy corn.

But what your Ruthless Advisors love most about Halloween in New York City is that the vibe is not really restricted to Halloween. On any given day of the year, someone could be walking down the street, sitting in a restaurant, or riding a train in a costume or seemingly outlandish outfit, just flying their own personal flag, and no one bats an eye except in admiration. Hold please for a late breaking opinion: Dog costumes are an affront. 

Dear Ruthless,

The past couple of weeks I’ve noticed a litter of feral kittens near our building. They are adorable. I haven’t seen the mother around at all. Is it okay to just pluck one off the street and keep it? 

Signed,

Cat Shopping

Dear Cat,

CINDY: I suppose so? I presume if they survive the mean streets there’s a chance they will end up in a shelter, so one fewer entering the animal welfare system seems like a good thing. You might ask around and make sure no one in the neighborhood has “outdoor” cats. 

OTIS: Why take just one? And how will you choose? What is this? Sophie’s Choice? I’m just kidding. Do whatever you want. No one cares about feral cats. Although, now having said that, can you pick out one for me? 

Dear Ruthless,

My Upper West Side building has its share of characters, and over the years, one of our long-time doormen and I have shared the occasional innocuous joke about this or that neighbor’s quirk. Recently he has hinted to me that two married neighbors, not married to each other, are meeting up in the building playroom at late hours. I feel like this is too much information and that it is something we should not only not speak of, but certainly not joke about. I’ve encouraged our friendly joshing, and now I want to shut it down without sounding patronizing or judgmental. 

Signed,

Regretful Gossip

Dear Regretful,

OTIS: You pooped where you live, and now you’ve got to clean it up. My advice is that you be very busy for the next few weeks, zipping in and out without stopping for a juicy nugget. It’s hard, I know, passing up a juicy nugget.

CINDY: Doormen are fonts of information and therefore should be the souls..of discretion. I am concerned that you are not the only one on the receiving end of the juicy nugget. You might have a friendly tete a tete with your doorman and explain that perhaps this is more information than you bargained for and you just want to make sure, for everyone’s sake, including his, that he is not sharing it with other neighbors. If the amorous couple are going to be found out, let it be their own fault, not the reason he loses his job.

Dear Ruthless,

My husband just returned from another high school reunion. I’m glad he gets to see friends and reconnect with some of the ones who are lost to time. I don’t go to my reunions very often because those years were pretty meh and I’ve held onto the friendships I care about. Anyway, he came home having made a plan to get together with one of these long lost friends and his wife, who it turns out I knew in college and couldn’t stand. Must I? Must we?

Signed,

No to Dinner

Dear No,

CINDY: There are things my husband does and people he sees on his own. The same goes for me. I think this is healthy. However, if there is a request from one of us to take part in an evening’s festivities, or just an evening, especially with another couple or a group of couples, we put on our friendly face and go. And there are people I disliked at some point that I have totally/mostly changed my mind about. So you might be surprised and have a good time. If not, you can gripe about it all the way home. 

OTIS: I don’t do anything I don’t want to do unless there is something in it for me. Find out what that is or ask outright for something you want in return for the favor. If you are not satisfied, you can “have COVID.” I’ve seen Cindy do it.

CINDY: I had COVID.

OTIS: K. 

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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