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

    September 29, 2026 | 8:28 AM
    in ABSURDITY, COLUMNS, NEWS
    0

    By Cynthia Kaplan and Otis, a Welsh terrier

    Fall is officially here. To kick it off, your Ruthless advisor sent Otis to a friend’s house and went off for a week of hiking in the national parks of Utah. Breathtaking, both visually and physiologically. Who knew there were so many humongous rock formations? Centuries of the earth pushing itself up in different ways, creating cool/frightening monoliths of all shapes and sizes, which in turn were eroded by water and wind, revealing canyons and peaks and arches. There were sky-high towers that looked like rocks piled on top of each other but were actually single formations called hoo doos, which to the trained eye all looked like either Bart Simpson or penises. And almost everywhere there were also small caves and holes carved into the rock walls which were made by women from the pioneer era to the current day trying to claw their way out of the valleys so as not be married off to men in their 80s when they were 10 years old. Just a hypothesis.

    Dear Ruthless,

    We had dinner with a client of my husband’s and his wife, whom neither of us had ever met. When we arrived at the restaurant, we were all introduced. The wife, a beautiful woman, I would guess around 40, was wearing a decorative turban, the kind often worn by women going through chemo. When she was ordering she lightly mentioned her taste buds were off, and I asked her if she was in treatment. She then told us, yes, that her diagnosis was recent, over the evening we talked quite a bit about her experience. Later, my husband told me he thought I’d been nosy and intrusive, but I think the wife noticeably relaxed when she realized she didn’t have to hide to make us comfortable. Was I wrong?

    Signed,

    Not Nosy Nellie

    Dear Not,

    CINDY: It is my own lived experience that pretending not to notice someone’s reality, from a cancer diagnosis to a painful loss, is like pretending they don’t exist as a human. We all suffer, and having it acknowledged, even by a stranger, is often appreciated. It sounds like she proffered a subtle invitation to hold space for her and you accepted. People will let you know quickly how personal they want to get, and abiding by the boundaries they set is important. Most people will let you know quickly if they don’t want to have a personal discussion, and abiding by the boundaries they set is very important. I think the key is listening well. Let the person suffering lead. Don’t share your own ills unless asked. Don’t say you know how they feel unless you actually have their exact problem. And don’t be that person who digs a little too excitedly into other people’s troubles. NO ONE LIKES THAT.

    OTIS: You sound like a thoughtful, empathetic person, and I think your husband was clearly not paying attention to how your kind interest was received. I think perhaps he was expressing his own discomfort. That said, I’d like a little more information. What were you all eating? Did anyone have chicken or cheese or both?

    Dear Ruthless,

    In the wake of the latest Trader Joe’s escalator horror, should the city (or state, or country) consider an age limit on who can use an escalator? I feel terrible for the poor woman at the bottom of the pile who was so badly injured and to add insult to injury, had to miss her daughter’s wedding.

    Signed,

    Concerned Shopper

    Dear Concerned,

    OTIS: Cindy and I are deeply upset by the accident, and our thoughts are with those involved, but accidents are caused by people of all ages. If you are nervous, which is understandable, shop somewhere else for now. If you want legislation, consider going after those people who ignore leash laws because they think their dog is better than everyone else’s dog. They’re not.

    CINDY: Yes, Otis and I indeed are sending healing thoughts to the victim of the escalator accident. To the question: No one likes an escalator, especially since You-Know-Which old man rode down one announcing his candidacy/the end of democracy. Maybe if we’d had a law in place in 2016, this nachtmare could have been avoided. Write to your congressperson. Start the process. See how far it goes.

    Dear Ruthless,

    Let me set the scene. During this latest deluge, I returned home from a dinner with a friend, soaked to the skin, and after a cup of hot tea, happily climbed into my warm, dry bed, next to my warm, dry wife. I dozed briefly, waking to remember I hadn’t taken a pill I was supposed to take. I got up, went to the bathroom, opened the door, and in the soft light leaking from the nearby street lamp, I saw, perched on the seat of the toilet, a rat. A rat! I shut the door and said to my wife, “There’s a rat on the toilet.” I got up, and as we opened the door, we heard a splash. It was gone, leaving the seat wet. We complained to the building superintendent, who first tried to gaslight us, claiming it couldn’t have happened, and then asked us to not tell our neighbors. Wouldn’t you tell your neighbors?

    Signed,

    Rats on Four

    Dear Rats,

    CINDY: Oof, sorry. I’m not sure I’d ever use that bathroom again. This is a building issue. I would write to the board, demanding steps be taken. If they respond quickly and effectively, I’d hold off on the mass (hysteria) email. I would, however, dine out on the story every chance I got, and if some of those dinner partners are neighbors, so be it.

    OTIS: I’ve just started a business trapping toilet-hopping rats. It’s a little expensive, but you get what you pay for.

    Dear Ruthless,

    When I host our family and friends for dinner on holidays, I use place cards. I like to mix and match couples and kids so everyone has the opportunity for new conversations and relationships. My mother-in-law consistently changes the seating to suit herself! I don’t want to fight with her in public and I’ve had the discussion in private before. Oy!

    Signed,

    It’s My Party

    Dear It’s,

    OTIS: I don’t sit where I’m told, either.

    CINDY: It IS your party. Explain to your mother-in-law that you love having her over, but the next time she rearranges your placecards, you will take hers and rip it up in front of the crowd, then call her a cab.

    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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