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

    September 15, 2026 | 8:27 AM
    in ABSURDITY, COLUMNS
    6

    By Cynthia Kaplan and Otis, a Welsh terrier

    Otis.

    In honor of the recent Labor Day holiday, your Ruthless advisor would like to express how surprisingly satisfied she has been with her working partnership with Otis. His frank, succinct responses are a near-perfect (as in, almost Karen-ish) counterpoint to her own almost-helpful verbosity. We here at the Rag knew Otis was intelligent and insightful, but not that he was, in fact, clearly called to do this important work. As such, we believe he has earned his place as a Ruthless advisor. We have made him an excellent offer with significant remuneration and considerable flexibility. When he has conflicts, including travel plans and personal days/weeks, we will invite Upper West Side friends and colleagues to offer their advice, as we have done in the past. Please feel free to leave suggestions for such personages in the comments. Also, may we recommend that while we await Otis’ decision, you might take the opportunity to sit down with your own dogs and try to discern if they, too, have the vocation. We know that you have issues that require answers during our off week, and you may find them closer to home than you think. 

    Dear Ruthless,

    I have a new friend of about six months. We’ve had lunch a bunch of times, played some tennis in Central Park, and we chat on the phone about once a week. We’re long past simple vocal hellos, and now when I see her, I give her a hug. The other day after a morning coffee, she told me she’s actually not a touch-feely person (she used those words) and would rather not have casual physical contact when we meet up. I told her of course, but I’m a little put off. I’m pretty sure I give the appropriate amount of affection for our friendship. Unless I’m wrong about our friendship?

    Signed,

    Lady Who Hugs

    Dear Lady Who,

    CINDY: People have all kinds of preferences. And this includes a category for personal space. It’s lovely that you are a physically affectionate person. But not everyone shows affection the same way, and what is appropriate for one person may not be for another. It is well within your new pal’s rights to set a boundary. In fact, her ability to express this preference speaks to her trust in you and in your growing friendship, unless, that is, you witness her hugging everyone but you. But even then. Some people I hug, some I don’t.

    OTIS: I have long preferred no one touch me unless they have food in their hands. You’d be surprised if I told you how many of us hate having our body squeezed by not only total strangers, but friends and family members. If someone had a camera and could get a picture of the look of panic in our eyes as you envelop us in your presumptuous, self-serving embrace, you might rethink.

    Dear Ruthless,

    My father-in-law acts like he owns the Jewish holidays. He doesn’t even consult with us when planning a seder, Rosh Hashanah dinner, or Yom Kippur breakfast. I have a family, too, and though we’re not as religious, we like to be together sometimes on the actual day, and not some off day. I’ve tried to have a discussion about alternating holidays with him but he still expects me to give in. Help!

    Signed,

    Lesser-in-Law

    Dear Lesser,

    OTIS: I understand your frustration. I’m not religious myself, although, like most unobservant Jews, I enjoy Christmas. You say nothing about what’s in the offing, food-wise, so I’m not sure I can make a recommendation. But I’ll say this: I don’t like a bully, and when I feel bullied, I bark. So maybe bark.

    CINDY: People are like this sometimes. They establish a routine they like and make a unilateral decision that it works for everyone else. I’m curious where your spouse is in this scenario? You do not mention him/her/them, and I’ve always been a fan of making my spouse break the bad news to my in-laws, so you might want to have a conversation. My advice for now is not dissimilar to Otis’. Don’t let yourself be bullied into acquiescence.  Make plans of your own and stick to them. Invite your family wherever you want, whenever you want. And then, after you’ve established your independence, perhaps settle into a routine of every other year or on particular holidays, one of you gets first dibs.

    Dear Ruthless,

    I was at my granddaughter’s first birthday party, and when we began singing happy birthday to her, another child at the party started screaming and crying, so we stopped, assuming the child was hurt or needed attention. As soon as we started singing again, she started screaming again. The mother said, without apology, that her daughter is just upset it’s not her birthday. Then she stood there with her daughter screaming while we finally got through the song. Then the girl screamed some more when her mother wouldn’t let her have cake as a punishment. I wanted to say something, but my son gave me a poke. I’m sorry, but as the kids say, AITA? 

    Signed,

    AITA

    Dear AI, 

    CINDY: The fact is, children have all kinds of nutty ideas about when life is fair or not. And that’s okay, they’re kids. But there is a contract you make as a parent when you take a child to a party, or even take yourself to a party, which is, if one of you misbehaves, you’ll take yourselves off and not ruin everyone else’s good time. You would have been well within your rights to say something. Also, clearly, the mother was taking the opportunity of your grandchild’s birthday party to put her own child through some kind of exposure therapy, which is not the party’s job! Cake for the kid; no cake for the mom.

    OTIS: First of all, for those of you who are unfamiliar with the acronym AITA, it refers to a question: Am I the a-hole? If you are unfamiliar with the expression a-hole, I can’t help you. AITA is often deployed in a situation where you KNOW you aren’t but you feel the tiniest bit unsure, so you offer it up as a kind of laughing defense of yourself. Anyhoo, if I’m being honest, I, myself, am not infrequently TA. In those moments I am picked up like a sack of potatoes and carried away with apologies made on my behalf. This is how it’s done, people. 

    Dear Ruthless,

    I’m on vacation with my partner of twenty years at a beautiful hotel in France. She wants to have sex every night. I do not. I want to have sex our usual once a week and then on the other nights I want to read my book until I fall asleep. But I do feel guilty. Did I mention it’s a very nice hotel?

    Signed,

    Avid Reader

    Dear Avid,

    OTIS: Dear God, how did this get past the editors? Obviously, as I was neutered in my youth, I have absolutely no opinion on this. In fact, it seems insensitive. 

    CINDY: This is a tough one. Who doesn’t love to read on vacation? In all honesty, whether you are married five years or fifty, desire waxes and wanes, and you may not always be in sync. I would recommend a frank discussion with your partner, with much love and even more humor, and find some ways to compromise. As this is a family newspaper, I will not suggest any of those ways. 

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    6 Comments
    Ruthless’ Biggest Fan
    Ruthless’ Biggest Fan
    1 hour ago

    Otis! Can’t believe you are ever the ahole!!! And thnx for the pic! You are adorable as imagined xoxxo

    0
    Reply
    SusiQW
    SusiQW
    1 hour ago

    Otis’ voice is a great new addition to an already enjoyable read! Thanks!

    0
    Reply
    Kkinny
    Kkinny
    1 hour ago

    What a team! Otis definitely an asset. Answers right on the mark.

    0
    Reply
    Bob
    Bob
    45 minutes ago

    I know this is a humorous column, but the concept of casual touching is gone. You touch someone only if you are a very good friend (which is not measured by relationship length but by depth of relationship). If it’s a platonic friendship, there is no need to even think about touching except *maybe* at the death of a family member or if the other person is distraught and would welcomes it.

    0
    Reply
    IZZEE's mom
    IZZEE's mom
    42 minutes ago

    Otis is brilliant.

    0
    Reply
    Jo wase
    Jo wase
    34 minutes ago

    Send the birthday party-pooper to holidays at the in-laws? Read while having sex?
    Lots of possibilities here.

    0
    Reply

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