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

July 22, 2025 | 8:21 AM
in ABSURDITY, COLUMNS, NEWS
1

By Karen Bergreen and Cynthia Kaplan

West Side Kids is closing! Boo hiss! We know you know this, but we feel it bears repeating. The closing of a beloved neighborhood business always brings a sense of loss, but the idea that in some not-too-distant future (or now) we Upper West Siders will only be buying stuffed animals or Magna Tiles online fills us with existential dread, which no one needs more of these days. Buying a toy in person, for a child — yours or anyone else’s — is an opportunity for joy.  Sure, it’s an opportunity for yelling at your child, but it’s mostly magic –- touching toys we loved ourselves, watching children confirm their passions or discover new ones. And being in a toy store with a child is a life lesson for them. Will they get what they want? Maybe, maybe not. Even worse, will they have to get something for someone else? Horrible! Unfair! But life’s like that. We can’t have everything and sometimes we can’t have anything. But we can look and touch and imagine, and if we’re really lucky and maybe behave ourselves we’ll get a Tickle Me Anti-Semitic Elmo. Google it.

Dear Ruthless,

I’m in a newish relationship that seems to be turning serious. I’ve just met my girlfriend’s family, and we got along great. My girlfriend, who happens to be mixed race, has asked a couple of times when she can meet my family, who are very conservative with a touch of inherited racism, and I don’t want to put her in a position that will be hurtful to her. And I’m worried their attitudes will make her second guess who I am and how I feel about the world. I don’t know how to broach the subject.

Signed,

Embarrassed Slash Worried

Dear Slash,

KAREN: If you think this relationship has legs, you need to be honest with her and see if she can handle it. Your parents are not going to change.

CINDY:  Oof. If you feel your family is a danger to your partner’s well-being, you must act to protect her.  Furthermore, if you think you have a future with this person, despite it seeming a near impossible feat, you might explain to your parents that their involvement with your new family depends on their capacity to grow as humans and leave their prejudices behind.

Dear Ruthless, 

My friend and I are retired and regularly engage in community service. I’ve always been shy, and it helps to go with a pal. Recently, we planned to join the clean up of a small local park and my friend didn’t show, leaving me again to fly uncomfortably solo. She later texted that she was bereft over a recent death in the news. I assumed she must have known this person. Turns out, she did not know this person. I have so many questions, but the biggest is this: What is it with people getting out of stuff because someone they don’t even know died?

Signed,

Am I Insensitive?

Dear Am I,

KAREN: My first instinct is that this seems like an excuse for the lazy. However, there are people out there who are so fragile that any tragic turn of events can trigger a paralyzing response.  Ultimately, it doesn’t matter which of these categories your friend falls into; you are without a helper.  Going forward, try to recruit more team members, knowing that someone will disappoint you.

CINDY: There is a phenomenon you may have noticed, being a retiree, of people who publicly mourn the death of people they hardly know. Whether at funerals or other memorial gatherings, they suck attention like a minivac. There isn’t really anything to do about this behavior except ignore it and find a more reliable pal to volunteer with.

Dear Ruthless

A new neighbor has moved in and I have a huge crush on her. I want us to be friendly neighbors, at the very least, but am behaving like a teenaged idiot, stammering and avoiding eye contact. I also don’t want to be too direct and seem creepy.  Help!

Signed,

Infatuated

Dear Infatuated,

KAREN: I can’t tell if you want to ask the neighbor out or if you want to get a handle on the crush.  If you are trying simply to handle a crush without looking like an idiot, you just need to be as friendly as possible. Do not talk about yourself, that’s where people get into trouble.  Ask her about her day, how it’s going. If you become comfortable with each other, yes, you can invite her to your open house fundraiser for your favorite political candidate or offer to walk her dog in a pinch.  I would stay away from asking her out unless you want to spend eternity with her. It could get ugly in the lobby.

CINDY: GET A HOLD OF YOURSELF! Now, read the room/elevator.  Does she display similar behavior? Is she charming to you or indifferent? Follow her lead and proceed slowly and with caution. Or just blurt it out and be willing to take no thanks for an answer and move on graciously.

 

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Big fan!
Big fan!
4 months ago

If you like their column, you’ll love the Ruthless Comedy Hour live show Tuesday, July 29, 7:30pm @ New York Comedy Club 236 West 78th Street NYC!!!

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