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

July 7, 2026 | 8:19 AM
in ABSURDITY, COLUMNS, NEWS
4

By Karen Bergreen and Cynthia Kaplan

Heatwave, thunderstorm, heatwave, etc. We have entered what is commonly referred to as the dog days of summer. We turn, therefore, to an actual dog for advice on surviving the stifling heat. According to Otis, a Welsh terrier and our guest columnist this week, one should lay sideways on a tile floor, exposing as much of your flesh as you can to the surface. When it is no longer cool, move. Your Ruthless Advisors also recommend cool drinks, loose clothing, straw hats, and espadrilles—basically anything that would make you look like you walked out of a Graham Greene novel or a Tennessee Williams play. Personal fans look silly, but no one is looking at you, so do what you want.

Dear Ruthless,

Why are some people so self-congratulatory about their birth plans? The other day at the gym, my workout buddy said his pregnant wife is working with a birth doula and a midwife, and no drugs. As it happens, my wife is also pregnant. Which he knows. So I said she’s going to the hospital and drugs are definitely on the menu. He then lectured me for 20 minutes. I just nodded but I wish I’d spoken up and defended both my wife and our position. What can I say next time I see him?

Signed,

Drug Dad

Dear Drug,

CINDY: People are sanctimonious about all kinds of things. Diet, workouts, books they read, how many documentaries they watch. How to birth your child is just one Ted Talk among many you will receive as a parent. If you’re bothered now, you’ll never make it out alive. My advice is to keep it light. Tell your buddy you and your partner are good with your plan. Both my hospital/drug babies turned out beautifully.

OTIS: I take drugs all the time and, in fact, no one even asks me if I want them. They pry open my jaws and shove their hand down my gullet. Then they hold my snout in a vice-like grip and rub my throat up and down like that does anything. But to the point: Your wife is no fool. I have high blood pressure and without the meds I feel terrible. TERRIBLE.

Dear Ruthless,

I think Taylor Swift having her wedding at Madison Square Garden was completely over the top and tasteless. It must have cost tens of millions and it inconvenienced ordinary New Yorkers on a holiday weekend. Are you telling me there weren’t other options?

Signed,

Backyard  Wedding and Glad

Dear Backyard,

OTIS: I’m glad you’re glad, but when you got married, I’d hazard a guess that no one flew a helicopter overhead that created enough wind to knock down your tent and destroy all the hairdos and scare the dog to death. I’ll bet no one sent a drone to buzz around your guests as they boogied down. I’m thinking no one climbed over your fence and took unflattering pictures and sold them to the NY Post. When you’re the biggest pop star in the world, get back to me. Until then, settle down.

CINDY: I like to consider this in terms of relativity. Enormously wealthy people spend enormous amounts of money. And some of those people also donate enormous sums to charity. Think of MacKenzie Scott (Jeff Bezos’ ex) and Melinda French Gates (Bill Gates’ ex). Over many years of success, Taylor Swift has donated millions to children’s hospitals, cancer research, education, hunger relief, and more. In advance of her wedding, she and Travis donated $26 million to 20 different charities. I know that because I read it on the interweb. If you give the same percentage of your money to charity as Taylor does, then you can do what you want with the rest of it. I’m with Otis. Settle down.

Dear Ruthless,

I have a friend in the hospital recovering from surgery. I know she would love a visit and that other friends of ours have been. I am a true germaphobe and find hospitals incredibly stressful. My husband says I should get over it, mask up, and show up for my friend. I can’t. I haven’t called my friend because she’ll ask when I’m coming and I won’t know what to say.

Signed,

A Mask is Not Enough

Dear A Mask,

OTIS: I live with a man and a woman and I’ll tell you, the man almost never knows what he’s talking about.

CINDY: It is never lame or lazy to tell a friend the truth. (Unless it’s a mean truth. Then keep it to yourself.) Tell her you love her but are truly terrified to visit her and ask for her understanding. Send her her favorite snacks and the latest bestseller. Offer to be the first to visit when she comes home. Whatever you do, don’t choose silence, which can be interpreted in too many ways. In fact, stop reading right now and call her. And then finish reading.

Dear Ruthless,

My neighbor has a dog who barks and lunges and is generally unpleasant. They are good at keeping her on a tight leash around people, and I know they have her working with a trainer. So, I saw the dog out with the trainer and the dog was a perfect angel. Not a lunge or a bark. I asked the trainer if I could say hello and got the go ahead. The dog sat for an ear scratch and seemed perfectly at ease. What gives?

Signed,

Canine Confusion

Dear Canine,

CINDY: Dogs, like children, often behave their best when their parents aren’t around. From my experience, though I’m not naming names, some dogs are aggressive around their owners because they feel protective. They are delightful with a trainer or walker because they don’t really care if some other dog or person decides to eat them or whatever. This kind of protectiveness can be highly annoying, again, speaking generally, but it also can be seen as a kind of love. One can choose to see it that way.

OTIS: Dogs like to mess with your head. Keep you guessing. Don’t get overconfident. The next time you see her she may well be back to her old tricks. At least that’s what I’ve read.

Karen Bergreen and Cynthia Kaplan are the co-creators of The Ruthless Comedy Hour, a comedy variety show for grownups with brains. In its 11th year, it features top stand-up comedians (including this month’s guest columnist Cory Kahaney), musicians and celebrity interviews, and addresses 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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4 Comments
E Lang
E Lang
45 minutes ago

Otis is a keeper

0
Reply
Gofenb
Gofenb
45 minutes ago

I’m with Otis – These billionaires ostentatious display of wealth is disgusting.
Bezoz takes over Venice, Musk buys elections, Swift takes over midtown disrupting thousands of people . Let’s start taking power back. We can start by not buying all the crap they sell. Then vote in some positions to take their I’ll gotten gains back.

0
Reply
Alice
Alice
36 minutes ago

Taylor and Travis also employed many people to make the wedding happen. And their wealthy guests, when. It at the wedding, presumably took Ubers and ate in restaurants and spent money in NYC. The wedding wasn’t my style but I like it when billionaires spend their money and the little people get some of it.

0
Reply
Amy
Amy
28 minutes ago

LOVED hearing from Otis!🥰 (an occasion for deliberate all-caps!)
Possibly my favorite Ruthless column ever!👏😁

0
Reply

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