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

July 21, 2026 | 8:30 AM
in ABSURDITY, COLUMNS, NEWS
7

 

By Karen Bergreen and Cynthia Kaplan

Editor’s note: This month, Otis, a Welsh terrier, is filling in for Karen Bergreen, who is on hiatus.

There has been a lot of talk lately, mostly among your Ruthless Advisors on the telephone, about how truly horrible medical portals are. First, it’s nearly impossible to remember which portal which doctor is on, because either they keep switching portals or because the portal has a pompous, generic name like Oracle or Epic or Benchmark, or it has an incomprehensible, unspellable name like PrognoCIS or practicefusion or eClinicalworks. Second, you can be on one portal for more than two places. For example, there’s MyChart at Mt. Sinai and MyChart at Yale New Haven, yet the two MyCharts are separate and don’t talk to each other. What’s the point of that? Third and worst, you can be awaiting difficult news from a scan or blood test, and the results will appear on your portal—sometimes weeks before you are scheduled to talk to your doctor. Maybe it’s the weekend and the doctor’s office is closed. Perhaps you don’t understand what you are reading or worse, you do understand. What ever happened to breaking it to you gently? What fresh hell is this? We here at Ruthless encourage our readers to rant about health care portals in the comments. We actually feel a little better now that we have.

Dear Ruthless,

I’m 83 years old and my husband is 89. We are both, knock on wood, healthy and active. We walk a three-mile loop in the park almost every morning, go out at night, drive, and travel. My husband just asked me to consider having an open marriage. Did I say I’m 83 and he’s 89? It’s a little late, no? I don’t know what to tell the guy.

Signed,

Seriously?

Dear Seriously?

CINDY: I’m wondering, as you seem to be, how much damage he could actually do at this late date. And from the tone of your question, I’m also thinking you are neither threatened nor particularly angry. If that is the case, I’d pack him a lunch, wish him luck, and send him on his way, provided he reports back in detail. However, if you actually feel hurt or insulted, you must tell him so and ask him whether becoming a late-life Lothario is worth the pain he would be inflicting on you. You might also remind him that an open marriage is open on both ends.

OTIS: Very occasionally I hump some cutie-pie, but neither Cindy nor the cutie-pie seem pleased, so I try not to do that. But I do A LOT of sniffing with or without tail wagging, which no one seems to mind. What I’m saying is that maybe your guy just needs to get out and sniff a bit. As I’ve heard Cindy say to her husband: We’re married, not dead. What I think she must mean is they choose not to hump outside the marriage, but the frisson of a little consensual, no-contact sniffing might, you know, keep things lively.

Dear Ruthless,

How can I keep my daughter from letting her 9-year-old twins watch South Park, which is clearly written for older teens and adults?

Signed,

G-Rated Grandma

Dear G-Rated,

CINDY: If your grandkids haven’t started watching it yet, you might recommend to your daughter that they begin with SpongeBob SquarePants, which is the G-rated gateway cartoon to South Park. The truth is, though, my kids watched South Park earlier than many of their peers and they loved it. As did we. Howling with laughter as a family is a core memory, as was (is) my son’s uncanny ability to quote long sequences of the show verbatim. We made it a condition that they never mistook permission to watch the show for permission to speak or behave inappropriately. In my humble opinion, South Park is an honest and often loving look at friendship and community.

OTIS: Step off, Grandma. Exposure to South Park cannot begin too early. It is the truth serum we need in this fraught moment. It insults no one because it spares no one. It is laugh-out-loud funny (well, not for me; I don’t laugh out loud), which makes it an ideal way to introduce your grandchildren to the world of politics, religions, and sociology without scarring them or boring them.

Dear Ruthless,

My wife has accused me of hoarding books in our modest Upper West Side abode. We have bookshelves in every room, and there are a few piles around on tables and chairs, mostly for current reading. I’ll admit it’s a lot. She’s demanding I cull. The problem is twofold. I don’t want to take the time to cull. Also, I don’t want to cull. I love my books, and that was abundantly clear when we met. How do I relay this without sounding inconsiderate?

Signed,

Book Hoarder

Dear Book,

OTIS: I don’t read much. But I do have too many toys in my toy basket, most of them torn and ravaged by time and me, and many, heartbreakingly, sans squeaker. Whether I keep them all or not is pretty much — if not entirely — out of my hands, and I suspect it’s out of yours.

CINDY: I, too, love books. I really don’t understand homes without them, even though I know people use Kindles and Nooks and phones now. There are, in fact, some books you’re going to have to pry from my cold, dead hands. Nevertheless, sigh, it is possible to accumulate more books that your home can hold. I’ve begun a very slow culling of my own, getting rid of books I don’t want to finish, or finished but didn’t like, or feel sure I’ll never crack. I donate them to my building’s shared book room or the local library. On a street near me, people sometimes leave books out on their stoops as an offering to neighbors, which I love. Your wife may have knowingly married you and your books, but, as Otis writes, you might consider which one of those two entities you most don’t want her to get rid of.

Dear Ruthless,

Is it cruel to dress a dog up? I see plenty of charming Instagram accounts where it looks like the dog is perfectly content in its various outfits, but I worry but it seems sort of antithetical to the idea of caring for an animal.

Signed,

Respect the Dog

Dear Respect,

CINDY: Dog videos on Instagram are my jam, and I’ve seen some cute ones with dogs in clothing, but it seems that a lot of the time those dogs in visors or overalls or pajamas look like they want to kill someone. I suppose I can understand a jaunty sweater in the fall or a winter puffer for skinny dogs who shiver in the cold. And I’m willing to give a special dispensation for Halloween. A couple of years ago we had Otis in a headband-like thing around his midsection with a knife handle on one side and the knife blade on the other, which made him look like he’d been stabbed, which some neighbors found apt. Anyhoo, I’m not a fan.

OTIS: You are right to worry about dogs not liking it. I’ve heard cats don’t mind, though.

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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7 Comments
Marcia Epstein
Marcia Epstein
3 hours ago

I hate the portals. I am terrified of looking at results I don’t understand. I think they should be banned.

1
Reply
Robin Rice
Robin Rice
3 hours ago

In addition to those horrible onlike medical portals (which I gave up on), there is this new thing of having an AI voice answer calls to medical offices. AAARRRGGGHHH!

3
Reply
Manhattan parent
Manhattan parent
2 hours ago
Reply to  Robin Rice

Second that. It only wastes your time and adds no value whatsoever.

0
Reply
Ruthless’ Biggest Fan
Ruthless’ Biggest Fan
3 hours ago

Amen and praise South Park! Thanks for this column and Otis’ added wisdom wit and insight. Gotta ask, is he a lefty or righty when he puts pen to page??

1
Reply
Edge of UWS
Edge of UWS
3 hours ago

Not me having a frisson, learning a new word from a dog on a Tuesday. Thanks Otis!

0
Reply
RCP
RCP
1 hour ago

Humping? Sniffing? What does the family pet have to say about this kind of “human” behavior?

As for the 83-year-old posing the question, be open-minded, but tell hubby to be sure to use condoms. Don’t want any STD’s spoiling or soiling the homestead.

1
Reply
Susan
Susan
52 minutes ago

Always a great way to start off a Tuesday.

1
Reply

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