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

March 3, 2026 | 8:09 AM
in ABSURDITY, COLUMNS
15

By Karen Bergreen and Cynthia Kaplan

Editor’s note: This month, comedian Cory Kahaney is filling in for Karen Bergreen, who is on hiatus.

Okay, so spring almost sprung for a few hours on Sunday, and it was delightful. However, we’d like to harken back to a week ago Monday, when our new mayor declared a snow day for the public school children of New York. Whatever you may think of said new mayor, if you had the chance to step out into a city park at any point from dawn to dusk, what you saw was a sea of blissed-out children, teens, parents, and non-parents, sledding, building snowmen, throwing snowballs, and even skiing. It was glorious. As your highly unqualified advisors, we hereby recommend at least one bona fide snow day per year. In fact, we suggest every season have an unexpected day off, like Spring Skip day used to be but not just for high school seniors. And in the fall, Leaf Day, so everyone can enjoy the leaves. 

Dear Ruthless,

My next door neighbor, a very lovely man, has entered hospice. He lived alone in a great one bedroom. We have long wanted to expand our apartment and we would like to approach his relatives. Is it too soon? Should we wait until he passes? We feel like vultures but we’ve been waiting years to expand. 

Signed,

Need an Extra Bedroom

Dear Need,

CORY:  In my view there is etiquette and there’s NYC real estate and you can’t have both! We all have stories that will make you sick to your stomach over lost opportunities from not moving fast enough. The one that still haunts me is a three bedroom, two bath (a true classic 6!), on 106 and Broadway for $750 a month. I “wasn’t sure of the neighborhood.”  Hang on, I have to go get some Tums to finish writing this. Now, is it too soon? Who knows! What if it’s too late? How will you feel living next to the people who beat you to the punch and the hell of their renovation? Call now. Be polite and contrite. Use the phrase “we’d like to make you an all cash offer.” 

CINDY: Cory’s right. New York apartment hunting has its own, very competitive ground rules. But a little finesse goes a long way. A thoughtful note to your neighbor’s family is in order, perhaps sharing some fond memories of enjoying life next door to their loved one. Next, plant yourself behind your door 24/7 and listen for someone picking up the mail or extra socks. Then “happen” to be going out so you can initiate a warm chat, starting with “How are you all holding up?” and ending with “If you decide to sell, we’d love to talk.” Just out of curiosity, Need, where exactly do you live?

Dear Ruthess,

I’ve been out of college for five years and have had a few boyfriends in that time, including my current one, with whom I’m very serious. What they all have in common is that they hate my best college friend. They don’t like how she treats me – she has a history of blowing me off at the last minute or leaving me waiting at a restaurant. I’m tired of defending my friendship with her. How do I get my significant others to make peace with her?

Signed,

Monique in the Middle

Dear Monique,

CORY: Apart from sharing the college experience, I can’t find a single redeeming quality to this woman. No wonder you’re tired of defending your friendship with her, it must be exhausting! I have an old friend that my husband cannot stand. I see this person from time to time because they make me laugh. I don’t expect my husband to be a cheerleader around that friendship. Fortunately, I have enough friends that he enjoys. Truth be told, the friends that my husband likes really do treat me better. That’s how I know he’s the right guy for me. I could be wrong, but your boyfriend just might be a keeper too. 

CINDY: When people stand me up, they’d better have a good reason, like their leg suddenly fell off. Listen, Monique, college doesn’t have to mean forever. Tell your friend to shape up or find yourself a new one. There are lots of lovely, thoughtful, on-time people out there waiting to meet you.

Dear Ruthless,

Before the most recent storm I picked up some groceries for a friend. She is currently housebound with a sprained ankle. I braved the mob at Trader Joe’s to make sure she’d have plenty of what she needs and was happy to do it! But she hasn’t paid me back. I don’t want to seem petty, it’s not a ton of money, but still. How do I ask without sounding like a jerk?

Signed,

Not a Jerk

Dear Not,

CINDY: I do not like presumptuousness. But I don’t mind a little passive aggression, especially when it’s mine. I would send a long, meandering, chatty text, and at the very end write: Oh, I almost forgot. Groceries were $23.59. Venmo is fine. Love ya.

CORY:  Does it help to know, this would drive me just as crazy as it apparently is driving you? Rule of thumb: if it could be an episode of “Curb Your Enthusiasm,” then you probably can’t get away with it without looking like Larry David. And while many of us like watching Larry David pull his mishegos, we know it wouldn’t look good on us. As my old Weight Watchers leader would say, “Call it a vegetable and move on.”  I realize that will only make sense to eleven people who went to my UWS W.W. meeting, but if they’re reading this, hey, I made my goal weight! For fifteen minutes. 

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.

Cory Kahaney has appeared on The Late Show with Stephen Colbert and The Late Show with David Letterman. Other television appearances include CONAN, This Week at the Comedy Cellar, the View and she was a regular on The Late, Late Show with Craig Ferguson. Cory was also a grand finalist on NBC’s Last Comic Standing and a semi finalist on America’s Got Talent, and she has had specials on Comedy Central and HBO. Cory recently presented a Tedx talk called “The Joke that Saved My Life” addressing her journey to escape domestic abuse.

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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15 Comments
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Lydia Sugarman
Lydia Sugarman
1 month ago

Regarding the money owed for groceries, you two are way too nice and oblique.
Just send Sprained Ankle a Venmo for the amount owed. You can follow it up with an email, text, note simply saying, “By the way, I’m going later today if you need anything.”

4
Reply
Ruthless’ Biggest Fan
Ruthless’ Biggest Fan
1 month ago

Another week of sage yet hilarious advice! Many thanks …AND I learned how to spell mishegos!

3
Reply
J R
J R
1 month ago
Reply to  Ruthless’ Biggest Fan

I spell it w/an “a”. Yiddish is flexible. Anyway, that’s my excuse if wrong.

0
Reply
Donald McClean
Donald McClean
1 month ago

I think the distinction is whether or not she asked you to buy groceries — did you do it on your own as a nice gesture?

If I brought food as a gesture, then just like flowers, I wouldn’t ask for a refund.

9
Reply
Carol
Carol
1 month ago

If our neighbors had asked about buying the apartment while my mother-in-law was in hospice, the neighbors might have also needed hospice.

15
Reply
Cindy
Cindy
1 month ago
Reply to  Carol

Note taken!

4
Reply
Steve Raklouk
Steve Raklouk
1 month ago

Do not do that while the neighbor is still alive. More than 30 years ago my wife’s grandmother passed and one of the neighbors the day after the funeral asked about her apartment. The family still tells that story to this day about how rude that neighbor was. Wait. It’s not like they’re going to sell the apartment to someone else so soon.

14
Reply
Cindy
Cindy
1 month ago
Reply to  Steve Raklouk

Again, sage advice.

3
Reply
Marjorie Borell
Marjorie Borell
1 month ago

Just an idea that may help you raise money.: I find the Ruthless Advice Column absolutely hysterical and relatable. What about a tshirt, cap or tote the with the Ruthless Advice logo – text simply “Ruthless Advice” with the tag line ; “All the answers with none of the expertise.”

It could be a big seller! I would buy one.- tote probably.

3
Reply
J R
J R
1 month ago
Reply to  Marjorie Borell

Better patent it b4 the gov’t grabs it. Perfect motto.

2
Reply
Cindy
Cindy
1 month ago
Reply to  Marjorie Borell

Love this.

1
Reply
Susan
Susan
1 month ago

Always great advice with the appropriate amount of NYC sarcasm. Thank you.

2
Reply
J R
J R
1 month ago

My neighbor threw my groceries in w/her delv’y (at my request). Had to txt, call her for 2 wks to hand her cash due. I’m homebound. She actually fought back. We’re both far from rich. For a fee, I’ll divulge our addr.

1
Reply
Joey
Joey
1 month ago

Need an Extra Bedroom, you’re probably too late family already has plans to cash in.

0
Reply
Irena
Irena
30 days ago

There’s a reason many New Yorkers have a bad rep as thoughtless and rude. Now is not the time to be asking about buying, no matter how you do it. The only thing you should be doing is asking how your neighbor in hospice is doing, whether you can help his/her family during this period. Kindness is what they need. Not greedy neighbors. FYI: They may already have contacted someone about selling the apartment or even have someone in mind. I don’t care how much you want and waited for that apartment, if you didn’t make that clear to your neighbor long before they entered hospice, it is beyond inconsiderate to bring it up now. Yes, I’m a New Yorker of almost 60 years and I get how much an apartment like that can mean but people’s feelings are involved here. I am reminded of a story told to me by a friend of something similar in her building. The neighbor with the desired apartment was going through a tough time and two different neighbors approached…neither one offered any help or assistance or even acknowledged the challenges the neighbor was facing. It was clear to anyone who knew her even a bit (or was aware of building gossip via staff) that she might be leaving the building sooner than later. When it came time to sell, she sold to a family friend who did not live in the building. The vultures who had asked about buying were furious (As if she owed THEM the apartment.) She told them that had they not been so uncaring and callous, she would have approached them to buy but at a time when she needed support, they thought only of themselves and offered no words or assistance of any kind. So unless you plan to offer way above market value so the person selling so they won’t want to say no, if you’ve been interacting only to make your personal desires known…don’t be surprised if you are shut out. If you’re lucky, the family of this person, when/if they pass, won’t hold your callous indifference to timing requests against you and let you bid to buy. Then again, families have been known to deliberately sell to someone who doesn’t live in the building to deliberately thwart a neighbor whose only concern was getting the space. You reap what you sow sometimes.

5
Reply

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