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

May 12, 2026 | 5:52 AM
in ABSURDITY, COLUMNS, NEWS
0

By Karen Bergreen and Cynthia Kaplan

Editor’s note: This month, actor, comedian and longtime UWSer Brad Zimmerman is filling in for Karen Bergreen, who is on hiatus.

Readers will be pleased to know that your Ruthless Advisors eschewed this year’s Met Gala. Despite the gorgeous engraved invitation, which arrived in a glass and faux brass jewelry box ($29.50 on Amazon), we were not tempted to pull our coordinated Andrew Wyeth Christina’s World costumes from storage—Karen as Christina, Cindy as the grassy expanse between Christina and the house, and Brad as a dead crow from a different painting. We rather stood on principle with our friends Meryl and Zendaya. The five of us spent a very pleasant evening eating Junior Mints and Skinny Pop and rewatching the hot-priest episodes of Fleabag.

Dear Ruthless,

My parent’s apartment has been sold, and we are selling some of the furniture. The money from both will go towards my mother’s care at a nearby rest home. A friend of my mother’s told us more than once she wanted the dining room table and chairs, a beautiful old set, and we settled on a price. Another of my mother’s friends made an offer on the dining room set, but we told her it was spoken for. It’s now a week from closing, we have to clear the apartment, and the first friend just called to say she doesn’t want the set anymore. How should I respond? I mean…

Signed,

Just Plain Annoyed

Dear Just,

CINDY: My guess is your mom’s friend, precisely because she is your mom’s friend, assumed you would say okay and then let her off the hook. I say make her squirm until she cracks. You should be honest and tell her that you put off other buyers for her, you will now have to give it away just to get it out of the apartment, and your mother was counting on those funds.

BRAD: You have a few choices here. You might try to make her feel guilty. You might try lowering the price. Avoid raising your voice. That’s a deal breaker. If she doesn’t bite then call the other person who made the offer and simply tell them that the dining table is now available and hope there is still interest. Short of that you could just give it away. Put it outside by the curb with a little sign that says, “For sale. $500 or whatever you got.”

Dear Ruthless,

I signed up my daughter for a daily after-school dance intensive at a local dance studio. The mom of a girl in her class recently asked where my daughter studies dance. This girl is the leader of a group of girls at school that is distinctly not nice to my daughter. I don’t know what to tell the mom.

Signed,

Dance Mom

Dear Dance,

BRAD: This is delicate. Before calling the mother, ask your daughter if she is okay with this other girl taking dance class with her. After all, we are not talking about other girls, just the one. If she is not, you have to call the mother of this girl. But what to say? You don’t want to do it in a way that suggests her daughter is a bad person. Share your daughter’s sentiments with the mother in such a way that she might actually volunteer to find another class for her daughter. Just be really honest and sweet and hope the mother herself is not a bad person.

CINDY: I purposely didn’t tell people where we were sending our kids to camp so they could get a break from both their school friends and frenemies. It’s good to show your kids that there are other worlds besides school where they can make new friends and even be a little new themselves. And please do everything you can to stop this bully from following your kid around. Maybe explain that your daughter needs a space apart from school. Or else run away any time you see the mom coming.

Dear Ruthless,

I’m a waiter in a neighborhood restaurant where lots of people are regulars. There is one family that comes in every week for brunch, sits in my station for an hour and a half, and doesn’t tip. At all. I give great service, if I may say so. Is there any way to approach them about it?

Signed,

Waiting

Dear Waiting,

CINDY: Are they French? If not, they need to pony up. I would take this to your manager and request to either add an included tip to the bill or have the manager approach the table having noted the lack of tip and let the family know tipping a good waiter not only a nice thing to do but tips are a large part of a waiter’s take home pay.

BRAD: Some restaurants tell their employees that they are not to approach the customers as it relates to gratuities. In which case there is nothing you can do short of writing on the check something like, “Hey, don’t forget my tip!” Walk over to the table with the check in hand and say to them, “Was everything all right?” If they say yes, it opens the door a little bit and you can add, “I don’t know if you are aware of this but it is customary to leave a gratuity for the waiter if the service was up to par.” If they feign ignorance and say to you, “Oh we didn’t know. How much should we leave?” Then you can say, “Just triple the tax.”.

Dear Ruthless,

I slept with my co-worker after an office party.

Signed,

Slept with Co-Worker

Dear Slept,

BRAD: You’re in trouble. It’s a Shakespearean dilemma, especially if you are married: To tell my spouse or not to tell my spouse? First thing to do is ask yourself how was the sex. If the sex was really good, don’t tell her. And if the sex was lousy, there is no need to. If you tell her, expect a certain period of time in which you are persona non grata. How long it takes to recover from your indiscretion probably hinges on how evolved she is as a person. Or it may hinge on how much she loves you. If she loves you deeply, I wouldn’t want to be in your shoes.

CINDY: Married or not, you must also consider what to say or not say to your co-worker. Kindness, humor, and respect for privacy should lead the way. As it stands now, I give you an A+ for asking a question without asking a question. It reflects a level of self-aware resignation that makes me proud to share the moniker “Upper West Sider” with you.

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.

Brad Zimmerman is an actor, comedian, and longtime Upper Westsider. As a comedian he has worked with some of the legends of comedy, such as George Carlin and Joan Rivers. He has headlined all over the country in casinos, theaters, and clubs. His hit one man show “My Son the Waiter, a Jewish Tragedy” played off-Broadway for well over a year, and as an actor he played Johnny Sack’s lawyer on the award-winning HBO show “The Sopranos.”

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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