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

By Karen Bergreen and Cynthia Kaplan

Editor’s note: This month, Broadway lyricist Amanda Green is filling in for Karen Bergreen, who is on hiatus.

We at Ruthless Advice sometimes have questions that even we cannot answer. Here’s one we’re currently grappling with: What the heck happened to the traffic lights in Central Park? Why are they still covered in burlap? Are pedestrians and dogs never to cross the park road safely again? It was bad enough when bikers blew through the red lights. Now they stop for nothing and no one. At the 86th Street crossing, there are words newly painted on the roadway demanding bikers to stop for “Ped.” Peds? PEDS? They can’t even bother to write out the word pedestrians? Peds could be any number of things and some of them are not good and we wouldn’t WANT you to stop for them. Your Ruthless Advisors have not called 311 because we are too busy answering your questions. We were hoping one of you would take it upon yourselves to return the favor. No pressure, though.

Dear Ruthless,

My daughter is about to walk out the door to a party wearing a bra under a denim vest and it looks like she forgot her shirt. It’s all bra. Is this a thing now? Not a little peek-a-boo of bra strap or cup lace, but full on bra in your face. Is there some way to let her know this is a Fashion Don’t? Is it a Fashion Don’t?

Signed,

Fashion Shouldn’t

Dear Shouldn’t,

AMANDA: Don’t worry your pretty little head if it’s a do or a don’t! And don’t let her know what you think of her “look” unless she asks. Remember what you wore at her age? I do—and am still embarrassed—but it was my time to experiment and express myself and/or be a sheep and try to fit in by wearing what everyone else wore, like Spandex pants, stilettos and oversized tuxedo jackets. With only a bra underneath, come to think of it. Give her a kiss, tell her to have fun and slip an AirTag into her pocket so you can follow her every move.

CINDY: There are Fashion Don’ts and there are Fashion DON’TS. If it’s a DON’T, maybe suggest some alternatives that aren’t bras but also aren’t turtlenecks. Offer to loan her something fabulous of your own or show her pictures of great bra-adjacent looks she can pull off. There are absolutely ways to incorporate lingerie into an outfit without looking like you ran out into the street because the fire alarm went off. I agree that you should try not to judge her style. Amanda and I lived through the ’90s together and we certainly are no one to judge.

Dear Ruthless,

What is the protocol for approaching a celebrity in public? I really love telling artists their work moves me, but I also don’t want to be rebuffed and feel like a jerk.

Signed,

Super Fan

Dear Super,

AMANDA: It’s important to read the vibe. Are they being hustled into a car, flanked by a security team? Best probably to leave it. Are they waiting in a doctor’s office for a breast exam? Admire from afar. Are they in the middle of a meal and conversation? Let them eat and maybe approach them when their meal is done or as they’re leaving. I’ve had wonderful interactions reaching out to celebrities I admire. Paul McCartney gave me a kiss on the cheek! Barabara Cook discussed her interpretation of a Sondheim song! Sara Bareilles is a walking angel on earth. And not so good: Dave Letterman reacted like I had assaulted him. Paul Simon rolled his eyes and looked at me like I had cooties. Sometimes it’s better not to meet your heroes?

CINDY: Most of my celebrity sightings have occurred without any input from me and involved minor violence. When I was 13, I was with my parents in Tiffany’s and Chevy Chase ran by and knocked me over. Why he was running in Tiffany’s, I cannot conjecture. Years later, I was auditioning for drama school, and John Malkovich ran into me on the stairs at Circle in the Square. Again, I fell over. Once, during a pick-up soccer game my husband coerced me to join, a celebrity I shall not name shot the ball right into my face, broke my glasses, and nearly knocked me out. So mostly I avoid these people.

Dear Ruthless,

Every year my building prepares for a doorman strike by making a sign up list and issuing various dire warnings. This year they are making us have ID cards. There hasn’t been a strike since 1991. Can we dispense with the charade?

Signed,

Charade Hater

Dear Charade,

AMANDA: Only at your peril. Just because it hasn’t happened in a long time, doesn’t it mean it can’t or won’t. Your apartment may not have been flooded (hopefully), but does that mean you stop paying homeowner’s insurance? Just because you haven’t been hit by a meteor, you should still always have on clean underwear when you’re out in public, just in case, *tuh tuh.*  My ancestors were always prepared for the Cossacks to come.  [And they usually did]. Better to be safe—and ready to have to pick up your Door Dash in the lobby.

CINDY: Most buildings have any number of social, chatty tenants who would enjoy a shift or two at the front door. If you are not one of them, get your ID picture taken and show gratitude to the signer-uppers. If you live in a small building where it might be all hands on deck, you may have to suck it up, join the effort to the extent you are able, and remember how lucky you are not to be on your feet for eight-hour shifts, sorting hundreds of pieces of mail, or lugging your and your neighbor’s garbage to the street.

Dear Ruthless,

I received a thank you email from an industry colleague after doing a fairly large favor for him—introducing him to the head of a big company, who, thanks to my intervention, has become his new, lucrative client. I’m very glad to have his gratitude but I’m pretty positive the email was written using AI, which seems to me to be the height of laziness. Do I speak to him about it?

AI No Thanks

Dear AI No,

CINDY: I find any use of AI other than asking it how to put together a vacation or to suggest a wine to pair with your chicken dish infuriating. Writing is a skill and often an art and once people stop being able to put their own thoughts onto paper or computer, we’re doomed as a civilization. That’s on top of climate change. Now, what to do about the colleague? If you care about the future well being of Lazybones, propose a coffee date under the pretext of asking how the new work is going. Then gently suggest that AI-written missives are often identifiable and the practice might warrant a rethink. On a personal note, I believe a nice bottle of Scotch, a case of oranges, or a donation to your favorite charity is an appropriate thank you for such a lucrative favor.

AMANDA: Great question! There are several possible answers for that—happy to take you through them. Would you like me to take a deeper dive? Is there anything else I can help you with today? Nice top! Yours Sincerely, Amanda.

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.