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

October 13, 2026 | 8:18 AM
in ABSURDITY, COLUMNS, NEWS
0

By Cynthia Kaplan and Otis, a Welsh terrier

According to the paper of record, the WSR, a family of barn owls have been sighted on the water tower atop a building on West 75th Street. Very exciting unless, like your Ruthless Advisors, you’ve seen The Staircase, a 2020 miniseries starring Colin Firth as crime novelist Michael Peterson, who is accused of murdering his wife, played by Toni Colette, after she is discovered dead at the bottom of their home’s staircase. The series employs an unusual device to keep the viewer guessing; it depicts the moment of death three times, with three different causes.

In one version of the killing, on an evening sometime around the Christmas holiday, Toni Colette walks out the front door of their North Carolina home to bring in (or out, who can remember) a couple of ornamental deer or somesuch. Out of nowhere, she is attacked on the head by an owl, whose talons draw blood. Terrified, she slaps it away, reels into the house, and staggers up the stairs to treat her wounds. On her way back down, towel to her head, she slips in her own blood, strikes her head on the wall, and dies. As we mentioned, it’s just one theory, and ultimately Colin Firth goes to prison for the murder. Nevertheless, your Ruthless advisors recommend that you do not walk along 75th Street without wearing a hat.

Dear Ruthless,

Every year at our kids’ birthdays, my mother comes to celebrate, presenting gifts for both the birthday boy and the non-birthday girl. Or vice versa. I’ve asked her not to because I’m trying to teach my kids that some days are for celebrating others. Some days they get gifts (or their way, or ice cream, or whatever) and some days they don’t. And that needs to be okay. I’ve tried to explain this, but she insists she is exempt from teaching them lessons. What???

Signed,

Annoyed

Dear Annoyed,

CINDY: Grandparents are an unruly, often free-wheeling lot. Part of the beauty of being a grandparent (or an aunt or uncle) is spending time with adorable children while not having to be enforcers. I understand your annoyance but I honestly don’t think this issue requires a beefy response. I’d save your ire for a real doozy, and believe me, there will be plenty of those. If it really bothers you, ask your mom to maybe hold the extra gift until after the celebration, to be given in private to the non-birthday child.

OTIS: Really, what’s your problem? It’s a joy to receive a gift you weren’t expecting on a day you weren’t expecting it. YOU teach your kids the important lesson about taking turns being the center of attention. Let your mom teach them about unbridled generosity. And as someone who doesn’t know how to expect gifts, I lose my mind when one shows up out of the blue. Especially if there is a squeaker.

Dear Ruthless,

I’ve noticed pleats are back. Why?

Signed,

Ugh, Pleats

Dear Ugh,

OTIS: I don’t know which is stupider, the pleats or the question. No comment.

CINDY: Retail companies want you to buy new pants and they’ve come up with the only thing we all definitely purged our closets of. Most of us always have some selection of straight pants, skinny pants, wide pants, boot cut pants, flappy pants, ankle length pants, even, dare I say, jeggings, knowing that every year or two, we have to pull out one shape or another to stay on trend. But the last thing we imagined would happen was a return to the almost never flattering pleats. Solidarity is the key here. We’ll march if we have to.

Dear Ruthless,

My girlfriend and I were at my good friend’s wedding last month. A group of us got together beforehand and wrote a short presentation. We were the last of the speeches, and at the end, I was really overcome with emotion. I took the mic, yelled, “And we’re next!” turned to my girlfriend, who was part of the group, got down on one knee, and proposed. She said yes and everyone cheered. Since then, the bride and groom are pissed at me and I’m not sure why they should be. It was a great night, and I just seized the moment, right?

Signed,

Engaged and in Trouble

Dear Engaged,

CINDY: You seized someone else’s moment. Other people’s weddings are not opportunities for you to make personal pronouncements. Years ago my now-brother-in-law wanted to announce his engagement at our wedding. He PLANNED to announce it at our wedding, after proposing on the plane there to his girlfriend. Our answer: a hard no. Honestly, people getting married do that infrequently enough, hopefully, that they shouldn’t have to share their thunder. You owe your friends a sincere apology, with no “I just…” No one cares what you just. Just some other time.

OTIS: You got the zoomies. There was a lot of noise and excitement and you lost your cool. This has happened to me and while I don’t apologize, per se, I have been sent off to another room to think/not think about what I’ve done. I agree with Cindy. You have a mouth on your face and you speak words. Your move.

Cynthia Kaplan is the co-creator, with Karen Bergreen, of this column and of The Ruthless Comedy Hour, a comedy variety show for grownups with brains. In its 12 years, the Comedy Hour featured top stand-up comedians musicians and celebrity interviews, and addressed 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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