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

April 28, 2026 | 8:34 AM
in ABSURDITY, COLUMNS, NEWS
0

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.

April is not the cruelest month. February is. Seriously, one poem and April gets a bad rap? We here at Ruthless think April is pretty great. We’ve stopped dressing in head to toe wool and performance fabrics and we’re leaving the apartment for more than just the necessities. Most of all, we’re seeing our friends again! We’re meeting them on street corners, strolling the avenues together, and snacking at outdoor cafes. Friends are so important! Take time this spring to reach out to the ones you’ve been missing, check in on the ones you’ve been worried about, get yourselves outside for meet ups, park walks, and bike rides in your bike helmets. Also, Your Ruthless Advisors would like to take this opportunity to welcome the West Side Rag’s newest columnist: Scott Etkin of UWS Shed Watch. Your shed queries can now be sent directly to the expert!

Dear Ruthless,

I’ve been asked to be best man by a friend I’m just not that close to. I don’t know if I’m the default person, or he just likes me, or thinks I’d pull some good best man weight, but I’d like to say thank you but no thank you. I have no idea how to do it.

Signed,

Okay Man

Dear Okay Man,

CINDY: This is a hard one. Being a best man or best woman (the whole maid thing is like, yuck) is an honor but can also be a burden, both time-wise and financially. If you really want out, I see two options. One, tell him you have another obligation on that date. This is if you are okay skipping the wedding entirely. Two, try honesty. Tell him you are deeply honored but feel you are just not the right man for the job. Perhaps you can offer to talk him through his options and help him come up with a friend better suited.

AMANDA: I don’t know. I think you have to go through with it. He reached out to you for whatever reason to support him. And it’s an honor. Maybe you’ll grow close over the process. So start planning the Bachelor Party (no strippers please! Keep it classy!) and Best Man up bruh!

Dear Ruthless,

My neighbors and I share access to our small building garden. It is kept neatly,  with some mismatched furniture and a patch of grass my husband mows with an old rotating mower. Now that spring is here, I’d like to do some planting, maybe get some nicer furniture, and use the garden more often. I’ve polled the building to gauge interest and whether people are willing to chip in. They aren’t. Should I just go ahead at my own expense? I worry I’ll be mad when everyone enjoys the free fruits of my labor.

Signed,

Gardening for Group

Dear Gardening,

AMANDA: Ah, do it! Get the nice stuff you enjoy and enjoy it. And if others do too–good on them and you. Life and summer are too short. You can also feel free to borrow their nice gardening tools and partake of their chips and guac with impunity if they’re hosting a party.

CINDY: I agree. If you can afford to, and no one objects to having nicer stuff (I had a boyfriend once who got mad at me because I cleaned his bathroom. He felt judged. He was.) then garden away. There is a good chance people will thank you and may even ask to chip in after the fact or make a communal offering in return.

Dear Ruthless,

My new neighbor rides his bike everywhere, which is great, but I’ve seen him in the hood and it turns out he is one of those people who rides in the wrong direction and doesn’t pay attention to traffic lights. I think these people are thoughtless and a danger. Can I say anything to him without sounding like a scold or a buttinsky?

Signed,

Wary Walker

Dear Wary,

CINDY: Why can’t we bike like they do in Scandinavian countries? We’ve all seen the pictures. Riders stop at the light, and no one is in head-to-toe Lycra pretending they’re competing in the Tour de France. I would suggest you compliment your new neighbor’s climate-positive choice and tell him you’ve seen a lot of bikers riding against traffic and ignoring street lights and signs, and you certainly wouldn’t want to see him get hurt.

AMANDA: Buttoutsky, unless you find yourself in the elevator and can say with good will, “I see you riding against the traffic sometimes. That can be dangerous. Be careful.” Of course if you come into direct contact with him in that kind of situation, feel free to let fly with your New York best.

Dear Ruthless,

A very dear friend gives me beautiful birthday gifts. We have totally different tastes but she buys based on her own. I love her and don’t want to insult her but, oh, how I’d love to return some of these things and buy something I’d love. Should I tell her?

Signed,

Grateful, But

Dear But,

AMANDA: Depends. If they give you a gift and say something like “this is just so… you!” I think you have to keep it. Even if you secretly wonder if they really know you at all. Likewise, if it’s personal, precious to them, sentimental. If they get you a puce sweater, but you prefer blue (and really, why wouldn’t you?) I think it’s absolutely fine to exchange for something you’ll love and wear. Do you need to tell them you did so? Not unless they ask.

CINDY: Nope. Dear friends are hard to come by and you want to keep them. In a similar vein, my kind and generous mother-in-law often buys me clothes I would never choose for myself. I thank her profusely and wear the thing when I visit. Except for the white, pearl-encrusted beret, which some of you may remember from Chanukah, 2024. Sure, kind and generous mothers-in-law can be hard to come by, too, but that was a bridge too far.

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.

Amanda Green is a two-time Tony Award, Grammy-nominated lyricist/composer and award-winning performer. She currently serves as the first woman president of The Dramatists Guild of America. She is also a proud, life-long denizen of the Upper West Side. 

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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