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

September 30, 2025 | 8:20 AM - Updated on November 10, 2025 | 12:08 PM
in ABSURDITY, COLUMNS, NEWS
13

By Karen Bergreen and Cynthia Kaplan

It’s the High Holidays for Jews around the world, and that includes those on the Upper West Side. Huzzah!  It has always confused us that Yom Kippur, the Day of Atonement, is a week after Rosh Hashanah, the turn of the Jewish New Year. Meaning, we’ve only had one week to misbehave. Anyhoo, we’ve always found Yom Kippur, whether marked in a synagogue, at home, not celebrated, or ignored if you believe something else entirely, to be worthy of consideration. The task on Yom Kippur is not to just acknowledge our wrongdoings, but to apologize to anyone we may have harmed over the past year. Face to face. Personal accountability can only be a good thing in today’s rough world. And so, if we have in any way harmed you with our non-expert advice, we do sincerely apologize.

Dear Ruthless,

Every time I go out with a friend she insists on splitting the Venmo to the nickel, meaning not in half, but exactly who ate or drank what. It seems inelegant. Do I say something?

Signed,

Nickel and Dimed

Dear Nickel, 

KAREN: You’re right. Splitting the bill to the nickel is inelegant, but nothing about Venmo screams style. People are weird about money. They want to feel like they’re being fair and that they’re being treated fairly in return.  If you want it to feel less icky, you can lightly reframe it. Suggest alternating who picks up the check. Or just say, “I’ll get this one, you get the next.” It spares you the accounting, and it reassures her she isn’t being taken advantage of.

CINDY: Your friend may be on a budget you know nothing about and is making food and drink choices based on that. I would split the bill as she requests with a smile and give her some grace. And as someone who doesn’t drink much with meals, splitting a check evenly when your pal regularly has a bottle of wine to themselves doesn’t feel that elegant to me.

Dear Ruthless, 

My work wife is starting to expect more than my actual wife. She insists we eat lunch together everyday and makes me feel guilty if I’m not available for team drinks. I don’t think she has designs on me but I feel suffocated.

Signed,

Henpecked at the Office

Dear Henpecked,

KAREN: Boundaries are your friend. Set them. The sentence “I can’t do lunch every day” comes to mind. If she’s truly a friend, she’ll get it. And if she doesn’t,  you may  consider a work divorce.

CINDY: What is a work wife, anyway? Is it a colleague that does the work you don’t want to do? Like your real wife probably does? I mean, oh, forget it. As a writer who often works at home, I consider my lunch time sacrosanct. I like to eat and read my non-work book, which is more often than not a Scandinavian crime novel. If my real husband happens to be working from home, I make it very clear that not only do I not want to make his lunch, I don’t want to eat with him. I don’t even want him to make eye contact. Put on your big boy pants and let your colleague know that lunch is not only your work break but hers, as well.

Dear Ruthless, 

I just joined the PTA at my kids school and it feels like Mean Girls. I’m having horrible flashbacks to my own high school experience. My husband told me to drop it but I want to be involved. Advice?

Panicked Mom

Dear Panicked,

CINDY: There are PTA people and non-PTA people. It is okay to be either. If you, like me, found these meetings intolerable but still want to contribute, be a worker bee and sign up for the occasional class trip or bake some brownies. Let someone else argue about whether they have to be put in individually sealed wrappers.

KAREN: Joining the PTA is a great way to meet people. It’s irrelevant to the actual success of your kid’s experience. If the moms are horrific, run. This is a great opportunity to model for your children that they don’t need to put up with bullies just for the sake of fitting in. Take yourself to the movies.

Dear  Ruthless, 

Our building has a basement library full of books relinquished by tenants, most of whom have too many to begin with. It’s such a nice way to share resources. I always return books I’ve borrowed, especially anything recent. I’ve noticed lately that all the newest hardcovers and best sellers are disappearing and not coming back. I was recently invited to a gathering at a new neighbor’s apartment and you’ll never guess. They are all on her bookshelf!  Held together by bookends, like they now live there permanently! Do I say something to her? To the others? It really bugs me.

Signed,

Outraged on Riverside

Dear Outraged,

CINDY: A note posted in the library can possibly do the trick while keeping you anonymous: PLEASE RETURN RECENT RELEASES SO ALL CAN ENJOY.  Or, over the next few weeks, ask to borrow one book at a time and return it to the library.

KAREN: Don’t ever invite that neighbor into your home.  She’ll steal your silver.

Read all Ruthless Advice columns here.

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13 Comments
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Angela
Angela
3 months ago

Thank you for bringing us this column, it will make for some interesting conversations among my friends and I. HAHAHAHA… better than Dear Abby

6
Reply
Ruthless’ Biggest Fan
Ruthless’ Biggest Fan
3 months ago

Thanks for another day brightener Karen and Cindy! Can’t wait to see your live show as part of this years NY Comedy Festival on November 9th at 6pm at the New York Comedy Club on W 78th St!

4
Reply
Wijmlet
Wijmlet
3 months ago

From what I hear, including in my building, books left in a public place in the building are meant to be taken and not necesssarily returned.

I often leave books to be taken permanently.

11
Reply
Sarah
Sarah
3 months ago
Reply to  Wijmlet

I always thought that was the case for everything left in that kind of spot in the building, whether it be a book, a cardigan, or an old tchotchke…

6
Reply
Foodie
Foodie
3 months ago
Reply to  Wijmlet

Yeah. I don’t get the complaint or the resolution. Unless you are running it as a library and personally enforcing the rules for everyone (not just regarding your own books), give it a rest or just don’t donate.

1
Reply
Carmella Ombrella
Carmella Ombrella
3 months ago
Reply to  Foodie

Adding to the pile: in our building, books are left in the laundry room. Tenants and staff are free to take them, read them, sell them, donate them, return them (seldom happens) or make origami with them.

2
Reply
Elizabeth I
Elizabeth I
3 months ago

Why are these people doing math? Just tell the wait staff that the table needs separate checks from the start? In the rare event they won’t do it, you get out the calculator, but that should be a rare event.

11
Reply
Davids
Davids
3 months ago
Reply to  Elizabeth I

It depends how many diners there are. A number of restaurants I’ve been to recently will not provide more than two or three checks for a single table.

4
Reply
Peter
Peter
3 months ago

Work wife?! What grown man even utters that without “designs” of his own? Dude, you’re far away from home here…

1
Reply
Sarah
Sarah
3 months ago

I don’t mind people splitting the bill dish by dish, but then YOU HAVE TO BE ABLE TO DO THE MATH QUICKLY AND CORRECTLY. There is nothing worse than sitting there for fifteen minutes after dinner while someone flails around with the check, spattering their anxiety and incompetence on everyone. I was that broke once, too, but because I was broke I was well aware of what I was spending!

0
Reply
Splitskies
Splitskies
3 months ago

Check splinters:
Another suggestion that works well is to ask for separate checks !

2
Reply
Aida
Aida
3 months ago

Don’t forget your laundry in the laundry room, you’ll never find them you will find them, in her closet.

1
Reply
Kathy Hartzell
Kathy Hartzell
3 months ago

I’m going to make a pitch for the PTA, or PTSA. These groups usually have a rep attend school board meetings, they help get the word out to parents about changes in after school programs or matters pertaining to the school day. I was president, treasurer and chief bottle washer in PTA’s for a long time, and yeah, sometimes there was a mean girls aspect, but I found that more often in the room parents role! I do think there’s something to be had for being part of PTA and maybe doing something to get back to the mission for the group, goals for the year and cleaning up the vibe.

I left PTA, after attending two years of School Boards to have members ask me to run, and then served on the board for several years. Another very worthwhile role to play.

Give it a chance and stick to the basics, the work the PTA is meant to do on behalf of the kids.

3
Reply

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