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

October 28, 2025 | 8:44 AM - Updated on November 10, 2025 | 12:07 PM
in ABSURDITY, COLUMNS, NEWS
16

By Karen Bergreen and Cynthia Kaplan

Fall greetings from your Ruthless Advisors. Lot’s going on. Karen is in Spain doing research on what kind of advice Spanish people need, just in case we decide to emigrate, and Cindy is deeply engaged in a survey of candy in order to advise you on your best Halloween candy-giving options. Her choices are as follows: Milky Way, Twix, and for those who like a nut option, Snickers. Nothing with coconut unless you are only getting candy for Karen, who loves an Almond Joy.  And no boxes of raisins. That “nature’s candy” thing is a load of BS. But definitely do put candy corn out around the house in small decorative dishes.

Dear Ruthless,

I accidentally cut someone off with my cart at Trader Joe’s. I heard her mutter “Of course.” This happened two weeks ago and I can’t stop thinking about it.  How do I get my equilibrium back?

Signed,

Still Haunted in Aisle Three

Dear Haunted,

CINDY: I once was in the orthodontist’s waiting room with my kid. This was around the time that palate expanders were becoming a thing. I said out loud that they sounded like medieval torture devices. There was another mother there with her kid, who was about to get one, and she gave me a dirty look.  I felt horrible and wrote a note for the receptionist to give to her, apologizing for my big mouth. I got a nice note back. Apologies for our bad behavior are good for the soul of the person we harmed as well as our own.

KAREN: I’m with Cindy on this. I would hang out at Trader Joes until you see her again and then apologize.  If you don’t have time for that, perform an act of kindness for someone you don’t know.  Pay for their coffee, hold a door, let someone cut in line. You don’t owe it to that woman, but you do owe it to yourself to stop carrying her “of course” around like it was a final judgment.

Dear Ruthless,

When I’m on social media too much I hate myself, but when I cut down I feel disconnected. Is there a middle ground?

Signed,

Put the Phone Down?

Dear Put,

KAREN: Passive lurking is a recipe for disaster, but we have gotten accustomed to this digital fix. Perhaps you could post something when you go on.  It doesn’t have to be something deeply personal or controversial.  Maybe a pretty building or a delicious food.  Hopefully, you’ll get a few responses, feel connected and live your life with your real friends.  Call them or plan a visit.

CINDY: I hear you, Friendsis. It’s really hard to get out of the habit of checking up on what our friends are doing or seeing how many people liked the picture you posted of Otis. Consider getting a flip phone and going out into the world. Take a class, meet friends for coffee, or call them on the phone. I mean, what’s up with the new thinking is that calling is rude?

Dear Ruthless,

A woman in my friend group always finds a way to mention her apartment’s square footage, even when we’re talking about the weather.  I can’t bear it.  Do you have advice for me?

Signed,

Joan’s Two Bedroom

Dear Two Bedroom,

KAREN:  Respond with your apartment’s square footage and how much you paid.  Then add your height, your weight and your net worth.

CINDY: Karen is really good at this type of question. No notes.

Dear Ruthless,

I’m a divorcee in my mid-fifties and for the past month I’ve seen the same attractive gentleman in my subway car several times on the way to work. No wedding ring. I’m pretty sure he has noticed me, too. Is there some non-weird way to introduce myself or ask him for coffee?

Signed,

Subway Sweetie

Dear Sweetie,

CINDY: Life is short and full of surprises and opportunities if we would only get out of our way. I know two lovely people who met on the subway. You can go the direct route: get up, sit down next to him, and introduce yourself. Or you can go the indirect route: eat a pastry while standing above him and then apologize when bits float down to his lap.

KAREN: I’m already invested in this. You need to go for it. Smile nicely, make small talk about something going on in the moment, the crowd, an on-subway dance performance, the weather. If he  gives you any sort of positive feedback like a big smile or a cute answer then you could say something like: We keep running into each other, shall we make it official and go for coffee?  Even though I’m excited for you, I need to remind you that not all married men wear rings.

Dear Ruthless,

How does one not eat all the leftover Halloween candy?

Signed,

Sugar Coma

Dear Coma,

CINDY: I’m sorry, but totally I’m stumped.

KAREN:  The obvious answer is to douse it in Tom Ford’s Rose fragrance or gasoline, or you could give it away.

Read all Ruthless Advice columns here.

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West Side mom
West Side mom
20 days ago

Let the “Ruthless” columnists know that pediatric dentist Jerry Ashrafi (WEA & 69 st) receives Halloween candy back from his kid patients, paying the kinder $ for the sweets, and donates the candy to… who knows where?!

5
Reply
Edge of UWS
Edge of UWS
18 days ago
Reply to  West Side mom

Thanks for this. Was looking for a pediatric dentist in the area.

0
Reply
Ruthless’ Biggest Fan
Ruthless’ Biggest Fan
20 days ago

THanks for the daily dose of laughter Cindy and Karen! Can’t wait for your very special Ruthless comedy hour: NY Comedy festival edition on SUNDAY 11/9 at 6pm at NY comedy Club on W 78th st with very special guest CNN’s Michael Ian Black

6
Reply
Peter
Peter
20 days ago

Plot twist: the apartment is 243.7 sq. ft and is rent-controlled.

4
Reply
Joey
Joey
20 days ago

You are much too kind to Still Haunted in Aisle Three.
Still Haunted in Aisle Three Should put it in the rear view mirror and move on.

1
Reply
Westside rag reader
Westside rag reader
20 days ago

Haha to not all men wear rings, so true. I prefer the subtle advice idle chit chat to gage his interest, then pumpkin latte here I come!

4
Reply
Hannah Brown
Hannah Brown
20 days ago

Maybe the subway woman could ask a question or make a comment about subway service, like do you know if there are delays on the 2 and 3 today? Just a suggestion.

2
Reply
Susan
Susan
20 days ago

Always funny but yet underlying good advice.

2
Reply
UWS Prof
UWS Prof
20 days ago

To Subway Sweetie – You could use the old line. “Come here often?” Good for a chuckle and tests his sense of irony. Good luck!

4
Reply
OPOE
OPOE
20 days ago
Reply to  UWS Prof

Or just show some skin.

0
Reply
JoJo
JoJo
20 days ago

I’m not sure I can trust advice from someone whose Halloween candy doesn’t include Reese’s! #1, always. Preferably the miniatures.

1
Reply
Cindy
Cindy
20 days ago
Reply to  JoJo

Reese’s used to top my list, but I’ve been converted to the Trader Joe’s version, which don’t come individually wrapped. Glad you stood up for them!

2
Reply
Cindy
Cindy
19 days ago

I never leave comments on posts. But…. “you ladies never disappoint!”

2
Reply
Dino Vercotti
Dino Vercotti
18 days ago

Dear Sweetie, Are you at least as attractive as the man you’re eyeing? Something to consider.

0
Reply
Jayne Martin
Jayne Martin
14 days ago
Reply to  Dino Vercotti

Attraction can’t be measured in just exterior looks! I was introduced to a man who I thought was literally ugly. But when I got to know him he became the most handsome man alive!

1
Reply
Jayne Martin
Jayne Martin
14 days ago

I put the Halloween candy in a bag and stomp on it. And then thrown in the trash and pour disgusting garbage on it

1
Reply

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