West Side Rag
  • TOP NEWS
  • OPEN/CLOSED
  • FOOD
  • SCHOOLS
  • OUTDOORS
  • REAL ESTATE
  • ART & CULTURE
  • POLITICS
  • COLUMNS
  • CRIME
  • HISTORY
  • ABSURDITY
  • ABOUT US
    • OUR STORY
    • CONTRIBUTORS
    • CONTACT
    • ADVERTISE
    • GET WSR FREE IN YOUR INBOX
    • SEND US TIPS AND IDEAS
West Side Rag
No Result
View All Result
No Result
View All Result

Favorite WSR Stories

    SUPPORT THE RAG
    Get the neighborhood news that matters.
    Sign up for our free newsletter

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

    October 1, 2024 | 9:45 AM - Updated on November 10, 2025 | 12:12 PM
    in COLUMNS
    20

    By Karen Bergreen and Cynthia Kaplan

    Hello again from your hyper-local Ruthless Advice columnists Karen and Cindy! We realize some of you are deeply concerned with the future of democracy and may not think to seek advice on more mundane matters, while others need advice no matter the travails of the wider world. We are here for all of you and will continue to be so, even if we have emigrated to Mustique by mid-November.

    Kindly send your dilemmas to Info@westsiderag.com, subject line, Ruthless, and we will employ our universal lack of expertise to solve them.

    Dear Ruthless,

    I’d love to hear you guys address whether parents should insist on using Life360 [a location tracking app] for college students over 18, not with their consent necessarily, but under duress?

    Signed,

    JY

    Dear JY,

    KAREN: If it were up to me, my college-aged kids would be microchipped and equipped with a security detail, but alas that’s not what is done. I’ve noticed that many parents choose to spy on their kids without their consent but it’s not fully reliable. I got my kids to agree to share their locations with me as long as I share mine with them. Be aware, however, that crafty teens can easily circumvent tracking apps by separating themselves from their devices.

    CINDY: I feel much better when I don’t know where they are and what they are doing all the time. I’m already on Facebook and X and that’s enough people to keep track of.

    Dear Ruthless,

    I have a house guest who won’t leave. She came for what she said was a weekend to catch up and see shows, but it’s Monday afternoon and as far as I’m concerned, the weekend is over.

    Signed,

    Annoyed

    Dear Annoyed,

    KAREN: I suggest you needlepoint a pillow with one of my favorite Ben Franklin sayings: Guests, like fish, begin to smell after three days.

    CINDY: Strip the bed and eighty-six the towels.

    Dear Ruthless,

    My mother-in-law bought me a sweater I will never wear and can’t return. Do I need to wear it in front of her? I hate how I look in it.

    Signed,

    Amanda

    Dear Amanda,

    CINDY: Over the years, my mother-in-law, a thoughtful and generous person, has bought me all manner of gifts, the pinnacle (or nadir) being a white, pearl covered beret that I believe she may have bought for herself (she loves sparkle; I do not) and given to me when she found herself short a Hanukkah gift. I shall not wear this publicly. However, I recommend wearing all gifts, especially a pearl encrusted beret, at least once to please your MIL with the added benefit of her seeing how terrible it looks on you.

    KAREN: You need to wear the sweater. And often. Unless you loathe your spouse, in which case, you can re-gift it back to your mother-in-law for the next family celebration.

    Dear Ruthless,

    I go out to walk my dog in Central Park every morning and socialize with lots of people. There’s one very sweet woman who always approaches me with her big, shaggy Sheepdog. The problem is, the dog drools…I mean really drools…and I can’t bring myself to stay and talk to her. I’m afraid she feels rejected. I’ve thought of telling her my problem. Should I?

    Signed,

    Squeamish

    Dear Squeamish,

    KAREN: First of all, I love a sheepdog, but that doesn’t necessarily influence my answer. Second, and more importantly, you should spend as much time with that dog as possible. There will be a time when your human loved ones drool…I mean really drool…and you need to prepare yourself.

    CINDY: If the dog drools all over you, he/she/they drool all over everyone else, including the owners. It will not be a news flash to let them know that you are trying to preserve your outfit for the day. Or wear coveralls and delight in the sheepdog and a new friendship.

    Dear Ruthless,

    Is it evil to feel a sense of schadenfreude over the indictment of Mayor Adams?

    Signed,

    Possibly Evil Person

    Dear Possibly Evil Person,

    CINDY: No.

    KAREN: I’m guessing your real name is Bill de Blasio.

    See previous Ruthless Advice HERE.

    Subscribe to West Side Rag’s FREE email newsletter here.

    Share this article:
    SUPPORT THE RAG
    Leave a comment

    Please limit comments to 150 words and keep them civil and relevant to the article at hand. Comments are closed after six days. Our primary goal is to create a safe and respectful space where a broad spectrum of voices can be heard. We welcome diverse viewpoints and encourage readers to engage critically with one another’s ideas, but never at the expense of civility. Disagreement is expected—even encouraged—but it must be expressed with care and consideration. Comments that take cheap shots, escalate conflict, or veer into ideological warfare detract from the constructive spirit we aim to cultivate. A detailed statement on comments and WSR policy can be read here.

    guest

    guest

    This site uses Akismet to reduce spam. Learn how your comment data is processed.

    20 Comments
    RCP
    RCP
    2 years ago

    This is great. Wish I had the courage to ask them a question, but I’m afraid the brutal honesty would break me.

    7
    Reply
    Purgatory
    Purgatory
    2 years ago

    The responses to Possibly Evil Person are comedy gold. One of my coping mechanisms to what’s going on with democracy is to remember to laugh once in a while, and this column is just the medicine I need.

    Last edited 2 years ago by Purgatory
    6
    Reply
    Tom
    Tom
    2 years ago

    I visited Mustique years ago, so beautiful! I’m jealous of anyone who can go there during the colder months here!

    1
    Reply
    Cindy
    Cindy
    2 years ago
    Reply to  Tom

    Omg, we don’t know anyone whose been to Mustique. Are you a rock star?

    1
    Reply
    Westside reader
    Westside reader
    2 years ago

    Love this new column I laughed out loud at some answers, would be nice to have pictures accompany some questions ie pearl beret, or yucky sweater to give it an extra lol. I’m hooked!
    Will look forward to your next addition weekly? Monthly?

    3
    Reply
    Cindy
    Cindy
    2 years ago
    Reply to  Westside reader

    Every two weeks. Send us a question!

    3
    Reply
    Susan Perry
    Susan Perry
    2 years ago

    Love this column! More please!!!!

    8
    Reply
    fran
    fran
    2 years ago
    Reply to  Susan Perry

    Agree!!

    2
    Reply
    Big fan💕
    Big fan💕
    2 years ago

    Sage wisdom from these ladies ! Anyone interested in seeing more of them, you can check out their next live performance Tuesday, October 29th at 7:30pm at New York Comedy Club 236 W 78th St. Special guest is the Daily Show co-creator Lizz Winstead!

    5
    Reply
    Lori
    Lori
    2 years ago

    Dear CIndy, that fish thing was Oscar Wilde 🙂

    1
    Reply
    Cindy
    Cindy
    2 years ago
    Reply to  Lori

    We Googled. It was definitely Benjamin Franklin. Best leave it to the non-experts, Lori, but we love your enthusiasm!

    3
    Reply
    Cindy
    Cindy
    2 years ago
    Reply to  Lori

    Hahahaha Karen wrote that response.

    1
    Reply
    Cindy
    Cindy
    2 years ago
    Reply to  Cindy

    Lori, ask us a question so we can give you more smug advice!

    0
    Reply
    Katherine
    Katherine
    2 years ago

    This was delightful.

    4
    Reply
    Bounder
    Bounder
    2 years ago

    For the dog drool phobe;

    Two words, “dog clothes“. You have a dog. You are in the park daily for pre 9 off leash romps and you don’t have a “dog clothes” uni?…

    3
    Reply
    Squeamish
    Admin
    Squeamish
    2 years ago
    Reply to  Bounder

    It is not about clothes, but a weak stomach.

    1
    Reply
    Father Hennepin
    Father Hennepin
    2 years ago

    I sent a question, but they clearly couldn’t or wouldn’t answer it. That’s ruthless.

    0
    Reply
    Steve M
    Steve M
    2 years ago

    If this WASN’T the UWS, I would say all these questions sound made up.

    1
    Reply
    Life-long Upper West Sider
    Life-long Upper West Sider
    2 years ago
    Reply to  Steve M

    But it is!!!

    1
    Reply
    Cindy
    Cindy
    2 years ago

    Cindy here. I received this message and have been asked to quote the writer in the comments, as she sometimes has trouble with computers. “I think Cindy should take that lovely-sounding sparkly white beret, wrap it up nicely, and give it back to her mother-in law for Hanukkah this year. I’m guessing since she is old, she may not even remember having given it. Signed, Cindy’s mother-in-law”

    1
    Reply

    YOU MIGHT LIKE...

    COLUMNS

    Upper West Side Historical Photo Challenge No. 37

    October 6, 2026 | 8:00 AM
    Upper West Side Street Life as It’s Seen Today: Photo Collection
    ART

    Upper West Side Street Life as It’s Seen Today: Photo Collection

    October 5, 2026 | 3:11 PM
    Previous Post

    Man Indicted For 2 Antisemitic Attacks on the UWS: Manhattan DA

    Next Post

    Construction Begins on Redesign of New 96th Street Bus Lanes

    this week's events image
    Next Post
    Construction Begins on Redesign of New 96th Street Bus Lanes

    Construction Begins on Redesign of New 96th Street Bus Lanes

    Tim Walz Spotted Running in Central Park Hours Before Vice Presidential Debate

    Tim Walz Spotted Running in Central Park Hours Before Vice Presidential Debate

    Meet the Founder of Living-Wage Cleaning Company Well-Paid Maids

    Meet the Founder of Living-Wage Cleaning Company Well-Paid Maids

    • ABOUT US
    • CONTACT US
    • NEWSLETTER
    • WSR MERCH!
    • ADVERTISE
    • EVENTS
    • PRIVACY POLICY
    • TERMS OF USE
    • SITE MAP
    Site design by RLDGROUP

    © 2026 West Side Rag | All rights reserved.

    No Result
    View All Result
    • TOP NEWS
    • THIS WEEK’S EVENTS
    • OPEN/CLOSED
    • FOOD
    • SCHOOLS
    • OUTDOORS
    • REAL ESTATE
    • ART & CULTURE
    • POLITICS
    • COLUMNS
    • CRIME
    • HISTORY
    • ABSURDITY
    • ABOUT
      • OUR STORY
      • CONTRIBUTORS
      • CONTACT US
      • GET WSR FREE IN YOUR INBOX
      • SEND US TIPS AND IDEAS
    • WSR SHOP

    © 2026 West Side Rag | All rights reserved.