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

By Karen Bergreen and Cynthia Kaplan

It’s finally sweater weather in New York. Did you notice that big sweaters are back, not those wide ones that still show your bellybutton, but boxy sweaters that hang past your wrists and to your hips? Sure, your waist disappears, but this can be a bonus. Also, flappy pants are back. I guess it’s going to be one of those seasons where you can eat anything you want and no one will know. In today’s worrisome world, any reason not to worry is a win.

Also, some Ruthless advice for the financially comfortable: Consider a donation to your local food pantry.

Dear Ruthless,

My 24-year-old daughter only calls when she needs something. I don’t like it but don’t know how to fix this.

Signed,

Mother of Convenience

Dear Mother,

CINDY: Your 24 year-old daughter is living her life. When she needs something, who else is she going to call? I consider it a high compliment to you that you are her go-to person. When I was 24, I didn’t want to chat that much with my mom, and she was great. Unless your daughter is asking for inappropriate things, like a new Rolex, give her space and be there for her.

KAREN: Maybe you could drop breadcrumbs at the end of each phone call.  Like “Oh Darlene, I’m rushing off but I wanted to tell you about the $10,000.”  Or “Oh Serena, I have company but I heard the craziest thing about you today.”

Dear Ruthless,

I’m considering quitting my job because I’ve grown to hate it. I can’t tell if I’m just burned out, unmotivated, or in the wrong profession entirely.  How do you know when it’s really time to leave?

Signed,

Weary Worker

Dear Weary.

CINDY: How do you feel when you think about leaving? Anxious? Relieved? Is there some other company or job you’ve thought about but haven’t had the nerve to make the move? If you can afford to take a risk, look for something or somewhere new. I’m a big believer in reinvention at any age. Look at us, we’re advice columnists!

KAREN: At the very least, see what’s out there.  Also, consider taking on a fun hobby. Sometimes a creative activity can breathe new life into other aspects of your day-to-day.  And, if you can treat yourself to a vacation, do so.

Dear Ruthless,

We loaned our jogging stroller to a family in the building. Theirs had lost a wheel, it was a beautiful weekend, and we were happy to do it. They are very nice, our kids are the same age, and I see us being friends. But they haven’t fixed their stroller or bought a new one. They keep borrowing ours–we keep it in a shared basement. Yesterday it was gone when I went to take my son for a run. How do we ask them to stop?

Signed,

Neither a Borrower, Etc.

Dear Etc.,

KAREN: Time to keep the stroller in the apartment.  If you don’t have space, put the baby in the basement.

CINDY: Good neighbors need good boundaries. Let your new neighbors know that you are ready to have your stroller back full time or that your schedule has changed and you will not be able to plan ahead, so you want your options open. Otherwise, consider the story about the skaters Tonya Harding and Nancy Kerrigan and act as your conscience permits.

Dear Ruthless,

I accidentally liked my crush’s Instagram post from 2018. Do I fake my own death or pretend it was intentional?

Signed,

Mortified

Dear Mortified,

KAREN: The key is composure. Don’t even try to explain it. I’m not against a fib under the right circumstances, but those don’t exist here. You liked an old post because you were digging—we all do it. Sometimes I’ll get obsessed with someone’s feed for no reason and suddenly I’m scrolling through their 2016 vacation. Maybe just message him about the post so it’s out in the open. At least then the weirdness becomes conversation instead of evidence.

CINDY: You are not the only one who ever responded to a post without checking the date. They seem to show up of their own accord. Sending condolences for a cat who died in early 2005 is not unheard of. There’s a remedy I’ve been hearing about for social media agony that I think is really smart: Go outside and touch grass.

Read all Ruthless Advice columns here.

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