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

By Karen Bergreen and Cynthia Kaplan

August is the Sunday night of summer. While August should be a delightful time to rest, vacation, and enjoy the waning of July’s heat, it is really just one long, stressful countdown to the start of school. Even if you don’t go to school anymore, the awful feeling that you might have to does not go away as you age.

Your Ruthless Advice columnists have some thoughts about how you might handle the impending sense of loss and doom. First, hydrate. Second, spend time with friends. Third, read for pleasure. No non-fiction, unless it is the paperback copy of “Empire of Pain,” about the Sacklers, which is both enraging and juicy. Fourth, spend time in nature, even if it is just near a tree in an island between Columbus Avenue and the bike lane. Fifth, eat al fresco whenever possible. All the fancy people are in the Hamptons and outdoor tables are yours for the asking. Finally, unload all your concerns here, and we will endeavor, as always, to relieve you of them.

Dear Ruthless

I’m part of a pretty intense tennis game at the Central Park courts at 93rd Street. We’ve been playing together for 10 years and are now in our mid 60s. One of the members had a health issue and has returned to the game a shadow of her formerly robust self. It’s killing the level of tennis. She’s a nice person, but what should we do?

Signed,

Sporty Friend

Dear Sporty, 

KAREN: This may be the most difficult question we have had since we began our column. There is something so heartless about kicking her out and yet you want to have a satisfying game in a city where tennis time is hard to find.  If the friend is only temporarily disabled, you should suck it up.  If this is a long-term proposition, you may want to hunt around on her behalf for better partners.  If she is a dear friend, I would suggest adding another game to your schedule. We all get old.

CINDY: I’m the worst skier among our friends. No matter how good I get, everyone else is better. So I occasionally take different runs and meet the others at the bottom. They cheer me on condescendingly when they see me coming and, oh wait, sorry, what was the question again? Right, tennis. You might want to hang in while your friend recovers both physically and psychologically from her health issue. You might also consider that she is trying to keep up for the sake of the group and would appreciate that you’ve noticed it is tough for her. Ask her what she would like, a gentler game with you or others, or to stick it out while she gets her strength back.

Dear Ruthless,

We’re about to become empty nesters. Any suggestions for how to weather this big life change?

Signed,

Nervous in the Nest

Dear Nervous,

CINDY: Don’t be nervous. Move your husband/partner into one of the kid’s rooms.

KAREN: Chilled Veuve Cliquot

Dear Ruthless

How do I know my contractor isn’t ripping me off?

Signed,

Joan C.

Dear Joan,

KAREN: This is NYC. Your contractor is ripping you off.  That said, you should compare pricing and scheduling with everyone you know.  I’m not good at this, but if something seems high to you or the group, shake your head and say, “Can you come down? This seems arbitrary. “

CINDY: How do you know if anyone is ripping you off? Do your homework, read reviews, get recommendations, check work and receipts. Hire someone who listens and is pleasant when you ask them to be accountable. Also, trust your gut. I don’t hire anyone I wouldn’t leave Otis with.

Dear Ruthless,

Are nanny cams still a thing? I kind of want to put one to use but I’m worried it’s unethical?

Signed,

Concerned Parent

Dear Concerned,

CINDY: See responses to the contractor question. Also, if you think you have cause to use a nanny cam, you have the wrong nanny and should move on immediately.

KAREN: I think they are really good when they video who did the murder in a police procedural.  And that’s about it.

Dear Ruthless,

How many free food  samples is too many?

CINDY: One million. Anything less is fine. Although since Covid, good luck finding even one.

KAREN: It depends on the size of your handbag.

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