When Is It O.K. to Date a Friend’s Ex?

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Social Q’s

An old friend dated a really nice guy for a few months, but it fizzled. I definitely felt a spark when we met, but kept it to myself. Months later, I bumped into him at a yarn shop. He invited me out. I told him I would like to go but wanted to ask my friend for her blessing first. When I did, she said, “Absolutely not” — without further explanation. How bad would it be for me to disregard her answer? (Note: I am pushing 40 and don’t feel sparks every day.)


Save your breath, Ami. You had me at yarn shop. A mate who knits has long been my fantasy — or a nurturing doctor in certain subspecialties. Sadly, I failed on both counts. So, let’s see if we can grab this brass ring for you.

You characterize McCrafty’s ex as “an old friend.” But this raises questions: Is she a close friend? In the Venn diagram of your social circles, is there considerable overlap? And could you live with her rejecting you for overruling her preference (and badmouthing you to your pals in common)? This is a lot to stake on a mere “spark,” no?

Still, your friend’s knee-jerk refusal to bless the date, after having seen this fellow for just a few months, seems selfish. You can always approach her again, if her adamant reply strikes you as out-of-keeping with her better nature. But I might skip this step and simply weigh your desire to go to dinner with the knitter against your friend’s opprobrium. We can’t have it all. So, which means more to you?

If you decide to see him, let your old friend know as soon as you have an inkling things may work out. It will be better for her to hear it from you. And if you decide to move forward — on which I pass no judgment — a note for next time: Don’t ask permission if you don’t care about receiving it. (Also, email me the second you get to quiet nights knitting cashmere socks and listening to Joni Mitchell, understood?)

Be a Child Tamer

I am the grandmother of a 2½-year-old. I take her to a park in Chicago where she loves to play. Lately, a 4-year-old boy charges at her every time we arrive, throwing his hands in the air and roaring. It frightens her, and she asks to go home. His nanny, who is not a native English speaker, seems indifferent; she just keeps chatting with the other nannies. How should I handle this?


Score one for the playground at Washington Square Park. That boy (and his minder) would be in shackles in 15 minutes. I’m not sure why you have written off the nanny simply because she is speaking another language with her associates. This is her job. Say: “Excuse me. Your boy is scaring my granddaughter. Please have him stop screaming and running at her. She’s just a toddler.”

The nanny may surprise you and handle this brilliantly. If she doesn’t, speak to the boy yourself. While remaining mindful that you are speaking with a child, say: “Stop it! You’re frightening her. And that’s mean.” Or escort the boy to his nanny and work out an agreement. What may seem like blowing off steam to them is playground bullying to you (and me). You’re an adult; shut it down.

It Pays to Talk

My husband and I are in our early 30s. We work hard, in tech and finance, and we’re saving to expand our family someday. Recently, we declined an event invitation from his relative because of its cost. Shortly after, we accepted another invitation from him, assuming it was for drinks, which turned out to be a restaurant dinner for 15. When the bill came, this relative asked my husband to pay one-third. He did! I was annoyed at my husband for not pushing back, and at the relative who probably asked my husband to pay more because he’s “in finance.” How to proceed?


Funny thing about your question: When I read it, the Beatles song “Two of Us” popped into my head — about the pleasure of aimless and (relatively inexpensive) drives in the country. (It was probably the lyric, “Two of us riding nowhere, spending someone’s hard-earned pay.”)

For starters, get on the same page with your husband about your budget. Maybe he’s looser with the reins and you’re a little tighter? But if you’re pooling money, agreement is required. He may want to include some spending that seems crazy to you, like paying more at family events. But I bet you can work out a compromise.

Once you have, it will be simple to deal with invitations. If they fit into your agreed budget and you want to go, accept. If not, decline. (Again, more compromising may be required.) With folks whose parties tend to be pay-to-play, don’t be shy about asking what their soirees will set you back. How else will you decide? (And if you have three spare minutes, listen to Aimee Mann and Michael Penn’s cover of “Two of Us.” It’s lovely.)