What I Remember About the Moms Who Paid Me to Babysit

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Photo: Klaus Vedfelt/Getty Images

When I was living in New York City after college, babysitting meant going to an apartment nicer than mine and getting paid to sit on someone else’s couch. Each babysitting job was a glimpse into a possible future: The prewar apartment on the Upper West Side, framed New York Post covers hanging in the bathroom; the fully renovated Park Slope townhouse and the stunningly attractive husband who lived there; the Tribeca two-bedroom with a side-by-side washer and dryer and a Stokke high chair, suggestions that retaining pre-kid style and order was possible, for a price.

The kids were usually asleep when I arrived to babysit, the parents still getting ready to go out. The mom — always the mom — would let me in, often holding a glass of wine acknowledged by neither of us. She’d ask if she could get me a glass, and I’d decline, imagining what might happen if I didn’t. Then she’d disappear into the bedroom for the final touches while I took off my shoes, settled into the couch, and flipped through coffee-table magazines while trying to seem as natural as possible.

“You look so nice,” I’d say when she came back out, the husband hovering in the doorway. She might say something as illuminating as “Oh …,” both of us more than ready for them to leave. She needed to make her dinner reservation; I needed to judge her books and read the notes on the fridge, thinking forward to a time when a life like this might be mine.

My babysitting jobs were usually parents’ date nights, always for families who didn’t know me beyond an ad I posted on Sittercity. I love reading books, doing art projects, going to playgrounds, playing pretend games, and cooking. In 2014, four years after I stopped babysitting, a woman messaged and asked me to babysit her 2-year-old, noting we lived within a mile of each other. I marveled at being on the other side: By then, I had a 3-month-old. She’s 3 now, and my tolerance for “pretend games” lasts about two minutes.

One night, a 15-month-old charge woke up, and in the dark of the nursery — a tiny room off the kitchen of an Upper West Side prewar — I picked him up and rocked him back to sleep as a stranger who’d arrived after he’d been put to bed. When his mom got back and I told her this, she seemed stunned. “We’re kind of the same size, so maybe he thought I was you?” I suggested, not realizing at all how it might sound. Eight years later, a babysitter my 2-year-old had never met told me the same, that my daughter had woken up but she’d been able to get her back to sleep. Now it was my turn to feel shock, a tinge of excitement (could we go out more?), and some sadness.

With one Tribeca washer-dryer family, the mother disappeared into the exposed-brick bedroom as soon as she got home, reemerging with money to pay me. Back then, having cash on-hand in your house seemed like the height of adulthood to me. These days, I keep an envelope stuffed with bills in my underwear drawer, for emergencies; most of the time, I raid it for personal ones (like not wanting to stop off at the ATM).

I adapted other ideas from these families: The first time my daughter pooped on the potty, I went in for the wipe and heard myself saying, “Touch your toes!” — something I realized I’d overheard a mom tell her preschooler to do a decade before. And in a marriage that I consider egalitarian, I’m the one who arranges, greets, and pays the sitters, performing this weird dance that I learned in my 20s. It turns out I’m still working under some John Cheever–inspired assumption that it’s strange for a husband to text a younger woman to ask if she’s free, to welcome her into his house, to give her money at the end of the night.

Toward the end of the time we were living in New York City, I took my daughter to the Children’s Museum on the Upper West Side and realized that a woman stalled outside with her own kids looked familiar. She had an older child and was pushing a younger one in a stroller, and I realized that it was the woman whose 15-month-old I’d babysat eight years before, the one I’d rocked back to sleep and about which I’d said, “Maybe he thought I was you?” He was old (like 9), and he had a sister now, so it was his mom I recognized, a woman with mid-length brown hair who’d once stood before me in a green dress, no shoes on yet, and handed me a Post-it with WD-50’s number. I realized we were, in fact, around the corner from their apartment.

Our children were holding both of us up, so I didn’t say anything to her. Maybe I should have, but what? “Hello, I recognized your face! I’ve been in your apartment! I ate your cookies! Your baby, I held him in the dark!” Maybe it was a small gift: I was already stunned by how much time had passed, why remind her too? Or maybe it would have been strange because we’d never really known each other anyway. Separately, we herded our children along.

What I Remember About the Moms Who Paid Me to Babysit