My Boss, My Best Friend. By Lauren Hoffman.'s Nanny Issue.

We sit on the couch, pasta carbonara precariously balancing on our laps, twin wine glasses perspiring as their contents turn tepid. Some Kind of Wonderful plays on the television, and though we’ll comment on Mary Stuart Masterson’s unfortunate hairstyle, it’s mostly background noise. Before the night is out, we’ll set the Tivo for Top Chef and debate whether breaking up with someone over the phone is ever acceptable. When we say good night, I’ll ask, “Ten tomorrow?” 

If we were friends parting ways after a girls’ night in, making plans for morning coffee, this exchange would pass for normal. But Lisa is my boss. I’m nanny to her two sons, Henry and Max, and come ten in the morning, I’m back on the clock.

Lisa and I had a decent rapport going from the day I started working with the family over two years ago, but now we’re as close as sisters. When you see someone knocked flat by morning sickness and ebullient at the sight of the first story her child dictates; when you are both literally shat on by the same child in the same day, you bond. I always come up short when my friends pump me for stories of the Upper West Side ice queen they presume my boss to be. I shrug, “Well, I like her.”

This summer, we’ve grown even closer. After a day of being Beach House Nanny Barbie at the summer rental in Connecticut, I’m usually reluctant to schlep back to Manhattan just to turn around the next morning and come back. This means that most late afternoons, Henry turns to me like a miniature Lothario and says, “You gon’ sleep at my house?” I am, although I often don’t sleep all that much, because once the boys are tucked away, Lisa and I exist together in an endless state of sleepover. Topless pillow fights and hair braiding are absent, but we talk in a way I don’t talk to anyone else. She’s seen me cry and she’s seen me in my retainers and face cream and she’s seen me in a snit, and she’s still there. When I hear employers say “Oh, our nanny’s just like a member of the family,” I smile and nod and internally call bullshit, but for me that’s true.

“Love whoever you want,” a friend warned me. “But at the end of the day, it’s just a job. If they stopped paying you, you wouldn’t still be there.” In fact, Lisa did let me go last fall, just after her second son was born, when she needed more hours covered than my graduate coursework would allow. I found a new job, but I still popped in and out of her household to play with the boys and spent hours on the phone with her. I was back to work for the family within six weeks. Lisa now endures endless teasing about the time she tried to fire me and it didn’t take.

I know our situation isn’t normal. When asked at my next job interview, “How do you see your relationship with me as a parent?” I’m certainly not going to answer, “Well, I thought it’d be nice if maybe some days we decided it was too hot to do anything but shop, so we took the kids to Anthropologie and I let the baby play with my flip flops while we tried on sundresses? Then later, when the kids are asleep, we could get sloshed. Sound workable?” Which is really too bad. When I think about future jobs, I’m saddened to realize that any negotiations about salary and sick days probably won’t take place while watching bad movies and making S’mores in the broiler.