One Saturday night last fall, my husband, Dan, and I drove down to Boston from our home in Portland, Maine, for an evening out. We'd gotten a babysitter for our son—a 20-something woman who had watched him occasionally in the summer. She was not a super babysitter or a natural with kids, but she was fine. That night she came at the appointed time, and off we went.

After a long evening, as we drove back up I-95, my cell phone rang.

"Where are you?" the babysitter wanted to know.

"On our way home," I said. Convivially, I regaled her with the tale of how we'd gotten lost in Boston (I think everyone gets lost in Boston) and that we were running a little later than planned. She seemed appeased. Let's face it, when you're a babysitter and the parents are running late, you make more money, right?

Then, a little while later, the phone rang again. "He woke up," she said, sounding a little bit peeved.

I felt myself get tense. "Is he okay?"

"I think so," she said, willing me to fix this from the car.

"Well, can you get him a stack of stories and read to him, maybe get him a little water or juice in a bottle? And if all that fails…" (my confidence in her was shaky all of a sudden) "…he can watch some of that Dr. Seuss video, I guess…"

"Okay," she said and abruptly hung up.

When Dan and I finally slinked through the door, by then the clock reading well after midnight, we felt like teenagers who'd stayed out past curfew. Our son was still awake, zoned out to Seussical nonsense.

The babysitter jumped up, leaving with a hefty check but without so much as a "good night." It was clear: We were in trouble.

Over the next few days, I fretted. I felt ashamed that Dan and I had gotten lost in Boston, embarrassed that we'd been out together having fun.

But, wait; shouldn't she have been in trouble with us? Weren't we paying her to do a job? One that included getting our toddler back to sleep? Hadn't I told her, "We'll be very very late?" Didn't that one sentence allow me a few hours to let time slip away as it used to in my 20s?

I realized in that moment that maybe she was a pill—and also that maybe I was selfish to assume that "very late" meant the same thing to me as it did to her. Either way, it was clear I needed a solid checklist of reminders for handling the delicate relationship between parent and babysitter. As soon as I made this list, I felt less like I was being held hostage by my own sitter. I needed her, it was true, but not as much as I needed to be sure she was the right fit. Here are the notes to self I came up with:

Next: Six Ways to Have a Healthy Relationship with Your Babysitter


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