Every fall, I cull a fresh round of babysitters like a bushel of crisp, peppy apples to pluck from throughout the school year. Most of my child minders are students whose availability waxes and wanes as often as my needs. I’m always looking for a new sitter, just in case—you never know when someone’s grandfather will fall ill or someone else’s roommate will borrow and crash her car.

Admittedly, I’ve become somewhat cavalier in my selection process—I once approached a swarm of teenagers in a coffee shop to ask if anyone would babysit my children, one of whom stood nearby, clutching his chocolate milk so tightly that it surged like a leaking garden sprayer, trickling down his forearm. (They said no.)

More recently, I asked a camp counselor named Margaret if she would babysit my kids one evening—night time sitting is always good for a trial run. She said yes.

“Great!” I nearly squirted in reply. That part was over.

Then the fretful waiting period began. I wasn’t sure whether Margaret could actually handle my toddler. Would she swat angrily at the dog when he stuck his nose in her crotch to say hello? I imagined my older children bickering over coveted Lego pirate pieces like the peg leg or the pot of gold while Margaret, bemoaning her bad luck, erased my contact number from her phone before she’d seen what I was willing to pay her. Amidst all this fantasy of flop, I grew annoyed at my children for not always being perfect little people.

I often wonder whether training a sitter squad actually adds to my family’s stress rather than relieving it.

My mother never had this problem. She and my stepfather married and created one of the very first Brady Bunch-style blended families of the early 1980s, or so we boasted when asked. My grandmother took one look at my mother’s new pride of five children, ages newborn to 13 with various last names and even more afterschool activities, and declared that my mother needed help.

The way I remember it, one sunny morning when I was still in my nightgown—an older brother’s borrowed t-shirt that hung down to my knees—my grandparents showed up in our driveway trailing a young woman named Mavis from Bequia, a tiny island in the Grenadines, whom they had sponsored to work in the U.S. as our live-in babysitter.

Mavis talked about earning her green card, which I imagined was a sparkling slice of plastic that she’d carry in her wallet like an American Express—I wanted one, too. While Mavis was busy trying to follow my mother’s rules, we were figuring out how to get her to break them. On weeknights when my mother was out, Mavis let us watch forbidden sitcoms, the foundation of our pop-culture education. Mavis would flush any cold, picked-at portions of my mother’s abominable beef stew into the garbage disposal without lecture. We adored her. Eventually, after nearly 10 years, Mavis became so giving toward us that my mother felt she and Mavis were working against each other, as though Mavis herself had become one of the children. When their relationship fell apart, my sister and I were devastated.

In the absence of extra square footage or time available to incorporate a live-in sitter into my family life, and as a freelancer with a somewhat unpredictable schedule, I piece together my childcare needs like intricate quilting blocks.

Truthfully, much of the stress involved in choosing new babysitters comes from my own desire for my children to be as lovable to their caregivers as they are to me. But I don’t hire babysitters to replace me. I hire them to cover for me when I have other work to do. I hire them to bring a little whimsy to interactions with my kids, especially when the boys are bored and clobbering our old, gassy dog with foam swords.

Sometimes, a little variety is best.

Ten minutes before Margaret was to arrive for the first time, she texted me. I griped out loud to my handbag, which I’d already slung over my shoulder, convinced that Margaret would be a last-minute canceler.

Instead, she had a question:

“Do you have sugar and cocoa powder? I was thinking I’d do a baking project with the kids. Chocolate banana sorbet.”

I yelped in relief. My husband and I laughed, wondering how our daughter would fare—she is our freestyle baker with no knowledge of chemistry or basic clean up skills. Normally, she turns our kitchen into a celiac-detonating test lab with her freakishly flat gluten bombs that require cooking tools in the shape of, say, crowbars to release them from whatever sorry pans brought them to life.

Yet here we had a babysitter, ready and willing to engage all of our kids in some kind of bona fide goodie project with an edible result—now that was going to be a real treat.

“Yes! They’ll love you forever,” I texted Margaret in reply.

By the time my husband and I returned home from dinner out, the kids’ sorbet was back in the freezer with four frostbitten spoons sticking out of the mixing bowl like cattails in a wintering marsh. The sorbet looked downright icky—I couldn’t tell the finished product from the spills all over the countertops or the cocoa-colored mustache dried beneath my dog’s nose.

So much for waiting for dessert until we got home, I thought. Also, I’d forgotten to ask Margaret to help me clean up the kitchen—having multiple caregivers means there’s always a lot of information to pass off before I can be on my way.

“They were great,” Margaret said of our kids, “I’m around all year if you need me.”

I emptied my wallet and turned the change jar upside down, searching for quarters to round off her pay.

The next morning, our kids wobbled groggily downstairs.

“Did you guys try our chocolate sorbet?” our older son asked, rubbing his eyes.

“Yes!” I lied.

The kids looked at each other proudly and smiled.

Our daughter turned pensive.

“Mom, I think Margaret is my favorite babysitter we’ve ever had.”

That settled it. My children may not be developing the same type of bond with one particular caregiver the way that I did, but for them, meeting the new sitter never gets old.

Samantha Shanley is a freelance writer, editor, and mother of three. She blogs about parenting at Simtasia. Follow her on Twitter @SimShanley.

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