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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
When your gut is saying "This is not quite right, somehow," it's really not quite right.
You're not going to believe me when I tell you that for two full days after the Boston fiasco, I left this babysitter on the calendar for the coming Wednesday night. Why? I felt stuck. I had to be somewhere for work. Dan had to be somewhere for work. To cancel on her made me squeamish. And there's this part of me (a part of me I don't really admire) that goes back to the laissez-faire, '70s parenting I grew up with. Part of me wants to be the "it'll be fine" parent, because I turned out okay, right? But I'm not that parent. And this isn't the '70s. So, on Tuesday night, with a big gulp, I called the babysitter and let her go. Then Dan and I adjusted our calendars.

Knowing you will never be the groovy parent will help you both.
Speaking of the '70s, I think that sometimes as parents we want to be groovier than we know we should be. It's hard to say to someone, "No, you may not have a beer after my child goes to sleep," because, let's face it, what mom among us has not had a beer after we've put our children to sleep? But here's the big difference: You're paying this person hard-earned cash to be, if not you at your superwoman best, then the soberest approximation of you that good money can buy. So, when you come home and there's a beer bottle on the counter, buck up, because you've got an un-groovy conversation coming your way.

It's rough out there in the global financial crisis, and it's okay to look for deals on laundry soap and string cheese, but don't go looking for a deal on a babysitter.
Here's one thing I've decided: I'll never pay a babysitter less than I'd hire someone to work for me as an assistant. Don't get the wrong idea—it's not that I often have assistants (I think the last time was prerecession '07!). But from time to time, in luckier days, when I've been working on a big project, I've hired a kid from the university. And whatever I paid them is what I expect to pay a sitter. Babysitting, I figure, is a job I need well done, because my child is precious. And short of adopting a nonworking grandma (a rare thing these days), no matter how tight money gets, I need every check I sign to say "I value you."

If you can't get a super sitter, you need a can-do babysitter.
Last fall, in the wake of the Boston debacle, my friend Celine said something important to me: "You need someone who makes your life easier." A lightbulb went on over my head. Here I'd been cooking up gluten-free meals for sitters, telling them, "Don't worry about the dishes," and ignoring the days when I came home to pandemonium. Suddenly, a door was opened. If I couldn't find someone whose tune was that song from Annie Get Your Gun, "Anything you can do, I can do better," then I needed something close.

Age matters.
Back when I was growing up, most babysitters were in high school. Since I've become a mother (this seems to be a cultural shift), my babysitters have all been young women in their 20s or early 30s. I think it's important to realize that if you have a 16-year-old sitter, she should be used only on weekend nights, and you should come home early—after all, she too is growing and learning. With someone a bit older, for whom this is a real-life job, you can ask for more. On the other end of the spectrum, if you're renting a grandma, be aware that she might not be able to stay until 2 a.m.

Know when to let go, or as my mother always says, "The only thing certain about the world is change."
When you finally find that perfect babysitter, the one your children squeal about when they find out she's coming over, the one who actually doesn't think it's insane to do the dinner dishes and put the toys away at the end of the night, the babysitter who is happily reading her book on the couch (not feverishly texting her boyfriend) when you come through the door and welcomes you with a smile, you have to accept that this person will someday, probably, need to leave you. She'll have to go to college or she'll have her own baby or just plain complicated life will take her away. And although you'll need to get back on the merry-go-round to find someone new, and probably suffer a few duds in the process, let her go. Bless her, thank her, and send her on her way. Why? Because holding tight when she wants to go isn't paying her the respect she deserves. Keep your chin up—there's a fabulous babysitter out there, one who needs a job and wants to do it well, and she's just waiting for you to find her.

Caitlin Shetterly is the author of Made for You and Me: Going West, Going Broke, Finding Home (Voice).

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