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As a mom to a kindergartener, it’s kind of like I started real school this year, too. And I have a lot to learn. About arriving before the first bell. About how to find the main office and the nurse. About how to organize the stacks of paperwork that travel back and forth in my daughter’s folder.

And about the drop-off playdate. That one caught me off guard.

When school started, my sometimes-shy daughter seemed slow to make new friends. When I asked about her day, she told me that at recess she spent the whole time waiting to play with the girl who had been her best friend last year in pre-k, but her turn never came. Ouch. So I decided to organize some playdates for her outside of school. Maybe I’d make a new friend, too!

At the kindergarten drop off, I stalked one particularly friendly mom. Sloane liked her kid, I liked her. We exchanged contact info. It was all too perfect.

Until we started emailing about a playdate. And her note read: “I can pick up after school, and then the kids can play while I go run errands. Our nanny will be at the house. Feel free to pick up anytime after 4:30.”

Oh. This was a drop-off playdate. And I wasn’t invited.

After nursing my pride (aka getting over myself), I realized this could be the beginning of a great new era. I didn’t have to be there! I could do something else with my time, like get a haircut, go for a run, or take care of all those other kids I have. And Sloane could gain a bit more independence without Mama Bear around.

But wait a second. What did I really know about this mom? (Besides that she always looked effortlessly put-together at 7:55 a.m.) What did I know about their nanny? And what did I know about their home? Nothing. Absolutely nothing. I didn’t know whether they kept guns in the house. Whether they have medications in easy-to-reach places. Or whether someone with an abuse problem was living with them.

So at the risk of seeming like a helicopter parent, I emailed back: “Sounds great. Do you mind if I walk with you guys after school and get Sloane settled before heading out? I’ll just stay for a few minutes.”

Of course, she kindly obliged (probably realizing that I was a rookie parent to a school-aged child, while she had been through this twice before with her older kids), and I became the fourth wheel to the play date. Which ended up being a good thing. I got to chat with the mom, and we continued to hit it off. I was able to take a look inside their (beautiful) house, and while I didn’t exactly snoop, I felt comfortable that there were no red flags. I met the nanny, a very nice older woman. And when I peeked in at Sloane to say goodbye, she was having so much fun she practically shooed me away. Which made me happy.

But as I set off solo, I pondered whether I should have taken my inquiry into Sloane’s safety a bit further. I didn’t ask about the guns. Or the medications. Or if anyone else was living in the house. I just went with my gut that this house — and this family — seemed safe. I’m trusting this mom. And this nanny. And I’m trusting Sloane to use good judgment and stay safe. Was that the best I could do? Or was it simply as far as I was willing to go?

Tell me — because I’m still pretty conflicted — what would you do?

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Jessie Keppeler
A Maine native, Jessie migrated down the coast to Boston after college, and it’s been home ever since. She has lived in various corners of the city — from Allston and Brighton to Newbury Street and then Jamaica Plain — before settling in Brookline with her husband and three daughters. As much as she loves home now, she also likes to leave occasionally: recent family travels include Italy, Belize, and Washington D.C. Jessie writes with a cat curled up nearby and a dog at her feet. And a cup of coffee. Always.