Right down our block is a gourmet deli, and we’ll often stop by for milk or a little treat. The owner, Wally, is wonderful and has tons of inside jokes with Toby and Anton—and once even let Toby come behind the counter, which was basically the highlight of his young life.

For the past four years, Toby has chatted up every grocery clerk, old lady sitting on a stoop, guy walking a dog, mail carrier…and don’t get him started with cab drivers! (“What’s your name?” “Are you a daddy?” “What kind of car is this?” “I LOVE NISSANS!”). I love his gregariousness and encourage him to strike up conversations. It makes New York feel like Sesame Street.

Drew Hoolhorst recently wrote a beautiful essay about expecting a child, and I liked this part:

Let’s tell him to hold the door open for every person, ever. To talk to the guy at the grocery store, because it’s fun. Let’s tell him to talk to strangers for the most part, because as long as they’re not in the back of a van strangers get a bad rap. They’re the joy of your life and you should talk to as many of them as possible.

I wholeheartedly agree, and I’m the same way. But as Toby gets older, now and again, I wonder, when should talk you talk to kids about stranger danger? And what should you say? The vast, vast majority of people are warmhearted, and I don’t want to make Toby nervous around strangers or quash his friendly spirit.

When we were growing up, my mom read us books like this. I also once read a tip (from a reader in the comments section, I think) to teach children that if they get lost, they should find a mom and ask her to help. That seems like a smart idea since it might be hard for little kids to figure out who is in a uniform and intimidating to approach someone so official and formal. And another friend actually writes her cell phone number on her kids’ arms when they’re in sports stadiums in case they get lost. Brilliant, right?

Do you let your kids talk to strangers? Have you read them any books or given them any instructions? I’ve been curious to ask you guys this for a while now!

Update: Read the comments! They are amazing! Totally worth it! Thanks so much to everyone who weighed in. xoxo

P.S. More do or don’ts, including tomboy perfumes and changing your name when you get married.

(Photo from my my Instagram)