Tonight I’m letting my son Nick and his best friend, Max, go to a Yankees game by themselves for the first time. This involves an hour-long train ride from our hometown to the Yankee Stadium stop in the Bronx; then they’ll have to walk about eight blocks to the actual stadium, find their way to their seats, buy themselves dinner and, most important, keep in touch with my husband and me so we can find them in the massive crowd when we come to pick them up (we aren’t quite ready to let them navigate the late-night commute home). In all, they’ll be on their own for about six hours—though, of course, among 50,000+ other fans they won’t technically be alone. I’m nervous, but I know that as smart, sensible, newly minted 14-year-olds Nick and Max need to begin experiencing independence. In fact, Nick got the idea to go to the game sans parents from Executive Editor Darcy Jacobs’ son Matthew. Here’s her story:

I hope Nick and Max get as much out of their solo adventure as Matthew did—that will give me more confidence to okay future unsupervised outings. Wondering if your child is ready to handle a bit more freedom? Read “Benefits of Free-Range Parenting," from our July issue, for more anecdotes and expert advice.

Have you had a similar experience with your kid? Please share in the comments below.

Linda Fears is editor in chief of Family Circle magazine.