
Last Monday, 14-year-old Toby woke up in a bad mood. Dreading a long week of school, he thought about what might make him feel better. So, he sent a text…
“Hey, want to go to dinner tonight?” he asked my friend Leah.
For the past four years, she, Toby, and her daughter, Sydney, have gone out to dinner once every season. They all love the ritual so much.
Their very first dinner was in 2021, when I had Covid. “How can I help?” Leah had texted me, earlier that day. I’d told her that Anton was happy mucking around at home, but Toby was restless — he kept knocking on my bedroom door, lamenting that I couldn’t let him in — so could she ever take him out for pizza? Within an hour, she was at our door.
The evening went beautifully. Whenever Toby loves an activity, he immediately declares it “a tradition,” in hopes that it will happen again. And this time, it worked. Leah became his neighborhood aunt.
The meal usually includes bread, pasta, Shirley Temples or ginger ale, and dessert. “It’s called ‘Auntie Rules,’” Leah laughed. “The rule is, they can get whatever they want.”
“At first, we’ll start off being silly,” Leah told me. “We’ll play Heads Up or I Spy. But during the last 20 minutes or so, Toby usually starts asking questions and opening up, and then I’ll hand my daughter my phone, so he and I can talk.”
Anton is always invited, but he likes to stay home for some quiet time. “Now instead of trying to convince him to come, I bring him a treat,” Leah told me. “Like, s’mores pizza or a yo-yo.”
I’m enormously grateful that Toby and Anton have a trusted adult — outside the family — who roots for them and is always there for them. “A relationship with a teenager is special,” Leah told me on the phone. “Over the years, we have talked about your divorce, his friends, girl stuff, school stuff, all kinds of things.” She pauses, then adds, “I envision this friendship for life.”
P.S. How to be a neighborhood aunt, baby version, and 10 things I love about parenting teens/preteens.