For the past year, four-year-old Toby (a hopeless romantic) has been very curious about what it’s like on a grown-up date. “What do you do?” he asks us. “Where do you go?” Our explanations have never satisfied him, so this weekend, we decided that he should dress up and come see for himself…

We got a babysitter for just Anton, which pleased Toby to no end. All day he gleefully kept telling baby Anton, “I’m sorry, Anton, but I can’t play with you tonight,” and “We have to tell our babysitter that it’s ONE kid, not two.” (Anton could not have cared less.) Then Toby dressed up in a sports jacket, sweatpants and sneakers (as one does), and more or less ran the whole way the restaurant.

We chose a neighborhood Italian restaurant, Marco Polo, which feels theatrical (tea lights, waiters with ties, salads mixed at the table) in a way we knew would thrill Toby. “The vibe tilts perilously close to high kitsch,” says New York Magazine, and as Alex jokes, “It’s perfect for both people in their 80s and four-year-olds.”

As we walked in, Toby gazed around with wide eyes, and whispered, “It’s like a wedding.” The sweet waiters treated the event with great fanfare—presenting him with a menu and unfolding his napkin for him. “Would you like a special drink?” our waiter asked. “Yes, please,” Toby replied. “Orange juice.”

We ordered their signature red wine fettucini which is mixed tableside in a parmesan cheese rind (!).

It was decadent and delicious…

…although Toby instead ended up eating the entire bread basket, plus a chocolate mousse. No rules tonight!

It was a really fun night. Thanks for joining us, Toby! I hope it was everything you had ever dreamed of! xo

P.S. Conversations with a four-year-old, and the Cup of Jo Guide to NYC.