In Which Toby Goes on a Date

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 and pick-me-up. 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.

  1. Nicole says...

    This is without a doubt the sweetest thing I’ve come across in quite some time. I could feel his excitement! Thanks for sharing.

  2. Lorenna Rodrigues says...

    How cute!!! My 5 yo daughter loves to eat at fancy restaurants, especially if its foreign food, she’s always in her best behaviour, its adorable!

  3. Sarah says...

    I just love that first picture. Such a little man.

  4. Kammy says...

    I used to read your blog before and I just found it again today. This post just made my heart melt! Too cute!!

  5. Elizabeth says...

    I’m a bit late to seeing this…This warms my heart almost bringing me to tears this is so sweet. Thank you for sharing.

  6. Tori says...

    Long time reader and its always a pleasure reading your posts. I have to say this is definitely one of my favorites. Your son is so, so sweet. I’m pregnant with a little girl right now and was a little relieved to find out we’re having a girl thinking it be easier to bond with her but reading about your sweet, sensitive son makes me so excited for potentially having a son as well. Wishing you all, all the very best.

  7. This is the sweetest! I love the picts. Can’t wait to do this with my lil boy one day

  8. Haha this is just the cutest thing! And the way that you’re looking at him across the table in that one photo is just the sweetest, you have such love for him in your eyes! <3

  9. this is just the sweetest freaking thing!!

  10. Jo, this felt almost like a TV episode, I hung on to every word. So damn sweet.

  11. What a great idea! Love this. Toby is the sweetest!

  12. EJ says...

    I love your family. I think I am as old as you and married too …but no baby yet… I wish I had a son like Toby. He is so adorable and quite interesting! Like in the video once you shared with us! Toby dancing to some music topless!

  13. this is so sweet!

  14. I laughed the while time I was reading this! How adorable :)

  15. Ooooohhhhh….melt. What a cute post. That sweet little guy sitting in a ‘fancy’ restaurant. This makes my day.

  16. This is the cutest idea ever!!