Dates With Your Child

For his fourth birthday, Toby got what he had always wanted: A sports jacket. When he opened the box, his eyes lit up. Gold buttons! Lapels! POCKETS! It made him look just like Daddy and will come in handy should he get married this year.

To celebrate, we planned a date. We have gone on a few mama/son dates lately—a tradition we had years ago that was put on hiatus after Anton was born. It’s so, so nice to have some time alone to chat and laugh and follow his lead and go exactly at his speed (for example, taking detours to climb every single step/rock/curb/ramp/incline on the way to the restaurant).

During dinner, as we wait patiently (it’s hard to wait!) for the food to arrive, Toby always asks for stories about before he was born. So last night, over burgers at Shake Shack, I told him how I met Alex and how we went to the movies and how we got married and how we had a sweet sweet baby. “And do you know what we named our baby?” I asked. “No,” he whispered, eyes wide as saucers. “Toby,” I told him. Mind. Blown.

Here is Toby telling me how he met Dun Dun, his beloved imaginary friend. (On a boat in Holland, it turns out.)

It was such a sweet evening and reminded me how nice it is to carve out one-on-one time for people you love. It’s such a different pleasure from being in a group! (Also, didn’t you love asking your parents about when they were younger? I remember that so distinctly.)

P.S. A three-year-old in conversation, and an awesome trick for grown-up dates.

  1. uhhh so cute >,<

  2. wow your son look so cute. when he is adult, he will be handsome.

  3. This is the sweetest! What a lovely tradition. He will treasure this time with you forever (and more and more as he grows up), I am sure!

  4. Joanna-
    When I look at these photos of your beautiful son, I think that he has a quiet, rooted confidence and a gentle joy that comes from being well loved by his parents.

    Darling story. Blessings.

  5. So sweet. Happy Birthday,Toby! I can’t believe he’s 4. I’ve been reading your blog since before he was born! Since T loves stories and probably stories that involve himself (after all we all do at any age), have you told him or started to explain that he’s a little bit famous? In that all your readers know about him. I’m just thinking about how his birth story joyfully blows his mind? Explain to a 4yo that a lot of people know who he is. I can’t begin to imagine what little minds think of the internet. It’s all they’ll ever know but still…

  6. Wow, I’m so surprised with myself that I’ve never thought about dates with my girls! Mine are 3 & 4, together they feed off each other and going out (even grocery shopping!) isn’t a super time. I’m always so busy mothering, errand running, nursing schooling, cleaning! And lately I’ve been looking at my kids and think, you look older all the sudden! :( Don’t we all wish they would stay small. I love this idea, I love your site. Thank you so much <3 Beth in Alabama <3

  7. I just did a date with my 7 year old and could not have had more fun! I pulled him out of school (shhhh!) and we went and got authentic Italian pizza and saw maleficient. It was the best day :)

  8. Beautiful story, Joanna. He looks so adorable in his jacket!

    Your dress is beautiful, also.

  9. This is precious. That jacket is the cutest and so is he. One-on-one time is so important. I love that you two had this.

    Came to visit from Kristin’s blog, Two Cannoli! :)

  10. I completely see what you mean in past posts when you’ve said that he’s an old soul. The way he is with his little brother, the way he wonders about life before he was there, such a romantic! Congrats on the beautiful family you and Alex have!

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  12. How freaking precious is this?!

  13. Posts like these make me so excited for 2 years from now. My little dude will be 2 next week and he’s already such a funny character, he has us cracking up all day. But a sports jacket?! Big heart eyed emoji! Our son loves fadoras, just like his other mama. We’ll be heading out the door and he’ll come running back inside yelling “hat!” and he’ll run to get one. I could eat him up.

  14. Every time you post a photo of Toby, he’s got a new bandage on. LOL. It makes me go, “aww, poor guy,” but I also can’t help how endearing it is. =)

  15. Killin me with cuteness! I love these family posts!!

  16. This reminded me of when my kids were younger and in school. I would surprise one of them at a time by picking them up from school and taking them to lunch. They each got a surprise “mom and me” lunch date at least once each school year. The loved the surprise of it and it gave me a chance to spend special time with them. Great memories!

  17. This reminded me of when my kids were younger and in school. I would surprise one of them at a time by picking them up from school and taking them to lunch. They each got a surprise “mom and me” lunch date at least once each school year. The loved the surprise of it and it gave me a chance to spend special time with them. Great memories!

  18. How is Toby’s violin playing going or was it a passing obsession? He’d look great with the violin and the jacket, a real professional musician!

  19. your raising a fantastic bright and sensitive young men. bravo !

  20. your raising a fantastic bright and sensitive young men. bravo !

  21. I just love watching Toby grow up. Such a sweetie. Thanks for giving us peeks in to your life xo

  22. Toby has the most hilarious sense of humor I’v ever encountered in a child (and I’m a preschool teacher!) Meeting his imaginary friend on a boat in Holland just about takes the cake!

  23. dc says...

    He is so adorable! We were a group of 14 for dinner last night and passed another adorable 5 month old named Darwin around our circle of friends. Those of us with grown “babies” miss these early stages so much. Enjoy!!

  24. How cute is he? Love this idea!

  25. You are such an amazing momma to him. Toby posts will forever be my favorite, he is growing up to be such a cool dude.

    xxoxoxo Dakota

  26. This is so heartwarming.

  27. Absolutely adorable!!

  28. I want to go on a date with Toby!! He is the most sweetest, loving boy on the planet! Joanna, you and the hubs are doing such an amazing job raising your two little nuggets. I hope to be just as awesome a parent when my time comes!

  29. Toby is so cute. I love it. This makes me look forward to having kids!

  30. I think Toby is possibly the best kid ever! You are so lucky to have him!

    I love having dates with my 3 year old son.

    Last month, on a sunny sunday morning (my husband was working, the poor guy!) we went to the Lisbon Oceanário, wich is the biggest aquarium in Europe (it has sharks, pinguins, sting rays, turtles, all kinds of fish from all oceans and seas)and we had a blast. After, we went for a burger lunch in a very trendy spot in town. When we arrived home he draw the pinguins and the snow (the favorite thing he saw in the aquarium) to show to dad.

    He still talks about it today.

    And I love this dates…

    PS – my son wore much more casual outfit (a black leather jacket that it loves!!):-DDD
    Toby’s jacket is just adorable, i have to say!!! A real gentleman

  32. I always go on dates with my son.This is my most favorite thing in the world!

  33. This is so sweet. I took my daughter to swimming, for a haircut, on errands and out to eat this week as a special day with just her – no baby! I agree, so nice to just go at their speed. Also, sad that in the background of the photos there are so many people on their phones! Makes you try to remember to put it down once and a while – well done for enjoying your time with him :)

  34. Toby is too cute!

    I’m finding that my 5-year-old needs a lot of one on one time. I took her out for a smoothie last Sunday and I let her talk and talk and talk. No distractions, just me sitting across from her and listening. I didn’t have to say much at all really, she just wanted an ear. It was really nice. I’m hoping she remembers our dates as she grows older. They’re incredibly special to me and I hope they are for her.

  35. What a great post. I love the jacket! Would you mind sharing where you got it from?

  36. This is such a sweet post!

  37. My mom took me on a birthday date after my fourth birthday–it became a tradition. We had dinner at a Chinese restaurant and I felt so grown-up sharing a pot of tea with her. Afterwards, she took me to an orchestra concert and I was fascinated by the violin soloist. (The Duplo block figure with the green dress became my favorite, because that’s what the soloist wore). I insisted on staying after intermission and begged my parents to let me play the violin for two years, until I started after my sixth birthday.

  38. Toby is not to be believed! He is so, so cute. I love his request for a sports jacket and some stories before his time. His genuine curiosity is beyond endearing.

    What a sweet date : )

  39. I love that his imaginary friend is named Dun Dun! My daughter had one named Megawonks! Now if we bring it up she thinks it’s the craziest thing (she’s 7 now). Ps-wouldn’t it be adorable to get Toby a corsage for his coat??

  40. What great pictures. As a single parent with an only child we are together all the time :) but sometimes its nice to stop. Sit. Talk. We have a busy life and rarely sit down together to eat focusing just on each other. So I try to remember to do that every once in awhile – no phones, or electronics – just me and him sitting and talking. And he does love hearing about himself, stories of when he was younger. I created a wooden egg story of when we got his dog – I drew pictures on it. And even though he mouths the words as I say them he wants ME to tell it…and then you said, I want this one but that was a girl and you had to pick a boy and then one came and st on your lap and you said this one this one and on the drive home he tried to push you out of your car seat (and he laughs and laughs)

  41. It is my favorite blog post EVER!!!!! Made me well up with tears. So gorgeous!

  42. This may be my favourite blog post. Ever. So sweet!

  43. Stop it! He is too precious and can marry my 3.5 yo, wedding obsessed daughter, ha. I always am happy to hear when the opposite gender has similar obsessions!

  44. this post made my heart expand!! and his little outfit is just too cute!

  45. I LOVE when people that their kids on dates, it’s so special!
    It helps he’s such an absolute cutie

  46. We take our kids on dates too. They are so pleasant out alone. One time I took my oldest for ice cream and then we read books at the bookstore and on the way home he said it was an awesome time!

  47. Ohmygosh, he’s so gorgeous. What a sweetheart!

  48. aaww this is so sweet! I love the idea

  49. I hope we’re all on the guest list for what is sure to be the wedding of the year! :)

  50. Such a great idea! Toby is a total ladykiller in that coat, too!

  51. LOLing right now! Who knew a jacket accompanied with a bandaid could look so good.

  52. HY says...

    I love your posts about Toby, he sounds like such a cool little guy. These mama/son dates are a wonderful idea!

  53. This is so sweet. I know what you mean about asking your parents about when they were younger. I loved loved loved my mother’s stories of her wacky dormmates at NYU in the 70s, prancing around Greenwich Village (the stories always involved very rich girls who had no idea how to do laundry, which amused my working-class mother, who earned extra money in middle school making beds in a boarding house). That and I loved hearing the crazy stories about all my dad’s college friends who got arrested for being drunk and disorderly while going to school in a dry county in Tennessee. He claims he was never arrested himself…

  54. I love Toby posts! He’s got such a personality on him. How does a 4 year old even know what Holland is? Love it.

    Dearest Darling

  55. Joanna, I really love your writing. It is always so heartwarming, thanks for sharing. x

  56. His face in the second picture is fantastic!

    I love this…I used to go on dates with my dad as a little girl and even into college (I still do whenever I visit him). I always cherished those times.

    My husband and I are expecting our first and have already talked about doing that with our kids. I just think it’s such a great tradition to have!

    Thanks for sharing, Joanna..your family really is so cute :)

  57. Oh my goodness…how sweet! And he looks so dapper in his sport coat. Such a cutie!

  58. Whoa…in the close-ups, the sport coat really makes Toby look like Pete Campbell!

  59. This post (story) made my day. The absolute cutest photos of Toby to go with it! Thank you for sharing. xo.

  60. OMG, cutest little fella ever! Next to my cute fella of course. I really enjoyed this blog post – I too have dates with my son, and I love them! We have great talks, he is an amazing companion and I always learn something new and interesting about him.

  61. I’ve been reading your blog for at least five years, and this is my favorite post by far! Loving that jacket.

  62. That was so cute. The part about you telling him about naming your sweet baby “Toby” and his mind getting blown made me laugh.

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  64. Oh my word! I was gushing over him in his little sports jacket, (so handsome!) and then that story about telling him what you named your first baby! Thanks for making me smile today. This makes me excited to have kids someday = ).

  65. My daughter (11) and I celebrate “girls’ night” every Friday night, usually with a movie and popcorn, but we’ve also gone to a play, gone to dinner and even given each other mani-pedicures! We’re very close, and beginning this spring my son (6) and I have begun Saturday afternoon dates. It’s so special to spend one-on-one time with these little creatures, they grow so fast.

  66. That bandaid just totally completes his little boy outfit! So cute that you gave him a sports jacket :) He looks very dapper.

  67. oh my holy sweetness. could Toby be any more adorable than he already is?? I love that he wanted a sports jacket! That sweet little man!!! You are so very lucky to have 2 boys. I raised twin boys and those early years were nothing short of pure heaven. seeing the world through their eyes was the most amazing experience. It goes by so quickly – don’t you wish you could make it last a little bit longer?

  68. This is just so adorable. I love the idea of a mother/son date at Shake Shack and I can’t believe he asked for a sports jacket!

  69. Looks so handsome in that grownup jacket. BUT the very best part of the outfit is that band-aide peeking out through his hair. Love toddlers!!

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  71. this post made me laugh out loud. oh toby. i love that he wanted a sports jacket!

  72. Toby is the sweetest little boy!

  73. My dad took me on dates for years when I was growing up. My parents have all the adorable pictures of us together. Two things happened on every date. One is that I always got to pick out my dads outfit and the other is that we always went to Steak n’ Shake for a large chocolate milk shake and we’d share it on the way home. The night before I got married, we went for one more ride to Steak n’ Shake for one last chocolate shake. Keep up the dates Joanna, they make great memories for you both!

  74. Aww so adorable! Little boys just look so cute in blazers. I bought my 8 year old a Summer blazer from J Crew and he loves looking like his dad. Love how you describe the date, it’s so wonderful to chat and bond. I love doing that with my son when we walk to and from school.

  75. MM, wow, that is nuts. and amy, your little one sounds adorable!

  76. jennifer, yes!!!! he would be thrilled!!! hahaha

  77. michele, oh yes! he fell down some steps at the playground. it was a pretty big scrape, poor thing! he’s always getting bumps and bruises, the fate of a 4-year-old i guess….

  78. I distinctly remember saying “tell it again!” after my mom would finish a story when I was young.

    My a favorite was the story about how she found a purse on her way to work, and when she opened it to find an ID card, all that was inside was a gun, and then she called the police and they came to get it. The end. “Tell it again!”

  79. This is SO sweet! I can’t believe he wanted a sports coat, what a cool guy! I love that he has his own style and that you encourage it. My little son is 14 months so he’s not quite the conversational dinner companion yet but I’m looking forward to dates with him soon! Love this.

  80. He’s just too sweet! I love that he wanted a sports coat. Most tiny people wouldn’t even know what one was!

    I used to take the kids I nannied on ice cream dates. The little boy always want to go for ‘chocolate and vanilla squirrels.’ Cracks me up to this day!

  81. Love this! When we were little (I’m one of four kids), my dad took us on “time only” so we got one-on-time with him. Such amazing memories. My favorite thing was to go to bookstores. I will definitely be doing that with my kids one day!

  82. Toby is going to grow up to be such a dapper gentleman. Most boys don’t even know what a sports jacket is!

  83. Sports jacket + overalls + forehead bandaid = freaking adorable! I’d like a date with this little man ; )

  84. Oh, Joanna, this is why I love your blog. “Mind. Blown.” Ha! so cute… Toby stories are my favorite!

  85. Hi, there! LOVE your dress – would you mind sharing where it is from?

  86. I dream of dinner dates with my little guy (11 months) wearing a navy blazer one day. So incredibly sweet!

  87. Oh, Toby! You could not get any sweeter. And I smile every time I read about Dun Dun. Just the best.

  88. He is so so so adorable :) i love the idea of alone time with each child.

    i have the dame dress. It looks great on you. It makes me like it even more.

  89. Oh that melts my heart with all of the sweetness!

  90. I can’t even tell you how much I cherish the dates my mom would take me on! And my Mema! Even though I will miss my sisters while they live out of state, I’m very excited to get the chance to hang out with my parents again, just us!

  91. I’m so curious to see what happens when my boy is a little older. He’s not quite 2.5, and I don’t think he can quite process the idea that his parents had a life before him yet (I’m starting to lose touch with the idea myself!). But the idea of someday having this kind of conversation with him and his sister is so, so sweet.

    Toby is a doll. His parents must be awfully wonderful to raise such a sweetheart :)

  92. I’m in love with his sweet imagination!
    He seems like such a fun boy!!!

  93. Adorable! What a wonderful evening. I love the bandaid on his forehead. And then I happened to click on your post about the sports jacket and noticed the picture of him with a bandaid on his chin. I have bought more boxes of bandaids for my children in the last five years than I can count. Even when they don’t have a scrape, they want a bandaid!

  94. Just as I opened the page, my 3.5 year old daughter came over and asked, “who is that boy?” And I told her his name was Toby. “I kind of want to marry him” she says. And then, “Can we go find him?” :)

  95. What a sweet, sweet post.

  96. So dapper in his handsome jacket!
    Loved this post!!!

  97. Super cute!

    I so agree with you about the one-on-one time. My husband comes from a massive family and it seems like it’s always just one huge group of people celebrating 10 birthdays at once and all getting together en masse. It’s nice to have those celebrations, but I’m much more of a “let’s have dinner with one of them one night” type of person. I feel like the one-on-one interaction builds and strengthens different types of relationships. Same goes with children. I don’t have any of my own right now, but I agree that nurturing individual and group relationships is the way to go!

  98. I’ll be working at a preschool in Spain next year, and I’m overall terrified, but this adorable story of Toby reminded me of all the amazing moments that working with such young children will bring about :)

  99. SO cute. all of your posts about the adorable and hilarious things toby says make me so excited for motherhood!

  100. I always ask my parents for childhood stories and either they don’t remember or the story is so embellished that it evolves into multiple new stories. This generation of kids has cameras, videos, blogs and all kinds of social media cementing their childhood milestones, serving as a scrapbook when our memories fail us. Not sure if that’s for better or worse : )

  101. Oh this is just too sweet. Toby seems like a rad little dude.

  102. Oh this is just too sweet. Toby seems like a rad little dude.

  103. That’s a beautiful blue dress! Would you mind sharing where you got it?

  104. That jacket is adorable, but what happened to his forehead!