Parenting Her Way: Kourtney Kardashian's Most Unforgettable Mom Moments

We're celebrating Kourtney Kardashian's journey as a mom, from her hands-on delivery of her firstborn son Mason--who's turning 10 today--to posing nude while pregnant with her third child, Reign

By Natalie Finn Dec 14, 2019 12:00 PMTags
Watch: Kourtney Kardashian's Mommy 101 Moments

Kourtney Kardashian has always been a hands-on mom.

Literally, in fact, right from the moment she took matters into her own hands 10 years ago and guided her firstborn son into the world—a scene later watched by 4.8 million Keeping Up With the Kardashian viewers. Hey, the doctor asked if she wanted to, and she did!

Today, that wee baby boy, Mason Disick, is celebrating his 10th birthday—no, thank you for asking, but we do not know where the time went—and that means Kourtney now has a decade of mommy memories behind her.

Mason, of course, was joined by sister Penelope in 2012 and brother and birthday twin Reign in 2014, and his circle of cousins has expanded to seven. But his birth is where the Kardashian baby boom all started, Kris Jenner's first grandchild and the first member of the next Kard generation.

"You teach me so much every single day and changed my universe the second I met you," Kourtney paid tribute to her son on his fifth birthday in 2014. "You have taught me what life is all about and I am truly blessed and honored to be your mommy."

Mason Disick's Fortnite-Themed Birthday Party

From his meme-able birth to his cowboy-themed 2nd birthday, to last year's Fortnite-themed festivities, getting to watch Mason grow up has been one of the biggest perks for devoted Kardashian fans. At the same time, over the past 10 years we've watched Kourtney come into her own as a mom, blazing a trail for her sisters and brother, juggling work and play, and figuring out the whole co-parenting thing with her kids' dad, Scott Disick.

It's been a journey for one and all, happily punctuated with all sorts of funny, sweet, harrowing and altogether memorable moments.

For starters, of course, there was the extremely calm lead-up to Mason's debut, when Kourtney—her water having broken—paused to finish her laundry, shower, shave her legs and put on some makeup before heading to the hospital.

Charley Gallay/Getty Images

Asked later about the experience, Kourtney said giving birth to her son was "surprisingly easy."

"I always thought your first is supposed to be really hard, but it was easy," she told Life & Style. "I have an amazing doctor. He actually delivered me! The room environment was just so relaxing, and everyone I wanted to be there was there—Scott, my mom, Kim and Khloe. No one under 18 is allowed in, so my little sisters Kendall and Kylie couldn't come in. Actually, you're only allowed to have two people in the room because of the swine flu—so we snuck Kim and Khloe in!"

The swine flu shout-out may be a blast from the past, but as many sisters as possible crowding into the delivery room is the way it has been for this family every since. Kourtney was right by Khloe Kardashian's side, too, when her younger sis welcomed daughter True Thompson in April 2018.

Penelope Disick's Cutest Pics

Asked if she was already thinking about having another baby, Kourtney said not yet, but she felt that the 18-month age difference between her and next-youngest sister Kim Kardashian might be a model to go by.

In the meantime, she immersed herself in being a mother of one, making her own baby food, getting rid of her microwave (she read about toxins and decided she'd rather be over-cautious than sorry), taking long walks with Mason in lieu of sprinting back to the gym to get in shape ("carrying him around is like carrying 20 pounds all day," she told Parenting in 2011), letting him sleep in her bed (she became a proponent of attachment parenting and "co-sleeping just kind of happened naturally," she told Redbook) and basically adjusting her schedule to suit her son's.

"I don't want to judge, but I've also met women who think it's cool to be out or away from their baby, and I don't get that, either," Kourtney told Parenting. "When I am out or away, that's when I most want to be with Mason. I do have help when I'm working. It's important to have one person I trust, so I know Mason is taken care of. But every time I am not working, he is with me. Even on an airplane, he is with me even if the nanny is also on the plane."


As for date nights with Scott, "we would be just as happy having a slice of pizza sitting in bed with our son," she shared.

Kourtney also breastfed Mason for 14 months.

"I'm sure all the family thinks I'm [she mimed "a little crazy"] for having them in the bed and breastfeeding for a long time, but whatever," she told Redbook in 2014. Khloe has made fun of Kourtney's hyper-vigilance, such as her various concerns about plastic toys (she's an advocate for wooden blocks, etc.), but Kourtney shrugs off any and all teasing. 

At the same time, despite her unrivaled devotion to her kids—first Mason, and then the same went for Penelope and Reign—there are certain things that might stress out other moms, but that she never freaked out over.

Such as when Kris was on her about getting Mason's nursery all set up by the time he arrived: "I was like, 'People used to have babies in caves; it's going to be okay,'" Kourtney recalled her reply.

There may be no bigger child-size wardrobes than the ones in the homes of assorted Kardashian parents, but Kourtney also cherishes certain hand-me-downs, and few things were more precious than Penelope wearing a pair of her brother's pajamas.

Kourtney considered but ultimately nixed the idea of a water birth at home when she was pregnant with baby no. 2, and Penelope ended up being born at the hospital, like her brother. Her mom did, however, help pluck her out when she was halfway into the world, just as was the case with Penelope's big brother. 

"Kourtney just loves to pull out her own children," Khloe reflected afterward.


Mason insisted that his sister's name was "Sister" at first, but he eventually got the hang of the new girl in town.

Penelope is closest in age, however, to cousin North West, who was born 11 months later, and Kourtney and Kim have collaborated on several joint birthday bashes for their daughters, including a Moana-themed affair in 2017, a sparkly unicorn bash awash in rainbows, with real horses humanely tricked out to look like the mythical creatures, in 2018, and this year's Candyland-in-Calabasas extravaganza.

Kourtney Kardashian and Scott Disick's Co-Parenting Moments

Kourtney has legendarily been set in her ways, once she's decided on a particular way, and that extends to her preternatural comfort in her own skin. Though some of her day-to-day fashion tends toward the modest, she's never shied away from posting a full-on hot-mom bikini pic or otherwise flaunt the figure she acknowledges working very hard on.

That level of confidence was on full display when she posed nude for Dujour when she was pregnant with Reign in 2014.

"To me, nudity is not something to be ashamed of. I'm not embarrassed of my body. I'm at my best when I'm pregnant," Kourtney explained to the magazine. "It's such an amazing feeling, the transformation that your body goes through. There's something about that that's so empowering and beautiful and I just really embrace it."

So, body positivity, check.


A different, very relatable challenge came the following year, however, when Kourtney and Scott broke up after almost a decade together, some of which brimmed with exhausting drama and very similar-sounding arguments about Scott's behavior. But they had always managed to power through the bad times and, incidentally, have three kids together.

So, from then on, after it became clearer in the ensuing months that they were going to stay broken up, it was all about putting on a united front for Mason, Penelope and Reign's sake, and managing their emotions in a productive way. They continued to go on vacation together, Scott remained around for sprawling Kardashian-Jenner holidays, he stayed besties with Khloe and Kris—almost to a confusing extent for the casual observer. But ultimately, that just meant they were making it work—and perhaps only they knew for sure what "it" actually was.

When they were still smoothing out the kinks, though, one of the more unforgettable moments between them was Kourtney having to lay down the law regarding boundaries, since Scott had just been showing up at the house where he no longer lived and treating it as if he still lived there.

"I feel like, if you just wander into my bedroom and go, 'Hey, can I see all your sunglasses?!'..." Kourtney gave an example.


In that particular instance, Scott pushed back, saying he'd been looking for his sunglasses amid all of her sunglasses... but so it went, a lot, as they figured out their new normal.

"I get it," Scott eventually relented. "All things that are understandable in this co-parenting life."

This year, Kourtney had planned to take just the kids on a spring break trip to Finland, but ended up inviting Scott and his girlfriend of two years, Sofia Richie. "They don't make me feel like I'm left out though, which is nice," she explained her decision to Khloe. "Or else I wouldn't go, or invite [Sofia] to come."

Kourtney has become somewhat of an expert in standing up for herself (as have all of her siblings), due to the unsolicited criticism that still pours in from the Instaverse in addition to the thousands of "aws" and "too cutes!" that any photos of her children attract. Mainly her family photos and assorted captions are a mix of funny ("I love a good massage," she quipped recently on a pic of Penelope and Reign rubbing her feet while they were on vacation in Costa Rica), nostalgic and truly heartfelt, know, people love to judge.


For instance, a few (or more) have offered their two cents over the years about Reign's long hair.

"She really need to cut his hair," tweeted one observer in October, to which Kourtney replied, "She really need to not worry about kids that aren't her own. He is a happy boy."

Kourtney doesn't clap back all the time (there wouldn't be enough hours in the day left for anything else!), but when she does... she nails it.

Mason's hair was pretty long back in the day (his style is all his own now, though, and Kourtney has usually been more of the let-the-kids-wear-what-they-want type), and Penelope didn't have her first haircut until this year, in February, at 6 years old.


Meanwhile, Kourtney knows that this is part of the cost of living life so publicly—and that's a life choice she's been thinking a lot about lately, to the extent that there has been serious chatter about whether or not she wants to continue being a part of Keeping Up With the Kardashians, which wraps up its 17th season tonight on E!

"I just decided to spend more time as a mom and put more of my energy there," she told Entertainment Tonight last month about pulling back a bit from the show, "but I'm not saying goodbye." (At the time she was filming season 18 with everyone else, as usual.)

Regardless of what she decides in the long run, she's got everything she needs at home—home being wherever Mason, Penelope and Reign are.

Mason Officially Joins Instagram

Mason opened his first official Instagram account May 25, 2024.

Ice Cream Social

After joining Instagram, Mason shared three posts, including one containing pics of himself hanging out with his sister Penelope.

Brothers' Selfie

Mason also shared this mirror selfie of himself with little bro Reign.

First Family Pic of 2024

Scott shares a pic of his and Kourtney's three kids, Mason (left), Reign and Penelope on his Instagram Stories in January 2024.

Family Fun Time

Scott and his eldest kids Mason and Penelope appear with aunt Kim Kardashian and her kids NorthSaintChicago and Psalm in December 2023.

Sweet Dreams

What's the point of being a parent if you can't embarrass your kids? Reunited with his kids after Kourtney and Travis Barker's May 22, 2022 Italian nuptials, Scott posted an adorable pic of a sleepy Reign on his Instagram Stories.

The Whole Crew Is Here

Scott, Mason and Penelope are joined by family friends for a night full of fun, as Scott captioned his Insta story pic, "Got my crew with me."

Not So Little Anymore

At 9 years old, Penelope poses for a sweet selfie with Scott, which he captioned, "My little girl is getting so big I can't take it!"

Daddy's Girl

Scott shares another sweet photo with his daughter, this time giving her a loving kiss on the head.

When Life Gives You Lemons

Reign, Mason and Penelope are joined by cousin North at their bracelet-making and lemonade stand. Dad Scott even received a custom "Lord" bracelet from Penelope! "Thanks pooshalini," he joked on Instagram Stories. 

Three's Company

Reign, Penelope and Mason play tag on the beach in a sweet pic shared by Scott on July 18. 

Bday Dad

Scott shares a suntanning pic on his 39th birthday featuring kids Reign and Penelope in their backyard. "Happy bday," Scott captions the Instagram Story in May 2021.

Birthday Girl

Scott wishes Kourt a happy 42nd b-day on Apr. 18, 2021. "Happy birthday to the best mom a child could ask for a some more," he writes with a sweet family photo.

Beach Babes

"Love and happiness," Kourtney wrote during a weekend getaway to Santa Barbara with her kids in August 2020.

Swimming Buddies

"Pool party," Scott writes on this photo of Mason and Reign.

Just Like Mom

"Another day another poosh pose," the father of three quips about his daughter.

Solo Swim

"I got 10 on it," Scott writes alongside this playful snap of Reign

Sweet P

"My little precious," the Flip It Like Disick star writes.

Pool Play

"My loves," Scott declares.

Let It Reign

The eldest Kardashian shares to Instagram this cute snap of son Reign.

Going Viral

Kourtney and Mason have a ton of fun goofing around on TikTok.

Happy Holidays

Reign is rockin' around the Christmas tree(s) in this action shot shared to Instagram in December 2019.

Disneyland Fans

"Not sure who has more fun @disneyland #disneyland #HolidaysBeginHere"


Throwback! "Just two cowgirls loving life! #kuwtk," Khloe captions this selfie from the family's Wyoming trip, which played out on The Kardashians.

Reign Turns 5!

"My silly baby is 5 years old today," Kourtney shares on Saturday, Dec. 14, 2019. "Life has so much more meaning with this wild, sensitive boy who has shown me the world through such different eyes."

Mason Turns 10!

Both of Kourtney and Scott's boys were born on December 14, but it was their eldest who celebrated double digits in 2019. "Happiest tenth birthday to the boy who changed my heart forever. No one is cooler or sweeter than you," his mom writes on Instagram. 

Resting Reign

Reign rests on Kourtney after a busy day planting trees.

Sweet Siblings

Penelope and Reign have a sweet sibling moment while at TreePeople in Los Angeles.

TreePeople Tots

"We spent our morning planting trees with @treepeople_org," Kourtney shares on Instagram. "Thank you @futureearth for including us in such a beautiful morning taking care of our Earth."

Little Ones

Scott couldn't love his daughter and his dog more. "My little ones," he writes.

View More Photos From Kourtney Kardashian and Ex Scott Disick's Kids Mason, Penelope and Reign Over the Years