Love, Loyalty and Studying Law on the Side: Inside the Kardashian Moms' Thoroughly Modern Approach to Parenting

Kourtney, Kim, Khloe and Kylie now have nine kids among them and are all rewriting the stodgy rules as they go along

By Natalie Finn May 12, 2019 10:00 AMTags
Kendall Jenner, Stormi Webster, North West, Kim Kardashian, Kourtney Kardashian, Kanye West, True Thompson, Reign Disick, Chicago WestInstagram

Kim Kardashian famously—and quite relatably—did not enjoy being pregnant.

"You know, it was really hard for me to get pregnant, so I do feel really blessed that I am pregnant and, at the end of the day, it is a million times worth it," she told E! News in 2015, when son Saint West was still on the way.

That being said, "I hate it," Kim added. "You know, pregnancy is not for me…You know I've heard stories forever about how amazing pregnancy is from my mom and Kourtney and that's just not the case for me, and I'm not going to sit here and lie and act like it's the most blissful experience."

Motherhood, however, she could eat up with a spoon and come back for more.

Kim and Kanye West have welcomed another son, their fourth child together and second born via surrogate, and according to his proud mommy, "he's perfect."

And, Kim added an hour later, "He's also Chicago's twin lol I'm sure he will change a lot but now he looks just like her."

Kim Kardashian's Quotes on Motherhood

After Saint was born, doctors advised against Kim getting pregnant again, but not for a minute did she give up on the idea of having the big family she'd dreamed of having. So, she researched surrogacy and, despite a few setbacks putting their plans on hold for some months, she and Kanye made it happen.

"Kim always wanted four kids and having two boys and two girls feels perfect," a source told us in January, when they made their plans for baby No. 4 known, just weeks of a year after their third child, Chicago West, was born. "They were very happy with the entire experience the first time and are so grateful to have one more baby."

In turn, this Mother's Day is going to be the most action-packed ever for their sprawling family.

People talk all the time these days about modern families, and few are rewriting the stodgy rules as they go along as much as Kim and her sisters—who have also seen mom Kris Jenner get divorced twice and still manage to steer the ship back into smooth waters. And that ship keeps taking on passengers! Kim, Khloe Kardashian, Kourtney Kardashian and Kylie Jenner now have nine kids between them, they're busier than ever and they've never been happier.


Kylie, who had daughter Stormi Webster in February 2018 and banked her first billion dollars not long afterward, has said that her life irrevocably changed for the better after becoming a mom. Her pregnancy at 19 may have shocked the world, but she didn't bother taking the temperature of the zeitgeist when deciding how to proceed.

What Kylie did do is not share the particulars of her journey with her 134 million Instagram followers until it was over—only then could the narrative fully belong to her. 

And while life is as riddled with selfies and social media as ever these days, "the way that I look at things is a lot more positive," the now 21-year-old Kylie Cosmetics mogul told Interview Germany. "I really feel like my life didn't start until I had [my daughter]."

Stormi Webster's Cutest Photos

Kourtney said something similar in 2012, when she was pregnant with baby No. 2, telling Parents that being a mom is "definitely my favorite role in life. It has changed me and made me realize there is nothing else I would rather do with my time. Being a mom is what life is about. I hope people realize what the priorities in life should be and know not everything has to be perfect."

As in, a reminder to those wondering at the time if she and Scott Disick were going to get married: Mind your own business.


Kylie envisions giving Stormi a sibling one day, but she's not in any rush—nor are she and Stormy's dad, Travis Scott, in any rush to change the status of their relationship while being partners in everything—including love, parenting and home-ownership—is working out so well for them. (Not to mention, Kylie's got a skincare line on the way first.)

This past January, a source told E! News that Khloe and Kylie loved being pregnant together in 2017 and early 2018, during much of which Kim's surrogate was also expecting Kimye's third child, meaning some epic baby-planning was underway all at once. The sisters even joked about doing it all over again so they'd have yet another round of close-in-age cousins, True, Stormy and Chicago often affectionately being referred to as the "triplets."

That was, incidentally, before all hell broke loose.

True Thompson's Cutest Photos

Khloe, who also let nothing stand in her way when she felt it was the right time for her to start her own family, had to adjust her aspirations when it came to having more kids with now ex-boyfriend Tristan Thompson. Determined to make it work for True's sake last year, she finally broke it off with the basketball player a few months ago after friends told her he had hooked up with Kylie's now former best friend Jordyn Woods.

When a fan expressed hope via Twitter that Khloe would find a guy who deserved her, she replied, "Baby True made it all worth it. Thank you for your beautiful message."

Another silver lining, particularly for the rest of her family, was that Khloe has permanently relocated back to L.A. after spending a lot of the previous year in Cleveland, where Thompson plays for the Cavaliers.

"I definitely feel like we are more connected now, especially that Khloe's back and we're hanging out with all the babies," Kim told E! News last summer when Khloe was home during the NBA off-season. "All the kids want to hang out. It's just a whole different experience now. It's so much fun."

Instagram/Kourtney Kardashian

While Chicago, Stormy and True are especially close in age, the range for the littlest Kard-Jenner generation goes from 3 days old to 9 years old, the big birthday Mason Disick celebrated in December. And with all the sisters living within 25 miles of each other (only the traffic between Beverly Hills and Calabasas makes it feel longer), all the kids have grown up together. 

Kim also told us last July, "I think we're even closer now because Kourtney and I, even if we don't disagree on some parenting tips, we'll discuss them thoroughly and we respect each other's rules, but we pick up the slack for each other too. I know that if Kourtney's out of town, then the kids will sleep at my house and we'll plan these fun things where the kids always feel loved. We're always helping each other out."

Kylie, however, was the one who was up on all the new baby gear, Kim added. 

Kourtney Kardashian and Scott Disick's Family Pics

Kourtney, the first of all of them to start a family, has slowly but surely become the seasoned veteran when it comes to modern mothering. She and Scottbroke up in 2015 and, even when the sight of him made her want to scream (or cry, or even laugh sometimes), Kourtney powered through to make life remain as normal as possible for their three kids, Mason, Penelope and Reign.

"I feel like I can show a message, too, of like parents can get along and work together and travel together," she said on Today in February. "And I think it's a good message to show other people."

Last month, the friendly exes made a YouTube video together in which they both acknowledged it hadn't been easy, but, Scott said, "the fact that we've tried and made it work makes life that much better. I couldn't imagine raising three children with somebody I couldn't speak to every day."

Instagram / Kanye West

"The hardest part was when we both started new relationships," Kourtney added. "That caused fights between you and I about introducing the kids. We literally had to go to therapy to be able to, like, communicate together."

Scott replied, "The biggest challenge was just trying to figure out how we separate our relationship as friends and parents and still be on the same page, and what's, I guess, appropriate and what's not and when to be able to talk to each other. In the beginning, you set good [boundaries] and we learned from that and we've gotten to a good place."

Both are lucky that Kourtney's whole family is supportive of the master plan. Some days have felt more supportive than others, but overall... they're on board.

Khloe, too, has seen firsthand her big sister working hard to figure it out, and she has worked on doing the same with Tristan.

Kim Kardashian's 4th Baby Shower

Even in the earliest, rawest days of their split, she did her best to be civil, tweeting in March, when someone remarked that all True needed was her mom, "Thank you love! You're so very sweet. But he is a good dad to her. My sweet and special baby True will NEVER be put in the middle of him and I. I can promise that."

In April, she and Tristan were both at True's big backyard 1st birthday party, as were Kylie, Kim and Kourtney and a bunch of True's cousins.

And despite the heartbreak, taking care of her daughter has still made life feel better than ever.

"I am so utterly obsessed with her," Khloe told People last month. "This first year has been amazing. And I really feel like I was meant to do this."

Kim Kardashian & Kanye West's Baby No. 4's Lavish Lifestyle

Kim technically has the most traditional set-up of all of them, having been married to Kanye West since 2014, but there are certainly a few things about their lifestyle—jetting all over the world, eldest daughter North West covering Vogue Kids at 21 months old, occasional meetings at the White House, going to the Met Gala three days before becoming parents of four—that aren't particularly normal.

And Kim is only adding more to her plate: she's independently studying to become a lawyer, with an eye on taking the bar exam in 2022, and it was just reported that she was quietly giving money to the 90 Days of Freedom Campaign, which has helped get 17 inmates released from federal prison over the past three months.

Being on Keeping Up With the Kardashians for more than 11 years and being intertwined with her fans via social media for as long, it hasn't always been easy for her to tune out some of the more hurtful noise—but in recent years, since having kids and discovering this passion for legal justice that's been simmering beneath the surface, she just doesn't have time for the drama anymore.

Defying people's expectations is fun, though.


Now, Kim told Vogue recently, "I love to be put in a situation where I can have a conversation with someone who might not be inclined to think much of me, because I can guarantee they will have a different opinion and understand what's important to me after they've met me."

And despite her most unusual of paths—to fame, to love, to the law—she had the most understandable of concerns before deciding to have a family of her own.

"Before I had kids, I remember just thinking like, Wow, [my parents] had it so together. Am I ready?" Kim wrote in an essay last year for Wealthsimple,  But you're never ready. I say that to all my friends. Me in my 30s, Kanye was in his 30s, and I'm like, If we're not ready now... I mean, this is pathetic. So we're going for it. And it just happened — I was so freaked out. I was like, I thought my life was over. I was just so not a parent. I literally thought my life was over."

But it had only just begun.