She shared the biggest lie she has ever told (insisting to her parents time and again that she was going to her bestie's house when she was actually visiting a boyfriend). Kendall Jenner also talked about the superpower she most desires (teleportation, or, perhaps time travel). And she almost spilled on her favorite sibling, insisting that, actually, she doesn't have one.
But it was something that Kendall said mid-dare during her and Kourtney Kardashian's 2021 rendition of the classic slumber party game that proved to be the most enlightening.
While filming a round of Truth or Dare for a virtual wellness event put on by Kourt's lifestyle website Poosh, Kendall pulled a card that instructed her to text the family group chat and tell them she had just gotten engaged.
"I just feel like it's weird I'm putting a wedding ring on," she admitted while accepting a sparkler from an off-camera crew member to use as a prop. "But it's believable, so I will do it."
In other words, for those who haven't been keeping up with the second youngest Kar-Jenner's love life, things are serious with her boyfriend of two-plus years, Devin Booker.
In fact, this is the most open Kendall has been about a relationship pretty much ever, the model preferring to keep her romantic entanglements private after witnessing what can happen when they're shared with some 4 million viewers.
"No offense to my older sisters at all, but i think that Kylie [Jenner] and I specifically have had the opportunity to watch our older sisters go through marriages and relationships and break-ups and do them pretty publicly," Kendall explained on the Keeping Up With the Kardashians reunion in June 2021. "It was personal preference from a really young age. I think it makes my life a lot easier and our relationship a lot better, to be honest...I just feel like it's a private matter and not for anybody else to judge or know."
Her rule, executive producer Farnaz Farjam shared on Bravo TV's The Daily Dish podcast that same month, was "she felt like she had to be with someone for at least a year before she lets them be a part of the show and in the show. Because she doesn't always know what people's intentions are."
But now that Kendall and NBA standout Devin have sailed past that particular milestone, well...game on.
By that, we mean, she will happily accept a courtside kiss from the Phoenix Suns shooting guard after cheering him on to a victory over her hometown Lakers. "Devin made a beeline for Kendall after the final buzzer," an onlooker said of the very public display of affection at Los Angeles' Staples Center last October. "Kendall had a huge smile on her face!"
Basically, as one insider put it to E! News, "they are crazy about each other."
After years of guarding her heart, so careful not to make a public misstep, "She feels very secure and confident in their relationship," the insider shared of Kendall, celebrating her 27th birthday Nov. 3, four days after wishing a happy 26th to Devin. "She didn't expect this, but it's become the healthiest and best relationship she has ever been in. She definitely feels like this is different and more serious."
And, yes, it's hard not to notice that the 5-foot-10 818 Tequila founder has a bit of a predilection for skilled ball-handlers, having gone one-on-one with NBA players like Ben Simmons, Blake Griffin and Jordan Clarkson in the past.
"I'm not ashamed that I have a type," she shared on the Keeping Up reunion special, while insisting she doesn't only date ballers, "and I'm also a genuine basketball fan."
Which is why fans were quick to note her game play when she was first spied with the University of Kentucky alum back in April 2020. When one joked she was "passing" NBA players around, she shot back a NSFW reply: "they act like i'm not in full control of where i throw this cooch."
Well, then...
Chemistry aside, in Devin the runway fixture has found a formidable teammate—someone who could hang with her family (he joined his new girlfriend and little sis Kylie for dinner at Nobu in Malibu just months into their courtship) and her friends, the couple enjoying a Jamaican getaway with Justin and Hailey Bieber in September 2021.
He's also proven to be supportive—tagging along for portions of her "Kenny's Tequila Truck" tour last summer—and just as invested in keeping his personal life under wraps.
"Devin is quiet and not interested in being in the spotlight or a celebrity," a source explained to E! News. "She really appreciates that about him and is attracted to that. They are really similar and love just being low-key and staying in and laughing together."
Their commonalities also include a shared love of family, Devin charming her 4-year-old niece Stormi in particular ("Him and Stormi have an amazing relationship. She has the biggest crush on him, and I'm jealous sometimes," Kendall admitted during a September 2021 appearance on The Tonight Show) and an intense competitive spirit.
Having played basketball in middle school, Kendall thought she had enough skills to go toe-to-toe with the two-time NBA All-Star in a round of pool hoops. "He just took it way too seriously—as did I, by the way," she recalled to host Jimmy Fallon. "I had the ball, and he was guarding me, and it was a whole thing. He actually ended up cutting my hand open a little bit with his nail because he took it a little too seriously."
Which is what happens when you challenge someone at the top of their game.
A first-round lottery pick in the 2015 draft, the Michigan native was selected to join the United States men's Olympic basketball team at the 2020 Tokyo Games, bringing home a gold medal just weeks after his Suns missed out on an NBA championship in July 2021.
And getting to wear your boyfriend's shiny new hardware while boating through Lake Tahoe isn't a bad perk. But as Kendall herself said, it's believable she'll be sporting a different type of accessory at some point.
"This is the happiest Kendall has been in a relationship," the source told E! News in April 2021. "It's getting more and more serious."
Having withstood a brief split this past summer, "They worked out their issues," a Kendall insider told E! News, "and decided they want to move forward and be together."
For now, that means trips to the Hamptons, Hawaii and their spot in Idaho. But should she soon be calling her squad to shares news of a real engagement, they'll be just as stoked as they were during that 2021 prank, an "excited" Khloe Kardashian saying her only issue was that the ring "was a little big on your finger."
Because "they love seeing Kendall so happy with someone who brings out the best in her," a source says of her crew's eagerness to bring the athlete into the fold. "Her family loves him and knows how good they are for one another. They love having Devin around and have welcomed him with open arms."
(Originally published Nov. 3, 2021, at 3 a.m. PT)