Kendall Jenner Flirts Back with Devin Booker After Savage Roast

Kendall Jenner has reignited rumors about her romantic life after engaging in a suggestive and playful Instagram interaction with her ex-boyfriend Devin Booker. This exchange occurred shortly after Jenner appeared to tease her former NBA partners in a Super Bowl commercial.

The 30-year-old model responded directly to a comment from the Phoenix Suns star under an Instagram post by Comments By Celebs, which highlighted a clip from Jenner’s recent appearance on The Tonight Show Starring Jimmy Fallon. Booker, who is 29, teased Jenner by writing,

“I bet a million the Seahawks get that ring before you do,”

tagging her in the message.

The Instagram Banter Between Jenner and Booker

Jenner wasted no time responding with a pointed comeback, asking, “how’s the ankle?”—a remark that immediately sparked excitement among fans. Booker quickly replied with a cheeky message, “come rub it,” igniting further speculation about the continued chemistry between the former couple. Followers flooded the comment section, debating whether this playful interaction indicated lingering feelings between them.

This social media flirtation followed Jenner’s recent Super Bowl commercial, which playfully took aim at her professional athlete exes.

Background on Jenner’s Relationships with Professional Athletes

Although the advertisement did not mention any names, it was clear to viewers that it referenced Jenner’s history of dating NBA players, including Booker, with whom she maintained an on-and-off relationship from 2020 to 2022. They were last seen linked together in 2023 before quietly parting ways once more. Neither Jenner nor Booker has commented publicly on their Instagram exchange.

Devin Booker
Image of: Devin Booker

Kendall Jenner’s Appearance on The Tonight Show and Super Bowl Bet

Earlier in the same week, Jenner appeared on The Tonight Show Starring Jimmy Fallon, where she sought advice on her Super Bowl bet. Not knowing much about football, she FaceTimed seven-time Super Bowl champion Tom Brady live on the show to ask whether she should bet on the Seattle Seahawks or the New England Patriots. Jenner joked,

“Sorry to do this to you,”

as she showed Brady seated in his car. Brady shared his detailed pick, only for Jenner to cut him off, drawing laughter from the audience.

Highlights from Jenner’s Self-Deprecating Super Bowl Commercial

Jenner’s Super Bowl commercial for Fanatics Sportsbook gained attention for leaning into the narrative about her relationships with NBA athletes. The ad featured Jenner humorously admitting,

“any basketball player who dates me kind of hits a rough patch,”

while tossing a match into a basket filled with basketball jerseys.

The commercial showcased Jenner walking through a luxurious mansion adorned with portraits of herself and her former boyfriends, their faces conspicuously torn out. She remarked,

“While the world has been talking about it, I’ve been betting on it.”

At one point, she slipped into a black, high-cut one-piece swimsuit and pondered,

“This pool? Basketball boyfriend one missed the playoffs… I guess nobody was getting a ring in this house.”

Continuing her tongue-in-cheek tour of extravagance, she rode in a sleek sports car and boarded a private jet, each tied to the downfall of a different ex. Jenner quipped,

“Boyfriend number two flopped right out of the league,”

and from onboard the jet, she added,

“This cute jet? Thanks boyfriend three!”

As the plane headed to San Francisco for the Super Bowl on February 8, Jenner toasted with a glass of champagne and joked,

“The Kardashian curse, it’s not even my last name.”

This marked her first ever Super Bowl commercial, set to air during halftime.

Jenner’s Past and Present Athletic Relationships

Kendall Jenner has previously been romantically linked to several professional athletes, including Blake Griffin, Ben Simmons, Jordan Clarkson, Kyle Kuzma, D’Angelo Russell, Chandler Parsons, and Devin Booker. Recently, rumors have also connected her to Bad Bunny, the artist scheduled to headline the Super Bowl halftime show.

The commercial also referenced an ongoing family joke. During season three of the Kardashian family Hulu reality show, Kim Kardashian playfully roasted Jenner by wearing a Kendall Starting Five T-shirt, featuring photos of multiple NBA players Jenner has dated.

In 2021, Jenner spoke about her choice to keep relationships private, having observed her older sisters’ public experiences with marriages and breakups. She has also emphasized that she does not exclusively date basketball players, although she enjoys the sport and does not hide her “type.”

The Cultural Impact and Next Steps in Jenner and Booker’s Story

The playful online exchanges between Kendall Jenner and Devin Booker have reignited fan interest in their relationship, especially following Jenner’s cheeky ad that seemingly pokes fun at her romantic history with athletes. This interaction adds a new chapter to their complicated on-and-off connection while maintaining public intrigue about their current status.

With neither party commenting publicly, followers remain eager to see if this will lead to renewed romance or continue as lighthearted teasing. Jenner’s Super Bowl appearance and her candid approach to discussing her dating life continue to fuel media and fan discussions, highlighting the intersection of celebrity culture, sports, and personal relationships.

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