Kendall Jenner shamelessly flirts with ex Devin Booker online after roasting NBA exes in savage Super Bowl ad

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Kendall Jenner is once again sparking rumors about a possible reconciliation with her former boyfriend, Devin Booker. This comes after a playful back-and-forth on Instagram, shortly after she jokingly referenced her past NBA relationships in her first-ever Super Bowl ad.

People were surprised when the 30-year-old model responded directly to a comment from the Phoenix Suns player on an Instagram post. The post featured a video of Jenner’s recent interview on The Tonight Show Starring Jimmy Fallon.

Devin Booker, 29, playfully challenged Kendall Jenner, betting her a million dollars that the Seahawks would win a championship before she did. He mentioned her in the social media post.

The reality star quickly responded with a pointed question: ‘How’s the ankle?’ This immediately sparked a huge reaction from fans.

Booker playfully responded with a suggestive comment – ‘come rub it’ – which led fans to believe there might still be something between him and his ex-partner.

This lighthearted exchange follows Jenner’s recent Super Bowl ad, which playfully poked fun at her past relationships with athletes.

Although the advertisement didn’t mention anyone specifically, viewers quickly realized it seemed to refer to Kendall Jenner’s past relationships with basketball players, including Devin Booker, with whom she had an intermittent romance from 2020 to 2022.

The pair were last linked in 2023, before quietly going their separate ways once again. 

Neither Jenner nor Booker has publicly addressed the exchange.

This week on The Tonight Show, Kendall Jenner jokingly FaceTimed Tom Brady, the famous football player, to ask him who he thought would win the Super Bowl – the Seattle Seahawks or the New England Patriots. She was trying to decide which team to bet on.

Jenner confessed she wasn’t very knowledgeable about football, and jokingly asked Fallon if she could call someone for help.

Seeking the ultimate edge, the beauty proceeded to FaceTime the football legend live on air.

Jenner playfully apologized while showing the audience a surprised Brady sitting in his car. She looked stunning in a beaded, tiger-striped dress.

Brady started explaining his choice in detail, but Jenner suddenly interrupted him, which made the audience laugh.

Kendall Jenner recently sparked conversation with a humorous Super Bowl commercial for Fanatics Sportsbook. The ad playfully references the frequent media attention on her past relationships with basketball players.

The commercial leaned into the idea of a ‘curse’ surrounding dating Jenner, with her jokingly suggesting that any basketball player she dates faces hard times. She then lit a pile of basketball jerseys on fire, visually representing this ‘rough patch’.

She casually walked through her opulent home, filled with portraits of herself and her ex-lovers—but with the faces of the exes deliberately torn out. With a playful tone, she remarked, ‘Everyone’s been discussing this, and I knew it was going to happen all along.’

As a style expert, I have to say one of the most captivating scenes in the ad featured Kendall Jenner. She made a splash – literally! – walking out to the pool in a sleek, black swimsuit. It was a really minimalist look, but the high-cut design beautifully highlighted her legs as she effortlessly glided into the water. It was all about confidence and understated glamour.

She thought aloud, looking at the pool. ‘So, her basketball-playing boyfriend didn’t make the playoffs… meaning no championship celebrations – and no ring – for anyone here.’

The model playfully showed off her lavish lifestyle, driving a stylish sports car and flying on a private jet. She jokingly blamed each expensive treat on a different ex-boyfriend’s misfortune.

She dismissed her second boyfriend as a complete mismatch, then casually mentioned her current boyfriend while gesturing to the private jet: ‘This adorable plane? A gift from my new boyfriend!’

While watching the game, Jenner announced it was time to try something different – betting on the football players themselves. She then urged viewers to place bets on the Super Bowl using Fanatics Sportsbook.

A flight attendant told Kendall Jenner they were flying to San Francisco for the Super Bowl between the Seahawks and the Patriots on February 8th. Jenner smiled and jokingly said, ‘Football boyfriend.’

Watching the plane lift off, I saw Jenner raise a glass of champagne and deliver this amazing line: ‘The Kardashian curse? It’s not even my last name!’ It was perfect – a really clever way to address everything everyone says about the family.

The commercial, which marks Jenner’s first-ever Super Bowl ad, will air during halftime.

Jenner has dated several professional athletes over the years, including Blake Griffin, Ben Simmons, Jordan Clarkson, Kyle Kuzma, D’Angelo Russell, Chandler Parsons, and most recently, Booker.

Recently, people have connected the model to Bad Bunny, the artist who will be performing at the Super Bowl halftime show.

The commercial includes a playful reference to a running joke within the family. Back in season three of their Hulu reality show, Kim Kardashian jokingly teased Kendall by wearing a shirt that said ‘Kendall Starting Five.’ The shirt featured pictures of several NBA players Kendall had previously dated.

In 2021, Jenner explained that she chooses to keep her romantic life private because she’s seen her older sisters experience very public marriages, relationships, and breakups. This made her want to protect her own personal life.

She’s clarified that she doesn’t exclusively date basketball players, though she does enjoy the sport and openly admits she has a preference for a certain type of person.

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2026-01-29 20:51