Devin Booker and Kendall Jenner may have gone their separate ways, but a recent social media exchange suggests the connection has not fully faded.
The interaction began during a Super Bowl betting promotion and quickly turned playful. Fans watched as a lighthearted moment escalated into a flirty exchange that mixed sports rivalry with personal history.
The comments appeared under an Instagram post shared by Michael Rubin. Rubin had posted a clip from Jenner’s appearance on The Tonight Show Starring Jimmy Fallon.
In the segment, Jenner joked about sports betting and even FaceTimed Tom Brady while discussing her Super Bowl pick. The relaxed tone set the stage for Booker to join the conversation.
The Phoenix Suns star said he would “bet a million” that the Seattle Seahawks would win a championship ring before Jenner ever did. He tagged his former partner directly.
After Kendall Jenner subtly shaded her ex boyfriends in a Super Bowl 2026 ad, Devin Booker, who has dated The Kardashians star on and off since 2020, had a cheeky reaction. https://t.co/ghQtPqkvbs pic.twitter.com/YIijJYHitv
— E! News (@enews) January 29, 2026Jenner responded with an eye-roll emoji and a sharp remark about Booker’s recent ankle injury. She asked how he was holding up.
Booker then escalated the exchange by replying, “come rub it.” The comment instantly caught the attention of fans and sent them into a frenzy.
The playful tone carried extra meaning due to their shared past. Booker and Jenner dated on and off between 2020 and 2022. They largely kept the relationship private but frequently made headlines.
Both are currently single. Their easy banter suggested familiarity rather than tension, which fans quickly picked up on.
The timing added to the entertainment value. Booker recently suffered an ankle sprain during a loss to the Atlanta Hawks and is expected to miss about a week. The injury has kept him sidelined, but he remains active on social media.
Devin Booker to Kendall Jenner over her Patriots Big Game prediction with @fanaticsbook:
“I bet a million the Seahawks get a ring before you do 🫣”
💀💀💀 #BetOnKendall pic.twitter.com/t5goXNP89U
— Legion Hoops (@LegionHoops) January 29, 2026Jenner, meanwhile, has promoted Fanatics Sportsbook ahead of the Super Bowl. She leaned into jokes about the so-called “Kardashian Curse,” a superstition linked to athletes she has dated.
That theme appeared in her recent commercial, which playfully references past relationships. Soon after, Booker posted a photo of himself in a classic SS Chevy, which fans interpreted as a subtle nod to Jenner’s campaign visuals.
Read: Kendall Jenner Mocks ‘Kardashian Curse’ in Super Bowl Ad
Booker, who has won Olympic gold medals with Team USA, struck a chord with his championship ring joke. Jenner embraced the underdog role by picking the New England Patriots to win Super Bowl LX.
Whether the exchange was pure humour or hinted at lingering chemistry, fans were quick to enjoy the moment.
