Kendall Jenner has long been Hollywood's enigmatic dater. Her high-profile romances weave through musicians, models, and NBA stars with tantalizing on-again, off-again drama. From Harry Styles' stolen road-trip kisses to Bad Bunny's Coachella sparks and Devin Booker’s courtside chemistry, her love life fuels endless tabloid fire.

Yet, amid the whirlwind, her iconic pairing with Phoenix Suns ace Devin Booker stands tallest, with two years of steamy Phoenix getaways, yacht escapes, and Super Bowl sidelines that screamed soulmate synergy.

Just when fans buried that flame, Jenner's savage Super Bowl ad roasting her hoops exes collided with Booker's flirty Instagram retorts.

Kendall Jenner and her ex-boyfriend Devin Booker sparked romance rumors with flirty Instagram exchanges after her Super Bowl 2026 ad debut.

The Phoenix Suns star playfully commented on a Fanatics Sportsbook post, betting "a million the Seahawks get that ring before you do" with a blushing emoji, responding to her Patriots pick.

Jenner fired back with an eye-roll emoji asking "How's the ankle?", referencing his recent sprain.

This prompted Booker's steamy reply: "Come rub it."

The banter erupted from Jenner's Bet on Kendall commercial, her first Big Game spot, where she leaned into the infamous "Kardashian Curse" myth tying her NBA romances to players' slumps.

She quipped, "Any basketball player who dates me kind of hits a rough patch... I've been betting on it." The ad peaked with her moving on from basketball to place a $1 million bet on the New England Patriots to beat the Seattle Seahawks, a move that immediately drew a 'million-dollar' challenge from Devin Booker on Instagram.

The pair, who dated on-and-off from 2020 to 2022, last linked in early 2025, made the viral exchange a cheeky nod to their history. This playful shade-throwing highlights Jenner's history with NBA stars like Blake Griffin and Ben Simmons, fueling fan speculation about a rekindled spark amid Booker's injury recovery.

Simone Ashley and Kendall Jenner Stir Up Fashionable Chaos for 'The Devil Wears Prada 2'

While the playful banter heats up online, another incident narrated by her sister is making rounds of the internet.

Kylie Jenner has opened up about a painful childhood mishap during a game of hide-and-seek with her sister Kendall, which left her with a lasting leg scar. While hiding inside an enclosed space during playtime at their family home, Kylie badly injured her leg, requiring medical attention, resulting in a visible mark she later displayed confidently at events like the Golden Globes afterparty.

In interviews and on their reality shows, Kylie has reflected on the incident with humor, noting how it became part of their wild sibling adventures amid the Kardashian-Jenner chaos. Kendall has echoed these stories, recalling their rocky yet loving dynamic filled with mischief, tears, and unbreakable bonds that shaped their closeness today.

This sisterly history of scrapes and support mirrors Kendall's own playful jabs at exes like Devin Booker, showing how Jenner siblings turn personal lows into public triumphs, proving family ties endure even as romances flicker back to life.

Is Kendall Jenner Single? Who Is the Super Model Dating Right Now?

What do you think about Kendall Jenner shading her NBA past? Let us know in the comments