Kendall Jenner and Devin Booker Turn Flirty Following Her New Ad Campaign

Kendall Jenner and Devin Booker sparked fresh buzz after a flirty Instagram exchange tied to her viral Fanatics Sportsbook ad, reviving fan speculation about their on-and-off dynamic following multiple public sightings over the past two years.

Kendall Jenner and Devin Booker are once again fueling pop culture speculation, this time with a playful exchange on Instagram that quickly caught fans’ attention.

The former couple traded flirty comments beneath Jenner’s latest Fanatics Sportsbook advertisement, reopening conversations about their complicated history and whether the door is fully closed on their relationship.

The interaction followed the release of Jenner’s viral campaign, which humorously acknowledges her dating history with professional basketball players, including Booker. While neither has confirmed anything romantic, the timing and tone of their exchange reignited curiosity surrounding a relationship that has quietly lingered in the public eye.

Kendall Jenner Leans Into the Narrative

Jenner’s Fanatics Sportsbook ad, titled "Bet on Kendall," embraces a long-running internet joke that suggests NBA players who date her experience a decline in performance. Instead of pushing back, Jenner uses self-aware humor to flip the narrative.

“While the world’s been talking about it, I’ve been betting on it. How else do you think I can afford all this… modeling!?” she says with a laugh in the ad.

The commercial ends with Jenner boarding a private jet en route to San Francisco ahead of the 2026 Super Bowl. “But today, it’s time to bet on something new. Football players,” she adds, punctuating the joke while expanding the conversation beyond basketball.

The ad quickly went viral, drawing praise for its wit and Jenner’s willingness to poke fun at herself. It also drew the attention of someone very familiar with the narrative.

Devin Booker’s Flirty Response

Booker chimed in directly on Instagram, posting a comment that fans immediately clocked as playful. “I bet a million the Seahawks get that ring before you do @kendalljenner 🤗,” he wrote.

Jenner responded just as quickly. “@dbook 🙄 how’s the ankle?” she replied, referencing Booker’s recent injury.

The Phoenix Suns star had the final word. “@kendalljenner come rub it,” Booker responded, turning the exchange into a moment that spread rapidly across social media.

Booker suffered a right ankle sprain during a game against the Atlanta Hawks on Friday, January 30, 2026. While unrelated to the ad itself, the injury added another layer of context that fans were quick to connect.

A Relationship That Never Fully Faded

Jenner and Booker were first linked in April 2020 and made their relationship Instagram official in February 2021. Known for keeping their romance private, the pair largely avoided public commentary while maintaining a steady presence together.

They briefly split after their second anniversary in June 2022, reconciled soon after, and officially parted ways in October 2022. Despite the breakup, sightings over the following years suggested their connection may not have fully ended.

In February 2024, Jenner and Booker were spotted together at the 2024 Super Bowl in Las Vegas. Booker attended the event alongside Jenner, members of the Kardashian family, Justin and Hailey Bieber, and Ciara and Russell Wilson.

By September 2024, the two were seen having dinner together in Miami, further fueling speculation that they had reconnected. In February 2025, they were once again spotted together, this time in Aspen, Colorado, a favorite getaway for both.

Their last public sighting came in September 2025, when Jenner and Booker were seen leaving the same hotel in New York City. Since then, fans have not seen them together, making the recent Instagram exchange their most notable interaction in months.

Kendall Jenner’s High-Profile Dating History

Jenner’s ad also subtly references her broader dating history, which has included NBA players Jordan Clarkson, Blake Griffin, and Ben Simmons. Over time, those relationships have become part of online lore, often discussed alongside jokes about superstition and sports performance.

Whether the Instagram exchange was harmless flirting or something more, Jenner and Booker once again proved their ability to capture attention without saying much at all. With years of overlapping timelines, public sightings, and now a viral ad moment, the curiosity surrounding their relationship shows no signs of fading anytime soon.