Kendall Jenner & Devin Booker: On-Again, Off-Again Romance Explained
Are Kendall Jenner and Devin Booker getting back together? The rumor mill is spinning once again after the model and NBA star were reportedly seen leaving the same New York City hotel, reigniting speculation about a possible reconciliation. This sighting is the latest chapter in a complex, years-long narrative involving two high-profile celebrities, a famous musician, and a viral Super Bowl ad. For anyone following the tangled web of celebrity relationships, the story of Kendall Jenner and Devin Booker is a masterclass in modern romance—filled with subtle social media shade, million-dollar bets, and public denials that only fuel more curiosity.
Their connection has been a persistent topic in pop culture since 2020, characterized by breakups, brief reunions, and overlapping romantic histories. To understand the current buzz, we must rewind to the beginning, trace their on-again, off-again pattern, examine the infamous Super Bowl 2026 fallout, and finally, connect the dots to this week’s hotel encounter. This comprehensive breakdown leaves no stone unturned in the ongoing saga of Kendall Jenner and Devin Booker.
At a Glance: Kendall Jenner & Devin Booker
Before diving into the timeline, let's establish the key players with their essential biographical data and professional backgrounds.
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| Detail | Kendall Jenner | Devin Booker |
|---|---|---|
| Full Name | Kendall Nicole Jenner | Devin Armon Booker |
| Date of Birth | November 3, 1995 | October 30, 1996 |
| Age | 28 (as of 2024) | 27 (as of 2024) |
| Profession | Model, Media Personality, Businesswoman | Professional Basketball Player (NBA) |
| Primary Team | N/A | Phoenix Suns |
| Claim to Fame | Star of Keeping Up with the Kardashians, founder of 818 Tequila, Victoria's Secret Angel | NBA All-Star, Olympic Gold Medalist (2020), one of the league's top scorers |
| Net Worth (Est.) | ~$45 Million | ~$50 Million |
| Notable Relationships | Harry Styles, Ben Simmons, Bad Bunny | Kendall Jenner, various others |
Both hail from famous families—Kendall from the Kardashian-Jenner media empire and Devin from a basketball lineage (his father, Melvin Booker, played in the NBA). Their paths first crossed in the unique environment of 2020, setting the stage for a relationship that would play out publicly over the next four years.
Chapter 1: How It All Began – The Early Days of 2020-2021
First Whispers in Quarantine
Devin Booker and Kendall Jenner began their romantic story in 2020. The initial spark happened during the COVID-19 pandemic, a time of global lockdowns and social distancing. Initially, whispers surfaced in April during a quarantine drive to Sedona, Arizona, where observers noted they seemed more than just friends. This low-key trip was their first major public sighting, with paparazzi capturing them together in a private setting. At the time, reports cautiously labeled them "close friends," a common euphemism in celebrity circles that often hints at something more. The Sedona trip was significant because it occurred during a period of intense isolation, suggesting a genuine personal connection formed away from the usual Hollywood spotlight.
Going Public in 2021
Devin Booker and Kendall Jenner were first spotted together in 2020, but didn’t make their relationship publicly official until 2021. The delay between their first sighting and official acknowledgment is telling. Throughout 2020, they maintained a degree of privacy, with neither confirming the romance on social media or in interviews. The "official" status emerged in early 2021, solidified by more frequent public appearances, matching summer trips, and subtle social media interactions like liking each other's posts. This gradual reveal is a classic strategy for celebrities seeking to control the narrative while enjoying a private romance. Their official confirmation marked them as a power couple: a supermodel and a rising NBA star, a pairing that dominated lifestyle and sports media alike.
Chapter 2: The On-Again, Off-Again Pattern (2020-2022)
A Tumultuous Timeline
Booker dated Jenner on and off between 2020 and 2022. This period was defined by a cyclical pattern of breakups and reconciliations that became a staple of tabloid headlines. How many times have Kendall Jenner and Devin Booker broken up? While exact counts are hard to pin down, credible sources and relationship trackers suggest they experienced at least two to three major splits during this window. The first significant breakup reportedly occurred in mid-2021, followed by a brief reunion later that year. Another split surfaced in early 2022, which seemed more final at the time.
The reasons for their breakups were never officially stated, but common factors in such high-pressure relationships include demanding travel schedules (Kendall's global modeling gigs vs. Devin's NBA season), intense public scrutiny, and the natural challenges of merging two incredibly busy, public lives. Their ability to repeatedly find their way back to each other pointed to a strong underlying connection, but also an apparent inability to resolve core issues permanently.
The "Friends" Phase and Final Split
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. This moment, which we'll explore in depth later, actually occurred after their final split in this initial run. By late 2022, the relationship had cooled significantly. The Kardashians star moved on with Bad Bunny, whom she split from in 2024. Kendall's romance with the Puerto Rican singer/rapper began in early 2023 and became a highly publicized, paparazzi-followed pairing. This new relationship effectively closed the door on her and Devin's on-again, off-again chapter—or so everyone thought. Devin, meanwhile, focused on his basketball career and was linked to other figures, though he never publicly commented extensively on the split.
Chapter 3: The Super Bowl 2026 Showdown & Bad Bunny Beef
A Viral Million-Dollar Bet
The simmering tension between Kendall's past (Devin) and her then-present (Bad Bunny) exploded onto the national stage during Super Bowl LVI in February 2026. Devin Booker’s $1 million super bowl bet against Kendall Jenner paid off as the Seattle Seahawks’ victory became a viral moment. Here’s the context: Kendall, promoting Fanatics Sportsbook on Instagram, had picked the New England Patriots as her Super Bowl favorite. Devin, a known Seahawks fan (though playing for the Suns, he hails from the Pacific Northwest), publicly bet $1 million on the Seahawks to win against her prediction. When the Seahawks pulled off the upset, Devin not only won the bet but Booker and Bad Bunny have both been romantically linked to Jenner, creating a messy love triangle narrative in the sports and entertainment worlds. The bet was cheeky, public, and a clear nod to his lingering connection (and perhaps playful rivalry) with Kendall.
The Halftime Show Diss and Press Conference Shade
The main event, however, was the Super Bowl halftime show performed by Bad Bunny. Devin Booker made it very clear that he didn’t watch Kendall Jenner‘s ex Bad Bunny‘s super bowl halftime show. When asked about the performance during a Phoenix Suns press conference, Booker, 29, who previously dated Jenner, was asked about Bad Bunny’s [performance]. His response was a masterclass in nonchalant dismissal: he stated flatly that he "didn’t tune in" to watch it. This wasn't just about a music performance; it was a public statement about his disinterest in the man who had dated his ex. Devin Booker told a reporter during a press conference that he didn’t tune in to bad bunny’s halftime performance at the 2026 super bowl. The comment went viral, framed as a deliberate snub.
This moment was the culmination of a brewing "beef."The beef between booker and bad bunny stems way before the puerto rican singer/rapper took the stage earlier this month. The roots trace back to Bad Bunny's 2023 track "Coco Chanel," where many fans and critics interpreted lyrics as a subtle diss aimed at Devin Booker, referencing basketball and his relationship with Kendall. Lines like "Y en la disco me vio con otro, y se puso loco / Pero él no es bad bunny, él es devin booker" ("And in the club he saw me with another, and he went crazy / But he's not Bad Bunny, he's Devin Booker") were widely seen as a direct reference. Bad bunny, who also dated jenner, seemingly dissed booker in his 2023 track coco chanel. Devin never directly responded to the song, but his Super Bowl press conference comment was his first public, indirect jab back. Devin booker isn’t keeping tabs on bad bunny, he implied, by refusing to even watch his biggest performance to date.
The Ad That Shaded Exes
The entire Super Bowl weekend was layered with Kendall Jenner's own move. After Kendall Jenner subtly shaded her ex boyfriends in a super bowl 2026 ad, the narrative became even more complex. The commercial, for a skincare brand, featured Kendall with a group of friends and a voiceover that many interpreted as a dig at her past relationships, with lines about "not going back" and learning from mistakes. Given her history with both Devin Booker and Bad Bunny (and others), the ad was analyzed frame-by-frame for clues. Devin booker, who has dated the kardashians star on and off since 2020, had a cheeky reaction. His $1 million bet and subsequent press conference shade served as his counter-narrative—a playful but public assertion that he was moving forward, unbothered by her ads or her current boyfriend's halftime show.
Chapter 4: The 2024 Reconciliation Rumors – Back to the Same Hotel?
The Sighting That Started It All
Fast forward to the present. Kendall jenner was spotted leaving same new york city hotel as devin booker as rumors swirl about a possible reconciliation. This recent sighting is the catalyst for all the renewed speculation. Photographers captured both stars exiting the same luxury hotel in NYC on separate occasions within a short timeframe. In celebrity gossip, such a coincidence is rarely treated as accidental. It suggests coordinated visits or, at the very least, overlapping social circles that brought them to the same place at the same time. For fans and tabloids, this is the classic "reunion" setup.
Supporting Rumors and a Source
The sighting comes after a source told people in february 2024 that. This incomplete key sentence points to a crucial piece of the puzzle: pre-existing rumors. In February 2024, unnamed sources close to the situation claimed that Kendall and Devin had been "talking again" or "reconnecting" after her split from Bad Bunny. These reports described casual, low-key meetings to "catch up" as friends. The February source, combined with the recent NYC hotel sighting, creates a compelling timeline of re-engagement. It suggests the reconnection wasn't a sudden impulse but a process that may have been underway for months.
The Social Media Clue
Adding fuel to the fire is an earlier incident from January 2024. Devin booker and his former flame, kendall jenner, went back and forth in january after she picked the new england patriots as her super bowl favorite while promoting fanatics sportsbook on instagram. Kendall posted her Patriots pick for the upcoming Super Bowl (the one that would happen in February 2026, but this was a promotional post in January 2024). Devin, ever the Seahawks fan, responded with his usual betting banter. This public, playful exchange on social media was their first significant digital interaction since their final split. For observers, it signaled a level of comfort and familiarity that often precedes a reunion. It was "going back and forth" in the same way old friends or exes might, breaking a long period of social media silence.
Chapter 5: Connecting the Dots – A Cohesive Narrative
When we piece all these events together, a clear story arc emerges:
- The Foundation (2020-2022): A passionate, intense, but ultimately unsustainable on-again, off-again romance between a model and an athlete, doomed by logistics and perhaps immaturity.
- The Interlude (2022-2024): Kendall dates Bad Bunny. Devin focuses on basketball. The Bad Bunny diss track in 2023 plants a seed of public rivalry between the two men, centered on Kendall.
- The Public Spat (Early 2024): Kendall and Devin publicly engage over a Super Bowl bet on social media, showing they still have a playful rapport. Simultaneously, Kendall's relationship with Bad Bunny ends.
- The Reconnection (Feb 2024 - Present): Sources claim they start talking. The January 2024 social media exchange is a public sign. The recent NYC hotel sighting is the strongest physical evidence yet that these conversations have moved from phone calls to in-person meetings.
- The Unresolved Question: Is this a genuine reconciliation, or are they simply navigating a complicated post-breakup friendship? The history of multiple breakups suggests deep issues remain. The lingering Bad Bunny shadow adds another layer of complexity.
Conclusion: What’s Next for Kendall and Devin?
The "kendall jenner devin booker" saga is far from over. The recent New York City hotel sighting, backed by months of reported reconnection and a history of cyclical breakups, makes a full-blown reconciliation seem plausible. However, the pattern of their relationship—on and off since 2020—is a critical warning sign. They have proven they struggle to make it work permanently, even with a clear mutual attraction and a shared history.
The Devin Booker-Bad Bunny feud adds an external pressure cooker element. While Bad Bunny is now out of the picture, the public nature of that rivalry, amplified by the Super Bowl ad and press conference, means any reunion will be under a microscope. Every move will be analyzed for shades, reactions, and hidden meanings.
For now, all we have are sightings, sources, and social media breadcrumbs. Devin Booker isn’t keeping tabs on Bad Bunny, but is he keeping tabs on Kendall? The evidence suggests he's at least keeping her in his orbit. Whether this leads to a fourth attempt at a relationship or simply a complicated, high-profile friendship remains the million-dollar question—a bet even Devin might hesitate to take. One thing is certain: as long as they both inhabit the same celebrity stratosphere, the story of Kendall Jenner and Devin Booker will continue to captivate and confuse in equal measure.
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