The Ultimate Timeline: 7 Reasons Why Devin Booker And Kendall Jenner’s On-Again, Off-Again Romance Is Back On

The whirlwind romance between supermodel Kendall Jenner and NBA star Devin Booker is once again the hottest topic in celebrity news, with fresh sightings suggesting the famously private couple is back on. After a significant split in late 2022, and Jenner’s high-profile relationship with musician Bad Bunny, recent reports from late 2024 and early 2025 have confirmed that the Phoenix Suns shooting guard and the reality TV star are "slowly rekindling" their deep connection, sparking a frenzy among fans who have followed their on-again, off-again saga for years. This article dives into the complete history of their relationship, the latest updates as of today, December 10, 2025, and the key reasons why this power couple keeps finding their way back to each other.

The latest news comes after the pair were spotted exiting the same New York City hotel, fueling rumors that their reunion is far more than a casual friendship. Their history is complicated, marked by long periods of intense dating, supportive public appearances, and abrupt breakups attributed to conflicting schedules and demanding careers. Despite the challenges, the bond between the founder of 818 Tequila and the Olympic gold medalist appears to be one that neither can fully walk away from.

The Comprehensive Profile: Devin Booker and Kendall Jenner Biography

To understand the dynamics of this high-profile couple, it is essential to look at the impressive individual careers that define them.

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Kendall Nicole Jenner

• Born: November 3, 1995 (Age: 30)
• Birthplace: Los Angeles, California, U.S.
• Parents: Kris Jenner and Caitlyn Jenner (formerly Bruce Jenner)
• Occupation: Supermodel, Media Personality, Businesswoman, Socialite
• Career Highlights: Rose to fame on the reality television show *Keeping Up with the Kardashians* (KUWTK). She has walked the runway for major fashion houses like Chanel, Marc Jacobs, and Fendi. In 2017, she was named the world’s highest-paid model by Forbes. She is the founder of the premium spirit brand, 818 Tequila, which launched in 2021.
• Key Entities: Kardashian-Jenner family, Kylie Jenner, Kris Jenner, Gigi Hadid, Met Gala, Victoria's Secret, 818 Tequila.

Devin Armani Booker

• Born: October 30, 1996 (Age: 29)
• Birthplace: Grand Rapids, Michigan, U.S.
• Parents: Veronica Gutierrez and Melvin Booker (former professional basketball player)
• Occupation: Professional Basketball Player (Shooting Guard)
• Team: Phoenix Suns (NBA)
• Career Highlights: Drafted 13th overall in the 2015 NBA draft. Three-time NBA All-Star, All-NBA First Team selection (2022), and an Olympic gold medalist with Team USA at the 2020 Tokyo Games. He signed a four-year, $220 million supermax contract extension with the Suns.
• Key Entities: Phoenix Suns, NBA, Team USA, Kevin Durant, Chris Paul, Supermax Contract, Kentucky Wildcats.

The On-Again, Off-Again Chronicle: A Complete Relationship Timeline

The relationship between Kendall and Devin is a masterclass in celebrity privacy mixed with high-profile public sightings. Their initial connection predates their official dating, adding a layer of complexity to their history.

May 2018: The First Link. The pair were first spotted together on a double date, but they were not with each other. Kendall was dating NBA player Ben Simmons, and Devin was with his then-girlfriend, Jordyn Woods (a former friend of the Kardashian-Jenner family). This early interaction established a social connection that would later blossom into romance.

April 2020: The Road Trip Rumors. During the initial COVID-19 lockdown, Kendall and Devin went on a road trip from Los Angeles to Arizona, a journey that first ignited dating speculation. They were seen together numerous times over the next few months, although sources insisted they were just friends.

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Valentine’s Day 2021: Going Instagram Official. After months of speculation, the couple finally confirmed their relationship by sharing sweet, intimate photos on their Instagram Stories for Valentine’s Day. This marked the start of their two-year, public-facing romance.

2021-2022: The Golden Era. Kendall became a regular fixture at Phoenix Suns games, offering public support during the team's run to the NBA Finals. They traveled together, including a notable trip to Italy, and shared glimpses of their life on social media, often celebrating milestones like their one-year anniversary and Devin's Olympic gold medal win.

June 2022: The First Breakup. Reports surfaced that the couple had broken up or were taking a break. Sources cited their demanding schedules and the difficulty of maintaining a serious relationship with their conflicting priorities.

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August 2022: The Reconciliation. The break was short-lived. By August, they were reportedly "fully back together," having worked out their issues and realizing they missed each other.

November 2022: The Definitive Split. Following a brief reconciliation, the couple officially split again, reportedly due to the same issues of scheduling and differing priorities. This breakup came shortly after Devin’s birthday.

Early 2023: The Bad Bunny Era. Kendall moved on and began a highly publicized relationship with Puerto Rican rapper Bad Bunny. This relationship lasted throughout 2023.

February 2024: The Quiet Rekindling. After Kendall and Bad Bunny called it quits in late 2023, reports began to surface that she was already reconnecting with Devin Booker. Sources indicated they were "slowly" rekindling their romance.

Late 2024/Early 2025: The NYC Sighting. The most recent and compelling evidence of their reunion is the sighting of both Kendall and Devin leaving the same hotel in New York City, suggesting their "slowly rekindling" phase has moved into a full-blown reunion.

7 Key Reasons Why They Keep Coming Back to Each Other

The pattern of breaking up and reuniting suggests a powerful, undeniable connection. The following are the most speculated reasons why the supermodel and the NBA superstar cannot seem to stay apart.

1. Unmatched Privacy and Low-Key Dynamic. Compared to other Kardashian-Jenner romances, Kendall and Devin’s relationship was notably private. They rarely discussed each other in the press and only occasionally shared moments on social media. This shared desire for a low-key relationship, away from the constant spotlight of the reality TV world, is a rare and valuable common ground.

2. Shared Understanding of High-Pressure Careers. Both individuals operate at the absolute peak of their respective industries. Devin deals with the intense pressure of the NBA, including his massive $220 million contract and the demands of the Phoenix Suns' championship aspirations. Kendall manages the global modeling circuit and her multi-million dollar business, 818 Tequila. Their mutual understanding of this intense professional life creates a unique empathy that few others can match.

3. The "Kardashian Curse" Exception. Kendall is the only member of the famous family who has not had a child. Furthermore, Devin Booker’s career has only soared since they started dating, completely defying the tabloid-driven "Kardashian Curse" narrative often applied to the men who date the sisters. This success factor may subconsciously reinforce the idea that their relationship is a positive force in their lives.

4. The Arizona Connection. The relationship began with a road trip to Arizona, the state where Devin is a star for the Phoenix Suns. Kendall has also spent significant time there, giving them a geographical anchor away from the relentless Los Angeles paparazzi and the *Kardashians* Hulu show set.

5. The Age and Life Stage Alignment. Born only a year apart, Kendall (1995) and Devin (1996) are at similar life stages. They share a youthful energy but also the maturity of being established, globally recognized professionals. This alignment in age and experience is a strong foundation for a long-term connection.

6. A Genuine, Deep Connection. Sources close to the couple have consistently described their bond as genuine and deeply rooted, not merely a fleeting celebrity fling. The fact that they keep attempting to make it work after multiple splits suggests the emotional connection is too strong to ignore, despite the logistical challenges.

7. Post-Bad Bunny Reflection. Kendall’s high-profile, yet ultimately brief, relationship with Bad Bunny may have provided the necessary perspective to realize what she valued in her connection with Devin. The period apart often serves as a catalyst for a mature reconciliation, where both parties are more willing to compromise on the issues that led to the initial breakups. This current reunion, fueled by sightings in early 2025, suggests a more intentional effort to make the relationship last.

What’s Next for the Supermodel and the Superstar?

The current status of Kendall Jenner and Devin Booker is one of cautious optimism. While they are reportedly back on, the lessons from their past—namely, the strain of their demanding careers—will undoubtedly test their renewed commitment. Fans and media alike will be watching closely to see if the latest chapter in their love story will finally lead to a permanent, stable relationship or if they are destined to remain one of Hollywood's most captivating, on-again, off-again couples.