Kendall Jenner’s dating life has been a rollercoaster of high-profile relationships, breakups, and reconciliations that have kept fans and media outlets guessing for years. As the most private member of the Kardashian-Jenner clan when it comes to romance, the 29-year-old supermodel has managed to maintain an air of mystery around her personal relationships while still generating significant public interest.
Unlike her sisters who often share intimate details of their romantic lives on social media and reality television, Kendall has consistently chosen to keep her relationships largely out of the spotlight. This approach has made every look into her love life all the more intriguing for fans who eagerly follow her romantic journey.
The model’s most notable relationships have included NBA star Devin Booker and Puerto Rican rapper Bad Bunny, both of whom she has dated multiple times in an on-again, off-again pattern that has become characteristic of her romantic history. Her relationship timeline reads like a complex web of reconciliations, breakups, and new beginnings that span several years.
Currently, Kendall’s relationship status appears to be single following her most recent breakup with Devin Booker, though the pair’s history suggests this may not be permanent. Their pattern of reconnecting after periods apart has become a defining feature of their relationship, leaving fans wondering if another reconciliation might be on the horizon.
The Devin Booker Saga: A Five-Year On-and-Off Romance
The Beginning of Their Love Story
Kendall Jenner and Devin Booker’s relationship began in April 2020 when they were first photographed together on a road trip to Sedona, Arizona. The Phoenix Suns player, now 28, initially kept things casual with the model, but their connection proved to have staying power despite numerous obstacles along the way.
The couple didn’t make their relationship Instagram official until Valentine’s Day 2021, when Kendall shared a rare photo of them together on her Instagram Story with a simple white heart emoji. This public acknowledgment was significant given Kendall’s typically private approach to relationships, signaling that their connection had become more serious.
Their Most Recent Reconciliation and Breakup
After rekindling their romance in February 2025, sources confirmed that Kendall and Devin were “very much together” and appeared to be in a solid place. The couple was spotted being affectionate at a friend’s dinner party in New York City and spent Valentine’s Day weekend together in Aspen, Colorado.
However, their latest attempt at love was short-lived. By June 2025, the couple had quietly broken up “over a month ago,” according to sources who cited “communication issues” as the primary reason for their split. The insider explained that their busy schedules and inability to stay “on the same page” ultimately led to another breakup in their tumultuous relationship history.
The Pattern of Breakups and Reconciliations
Kendall and Devin’s relationship has been characterized by multiple breakups and reconciliations over their five-year history. Their first major split occurred in June 2022 after two years together, with sources citing that they were “on different paths.” However, they reconciled briefly before breaking up again in October 2022.
The couple explored dating again in February 2024, though they weren’t exclusive initially. This reconciliation came after Kendall’s relationship with Bad Bunny had ended, and friends reportedly hoped she would reunite with Devin, believing he made her happiest.
The Bad Bunny Interlude: A High-Profile Romance
Their First Relationship
Between her on-and-off relationship with Devin Booker, Kendall dated Puerto Rican rapper Bad Bunny from February 2023 to December 2023. Their relationship began when they were spotted making out at a private Los Angeles club, and it quickly became a fan favorite pairing.
The couple attended high-profile events together, including the Met Gala, and were frequently photographed on dates throughout 2023. Despite their chemistry, busy schedules, and Bad Bunny’s world tour plans ultimately led to their split in December 2023.
Their Brief 2024 Reunion
Kendall and Bad Bunny rekindled their romance in May 2024 after being spotted together at a Met Gala afterparty. Their reunion was described as passionate, with sources noting their “crazy attraction to each other.” However, this second attempt at love was even shorter-lived than their first, ending by September 2024.
The timeline of Kendall’s relationships during this period was particularly complex, as she was simultaneously exploring a reconciliation with Devin Booker while dating Bad Bunny. This overlap created tension, with sources noting that Bad Bunny “had not been happy” about her reconnecting with Devin.
Kendall’s Dating Philosophy and Approach to Love
Her Commitment to Privacy
Throughout all her relationships, Kendall has maintained her preference for keeping her romantic life private. Sources consistently note that she and her partners “like to keep their relationship private” but are “very touchy-feely when they’re with friends.”
This approach differs significantly from her famous sisters, who often share relationship details publicly. Kendall’s commitment to privacy has made her relationships more mysterious and, arguably, more intriguing to the public.
Her Philosophy on Love and Relationships
In a 2023 interview, Kendall revealed her approach to love, stating, “I love really hard, and I love without apology. I don’t like goodbyes, and I will fight to not have to say goodbye.” She emphasized that she “will always fight for relationships” and doesn’t “give up on anything.”
This philosophy helps explain the pattern of reconciliations in her romantic history, particularly with Devin Booker. Her willingness to give relationships multiple chances has resulted in the complex on-and-off dynamic that has characterized her most significant relationships.
Current Relationship Status and Future Prospects
Single and Focusing on Herself
As of June 2025, Kendall Jenner appears to be single following her latest breakup with Devin Booker. Sources suggest that she may be focusing on her career and personal growth during this period, similar to her approach in late 2024 when she expressed wanting to “stay single for now.”
Potential for Future Reconciliations
Given the pattern of her relationship with Devin Booker, fans and media outlets continue to speculate about the possibility of another reconciliation. Their five-year history of breaking up and getting back together suggests that their story may not be over, though only time will tell if they can overcome their communication issues and scheduling conflicts.
Marriage and Family Plans
When asked about marriage plans, Kendall’s mother, Kris Jenne,r stated that the family has “no marriage plans — yet.” However, Kendall has expressed interest in having children someday, mentioning that she would like “three max” but would be “cool with two.” Whether these future plans will include Devin Booker or someone new remains to be seen.
