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
Kendall Jenner and Devin Booker (Image via Getty)
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
Kendall Jenner and Bad Bunny (Image via Getty)
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
Kendall Jenner (Image via Getty)
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.
Colin Farrell, the charismatic Irish actor who has audiences worldwide with his magnetic screen presence, remains one of Hollywood’s most intriguing leading men. From his breakout roles in films like “Tigerland” to his recent acclaimed performances in “The Banshees of Inisherin” and “The Batman,” Farrell has consistently demonstrated his versatility as an actor. However, beyond his professional achievements, fans have always been fascinated by his personal life, particularly his romantic relationships. The question “Who is Colin Farrell dating?” has been a constant source of curiosity among entertainment enthusiasts and media outlets alike.
Currently, Colin Farrell is single and not in a relationship with anyone. This marks a significant shift for the actor, who was previously in a long-term relationship with Kelly MacNamara that lasted five years before ending in early 2023. The 49-year-old actor has been focusing on his career and his role as a father to his two sons, James Padraig Farrell and Henry Tadeusz Farrell. His current single status comes after a period of intense professional commitments, including his transformative role as the Penguin in “The Batman” and his award-winning performance in “The Banshees of Inisherin.”
Farrell’s approach to relationships has evolved significantly over the years, transitioning from his earlier days as Hollywood’s notorious bachelor to a more private and family-focused individual. His journey through love, heartbreak, and personal growth reflects the maturation of both his personal life and professional career, making his current relationship status all the more intriguing to fans and followers.
Colin Farrell’s Current Relationship Status
Colin Farrell (Image via Getty)
As of 2024, Colin Farrell is officially single and not dating anyone. This represents a notable change from his previous long-term relationship with Kelly MacNamara, which concluded in early 2023 after five years together. The end of this relationship marked the conclusion of one of Farrell’s most stable and enduring romantic partnerships in recent years.
The actor’s current single status appears to be a conscious choice, allowing him to focus on his flourishing career and his responsibilities as a father. Farrell has two sons from previous relationships: James Padraig Farrell, born in 2003 with American model Kim Bordenave, and Henry Tadeusz Farrell, born in 2009 with Polish actress Alicja Bachleda-Curuś. His dedication to fatherhood has become increasingly evident in recent interviews and public appearances.
Professional Priorities and Personal Growth
Farrell’s current single status coincides with one of the most successful periods of his career. His recent performances have garnered critical acclaim and numerous awards, including a Golden Globe for his role in “The Penguin” HBO series. This professional renaissance may have influenced his decision to remain unattached, allowing him to fully commit to his craft and upcoming projects.
The Kelly MacNamara Relationship: A Five-Year Journey
Colin Farrell’s most recent significant relationship was with Kelly MacNamara, which lasted from 2017 to early 2023. MacNamara, who works for U2 guitarist The Edge, maintained a relatively low profile throughout their relationship, which aligned with Farrell’s desire for more privacy in his personal life.
The relationship faced challenges due to both partners’ demanding work schedules. Farrell had previously described their dynamic, saying, “My girlfriend, she travels a lot for work, so we often cross two ships at night. But we make sure we find a port where we can meet.” This poetic description highlighted the difficulties of maintaining a relationship in the entertainment industry.
Reasons for the Split
The end of Farrell’s relationship with MacNamara was attributed to the pressures of his increasingly busy career schedule. His involvement in major productions like “The Banshees of Inisherin” and “The Batman” required extensive time commitments that ultimately affected their relationship. Sources indicated that there was no animosity between them, but the practical challenges of maintaining a romantic relationship while managing demanding work schedules became insurmountable.
Colin Farrell’s Extensive Dating History
Colin Farrell (Image via Getty)
Colin Farrell’s romantic history reads like a who’s who of Hollywood, spanning over two decades and including relationships with some of the entertainment industry’s most prominent figures. His dating history includes both confirmed relationships and rumored connections with numerous celebrities.
High-Profile Relationships and Rumored Romances
Farrell’s romantic connections have included relationships with Amelia Warner, Britney Spears, Nicole Narain, Angelina Jolie, Lindsay Lohan, Elizabeth Taylor, Carmen Electra, Rihanna, Michelle Rodriguez, Lake Bell, Maeve Quinlan, and Demi Moore. His brief marriage to Amelia Warner in 2001, though non-legally binding, marked one of his most publicized early relationships.
One of the most intriguing aspects of Farrell’s dating history was his relationship with screen legend Elizabeth Taylor, which he revealed in a 2013 interview with Ellen DeGeneres, though he noted it was “never consummated.” This connection demonstrated Farrell’s appeal across different generations and his ability to form meaningful connections with diverse personalities.
Significant Long-Term Relationships
Beyond the celebrity connections, Farrell has had several meaningful long-term relationships that resulted in children and deeper personal connections. His relationship with Kim Bordenave lasted two years and resulted in the birth of his eldest son, James. Similarly, his relationship with Alicja Bachleda-Curuś, his co-star in “Ondine,” lasted from 2009 to 2010 and produced his second son, Henry.
Fatherhood and Personal Transformation
Colin Farrell’s role as a father has been transformative in his personal life and has significantly influenced his approach to relationships. He has two sons: James Padraig Farrell, who was born with Angelman syndrome, a rare genetic disorder, and Henry Tadeusz Farrell. Farrell has been open about the challenges and joys of fatherhood, particularly in caring for a child with special needs.
Impact on Relationship Choices
Fatherhood has clearly influenced Farrell’s relationship decisions and priorities. His commitment to his sons’ well-being has become a central focus of his life, and this responsibility has shaped his approach to romantic relationships. The actor has spoken about how his sobriety, which he has maintained since 2006, was largely motivated by his desire to be a better father.
Career Renaissance and Future Prospects
Colin Farrell (Image via Getty)
Colin Farrell’s current single status coincides with a remarkable career renaissance. His recent performances in “The Banshees of Inisherin,” “The Batman,” and “The Penguin” have earned him critical acclaim and numerous awards. This professional success may be contributing to his current focus on career over romantic relationships.
Upcoming Projects and Time Commitments
With several high-profile projects in development, including “The Batman Part II” and “A Big Bold Beautiful Journey” with Margot Robbie, Farrell’s schedule remains demanding. These professional commitments may continue to influence his personal life choices and relationship availability.
A New Chapter for Colin Farrell
Colin Farrell’s current single status represents a new chapter in the life of one of Hollywood’s most compelling actors. While he remains unattached romantically, his focus on fatherhood, career excellence, and personal growth suggests a mature approach to life that prioritizes meaningful connections over fleeting relationships. As fans continue to follow his professional achievements and personal journey, the question of who Colin Farrell might date next remains open, but his current contentment with single life suggests he’s in no rush to change his relationship status.
