Tristan Thompson’s dating life has been a constant source of media attention, particularly due to his tumultuous on-and-off relationship with reality TV star Khloé Kardashian. The Canadian NBA player, who currently plays for the Cleveland Cavaliers, has made headlines not just for his basketball prowess but for his complex romantic entanglements that have played out in the public eye for nearly a decade.
The 34-year-old athlete’s love life has been marked by controversy, infidelity scandals, and high-profile breakups that have fans and critics alike. From his early relationship with Jordan Craig to his well-documented romance with Khloé Kardashian, Thompson’s dating history reads like a Hollywood drama filled with cheating allegations, surprise pregnancies, and public reconciliations.
Most recently, Thompson has been spotted with a mysterious woman who bears a striking resemblance to Kim Kardashian, sparking fresh speculation about his current relationship status and dating preferences. This latest development has reportedly left his ex-girlfriend Khloé Kardashian feeling “very hurt,” according to insider sources. The sighting has reignited public interest in Thompson’s romantic life and raised questions about whether he has a particular type when it comes to choosing partners.
As Thompson continues to navigate co-parenting responsibilities with multiple women while maintaining his professional basketball career, his personal life remains under intense scrutiny. Understanding his dating history provides insight into the patterns and controversies that have defined his relationships over the years, from his early days in the NBA to his current status as a father of four children with three different women.
Early Relationship with Jordan Craig
Thompson’s first high-profile relationship was with Jordan Craig, which lasted from 2014 to 2016. Craig, a model and social media influencer, was Thompson’s girlfriend during his early years in the NBA. Their relationship appeared stable until it took a dramatic turn when Craig discovered she was pregnant with Thompson’s child after their breakup.
The timing of their split became controversial when it was revealed that Thompson had begun dating Khloé Kardashian in September 2016, while Craig was still pregnant with his son. Craig gave birth to their son, Princ,e in December 2016, and the circumstances surrounding the relationship’s end later became a source of public speculation and legal documentation.
Craig later questioned the timeline of events, particularly regarding when Thompson and Kardashian’s relationship actually began. She expressed concerns about whether Thompson had been unfaithful to her while she was pregnant, though Thompson publicly denied these allegations on social media.
The Khloé Kardashian Era
Thompson’s relationship with Khloé Kardashian began in September 2016 and quickly became one of the most scrutinized celebrity relationships in recent memory. The couple’s romance was initially casual, but it intensified rapidly, with their relationship becoming public knowledge within months of meeting.
The First Pregnancy and Cheating Scandal
In December 2017, Kardashian announced she was pregnant with Thompson’s child. However, their joy was short-lived when, just days before Kardashian was due to give birth, Thompson was caught on video being unfaithful with multiple women. Despite this devastating betrayal, Kardashian chose to stay with Thompson, and they welcomed their daughter True in April 2018.
The Jordyn Woods Incident
The couple’s relationship faced another major crisis in February 2019 when Thompson was caught cheating with Jordyn Woods, who was Kylie Jenner’s best friend and a close family friend of the Kardashians. This incident was particularly painful for the family as it involved someone they trusted, and it ultimately led to Woods being ostracized from the Kardashian circle.
Pandemic Reconciliation
During the COVID-19 pandemic in 2020, Thompson and Kardashian quarantined together while co-parenting True. This period of isolation led to a reconciliation, and they officially resumed their relationship from summer 2020 to June 2021. The couple even discussed having another child together during this time.
The Final Breakup
Their relationship ended definitively in December 2021 when it was revealed that Thompson had fathered a child with Maralee Nichols while he was still with Kardashian. Nichols gave birth to Thompson’s son Theo in December 2021, and Thompson confirmed his paternity in January 2022, issuing a public apology to Kardashian.
Despite this betrayal, Kardashian and Thompson welcomed their second child, Tatum, via surrogate in July 2022. The timing meant that Kardashian was expecting their second child when news of Thompson’s affair and third child broke.
Current Dating Status and Recent Developments
As of 2025, Thompson appears to be single, though he has been spotted with various women since his final split from Kardashian. Most notably, in August 2024, he was photographed at Giorgio Baldi, an upscale Italian restaurant in Santa Monica, with a mystery woman who bears a striking resemblance to Kim Kardashian.
The Kim Kardashian Look-Alike
The woman Thompson was spotted with has long black hair, sculpted features, and wears a body-hugging black dress with a Chanel handbag. The resemblance to Kim Kardashian was so striking that it immediately sparked media attention and speculation about Thompson’s dating preferences.
This development has reportedly been particularly painful for Khloé Kardashian, who sources say is “very hurt” by Thompson’s choice to date someone who looks like her sister. Insiders reveal that Kardashian has struggled to move on from Thompson despite his repeated infidelities and continues to have feelings for him.
Khloé’s Current Stance on Dating
Meanwhile, Khloé Kardashian has been open about her current relationship status, stating in early 2025 that she is not actively dating anyone. On her podcast “Khloe in Wonderland,” she explained that she’s focusing entirely on her children and co-parenting relationship with Thompson.
“I’ve chosen not to—because I genuinely don’t want to—I’m not dating,” Kardashian revealed, adding that her relationship with her children is everything to her. She acknowledged that while she’s open to love in the future, she’s not actively seeking it and feels fulfilled with her current situation.
Co-Parenting and Current Relationship Dynamics
Despite their tumultuous romantic history, Thompson and Kardashian have managed to establish a positive co-parenting relationship for their children True and Tatum. Kardashian has praised their current dynamic, stating that they “co-parent really well” and get along better now than they did during their romantic relationship.
“He did make mistakes,” Kardashian acknowledged in a 2024 interview, “He’s the nicest guy and we get along so well now. We’re not meant to be together, but he was meant to be the father of these kids.” This mature approach to co-parenting has allowed both parents to focus on their children’s well-being despite their complicated past.
Thompson is also a father to Prince with Jordan Craig and Theo with Maralee Nichols, making him a father of four children with three different women. Managing these multiple co-parenting relationships while maintaining his basketball career and personal life continues to be a significant aspect of his current situation.
