tristan thompson cheating scandal
maraleenichols via Instagram _Mitchell Layton / Contributor via Getty Images

A Look Back at All the Girls Tristan Thompson Has Dated

Culture

| LAST UPDATE 10/03/2022

By Tiana Blanco

Tristan Thompson's love life has made endless headlines over the years. From dating A-listers like Khloé Kardashian to the cheating allegations that soon followed, here's everyone the NBA star has been linked to.

Jordan Craig

Where it all started: before becoming a household name, Thomspon was busy dating lifestyle blogger Jordan Craig - between 2014 to 2016. They eventually called it quits sometime around the first half of 2016.

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@alleyesonjordyc via Instagram

While it's not clear why they ended things, before they split up, the pair found out that Craig was pregnant with the NBA star's child. And by December 2016, Tristan became a father for the very first time - though his time with his baby mama was far from over...

Baby Mama Drama

Two years after their son, Prince Oliver Thompson, was born, Craig and Tristan were still fighting over child support. Craig's argument to the court was that her baby daddy had only seen his child a total of nine times between  December 2016 and November 2018.

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@alleyesonjordyc via Instagram

Eventually, the parents settled things, and Tristan was ordered by a judge to pay Craig $40,000 dollars a month for child support. Moreso, he was also told he owed the 31-year-old $200,000 dollars in retroactive child support, based on reports from Us Weekly.

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Clearing the Air

Since it wasn't clear when Tristan and Craig broke up, rumors began spreading that he cheated on her with Khloé Kardashian, whom he started dating in August of 2016. "When I met Khloé, I was SINGLE," Tristan tried to clarify on Twitter. "The negative comments that are constantly being directed towards her are unnecessary."

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Joseph Okpako / Contributor via Getty Images

“My truth is: I met Tristan because HE CHOSE to go on a blind date with me. A mutual friend set us up,” Khloé tweeted. “After going on some dates, Tristan told me that he had an ex that was pregnant. Obviously, I was reluctant about us continuing to date or start a relationship.” But he assured that things were over with Craig.

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Larsa Pippen

The timeline confusion between when Tristan dated Craig vs. when he started things with Khloé became even more confusing when Kim Kardashian's ex-BFF, Larsa Pippen, entered the picture. She revealed that she was also dating the NBA star back in 2016 - right before he and Khloé got serious.

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Neilson Barnard / Staff via Getty Images / George Pimentel / Contributor via Getty Images

“I was kinda seeing Tristan before Khloé, before Khloé or any of [the Kardashians] knew he existed,” the Real Housewives of Miami star confessed during a podcast episode for the Hollywood Raw​​​ in November 2020. “I was seeing him, I had him come to L.A. I brought him to a party Kim had. I introduced him to all of them.”

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"It's Whatever"

According to Larsa, it was only 10 days later that the Chicago Bulls player and Khloé started seeing each other. But apparently, she wasn't fazed by the new couple. "I don't even care. It's whatever. I'm the type of person that doesn't chase what's not for me," she said.

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Jerritt Clark / Stringer via Getty Images

"I will never chase a man; I will never put a leash on a man. I don't do that. I feel like, let you be great. If you want to be with other people, go ahead. I'm great by myself." Despite her accusations, sources close to Khloé have denied that she ever met Tristan through Larsa... perhaps we'll never know the truth.

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Khloé Kardashian

No matter how Khloé met Tristan, the two obviously adored each other very much. Their relationship blossomed quite quickly. And in no time at all, they were already becoming Instagram official on Halloween 2016, showing off their Marvel superheroes Storm and Black Panther costumes.

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@khloekardashian via Instagram

For a while, things seemed great. The couple looked happy, and no drama surrounded their relationship. In January 2017, Khloé even released a blog post about it. "It's such a great feeling that I have my happy back! It's from a genuine place and the most peaceful place I've been in for longer than I can even remember," she wrote.

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Becoming a Dad, Again

By April 2017, the 38-year-old confessed that she could potentially see herself starting a family with her boo thang, Tristan. "We've talked about it. He [already] is a father, and I know for a fact that he would be an impeccable father," Khloé admitted.

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@khloekardashian via Instagram

"I definitely want to be a mom. But I don't put the pressure on it. It's not like, 'The clock is ticking.' I feel in my soul it will happen." Sure enough, only 8 months later, she announced to the world her pregnancy. Fans were happy to see Khloé finally getting everything she'd always wanted. Or so they thought.

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Cheating Rumors Emerge

April 2017 was a busy month for the couple, not only did they welcome their baby girl, True, but numerous cheating scandals began surfacing. A few days before Khloé gave birth, Daily Mail released a video of a mystery man kissing a random woman at a rooftop lounge.

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MEGA / Contributor via Getty Images

Said man was reported to have been Tristan with a woman who was not his baby mamma. Later on, photos of Tristan with the same woman, walking into a hotel room, started circulating. Clearly, this news started an overwhelming amount of drama. Was Tristan cheating on Khloé days before her due date?

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Delivery Room Drama

The cheating scandal shocked the world. But despite what fans were saying about Tristan, Khloé still had him in the delivery room when she gave birth on April 12, 2018. The reality star later defended her choice, "Regardless of what Tristan did to me, I was never going to take that moment away from True or Tristan."

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E! Entertainment via Youtube

"She should not be punished for his actions. He is her father, and they both deserve to love one another as deeply as they possibly can," she wrote on Twitter. Many thought that this meant they would split up and co-parent. But in May of that year, Khloé admitted they were trying to work things out.

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Lani Blair

Although the alleged cheating footage was released the same month that Khloé gave birth in April of 2018, it was said that the footage of Tristan with the mysterious woman at the hotel was taken back in October 2017. It was also revealed that said woman was model Lani Blair.

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@laniblair via Instagram / George Pimentel / Contributor via Getty Images

One witness who was reportedly there that night the infidelity took place shared details: "They were holding each other, and it was so obvious. Everybody knew who he was. We talked about it, and everybody watched them make out several times." All while his girlfriend was pregnant...

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Jordyn Woods

Arguably one of Hollywood's biggest scandals occurred in February 2019 when a close pal of the Kardashian family was spotted making out with Tristan. Jordyn Woods was Khloé younger sister, Kylie Jenner's best friend for years. The two were so inseparable that Jordyn even lived in Jenner's house.

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@jordynwoods via Instagram / Maddie Meyer / Staff via Getty Images

It seemed like nothing could break their bond... that was until news that Jordyn and Tristan were together at a party was leaked. Not only was it shocking that Tristan was once again cheating on Khloé, but fans were in disbelief that it was with someone so close to her.

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"It Hurts Even More"

The news first broke when Jordyn herself actually called Khloé to tell her she was at Tristan's party. Things weren't clear, but after Hollywood Unlocked's Jason Lee called Kim Kardashian's former friend, Larsa Pippen, the truth about what happened that night was revealed. Jordyn had kissed the NBA star.

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Hollywood To You/Star Max / Contributor via Getty Images

The incident not only caused Tristan and Khloé to break up yet again, but it broke the reality TV star's heart. "This time, it hurts even more because the person who it was with is someone who knows very much what Khloé has gone through in the past year. Jordyn is like part of the family," an insider close to KoKo revealed.

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Cutting All Ties

Khloé said during a KUWTK episode, "He [Tristan] answered my questions, and I got more details - that everybody left the party and Jordyn stayed, that she was sitting on his lap, they were all over each other, they were handsy, they made out. It's disgusting. I'll never understand the depths of his... ugh."

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@jordynwoods via Instagram

"I was just hoping for a better outcome for my daughter and myself," KoKo added. But her baby daddy wasn't the only one she was mad at. She, Kylie, and the rest of the family ended up cutting all ties with Jordyn. It was a media frenzy for all of them. And honesty, fans couldn't get enough.

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Jordyn's Red Table Talk

So when Jordyn appeared on Jada Smith's show Red Table Talk, thousands of people tuned in to hear her side of the scandalous story. "I was drunk, but I was not beyond the point of recollection. I know where I was. But on the way out, he did kiss me. No passion, no nothing, on the way out. He just kissed me."

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Red Table Talk via Facebook

Tensions were high for a bit, but after 2 years, things had settled down, and Khloé even said there were no hard feelings. "I don't have any grudge against Jordyn. I think people make mistakes, people live, and they learn, and I forgive both parties. How could I forgive Tristan and not Jordyn?" she admitted.

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Karizma Ramirez

After cheating on her two times and after the outrageous Jordyn scandal, Khloé eventually called it quits with Tristan. The two decided that while they weren't going to date, they would be civil and co-parent their daughter True, who at the time was a few months away from turning one.

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@karizmaaa.__ via Instagram /George Pimentel / Contributor via Getty Images

The basketball player wasted no time after the breakup. That same month, in February 2019, he was linked with model Karizma Ramirez after the two were seen grabbing dinner in New York City. But it turned out to be a short fling because, by March, they were already over.

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Kimberly Alexander

Following the major scandal, things between Tristan and Khloé remained private for a year. During this time in May 2020, Tristan dealt with a lawsuit he filed against a woman named Kimberly Alexander after she claimed her 4-year-old son was the NBA star's.

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@kimcakery305 via Instagram / George Pimentel / Contributor via Getty Images

He denied fathering the child and was even willing to give a paternity test in January of that same year, which “conclusively determined that Thompson is not the father of Alexander’s child.” But Alexander “refused to accept the results,” and she even accused Tristan and Khloé of “manipulating the results.”

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Back to Khloé

The beginning of 2020 probably pushed the couple back together: not only did Khloé stand by Tristan's side through the false paternity accusation, but the two parents also celebrated True's 2nd birthday in April. So by the summertime of that year, they were reported to have been trying to work things out.

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@realtristan13 via Instagram

Based on reports from People magazine, "Tristan is working hard to prove himself and has been a great dad to True." The source also revealed to the magazine, "She loves having him around. He has the best relationship with True. And he has been amazing to Khloé too. They are very much together, and Khloé is beyond happy."

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Engagement Rumors

For a few months, KoKo and Tristan kept things on the down low. So when Khloé shared a photo promoting her brand Good American's new shoe line in February 2021, fans were surprised to see her wearing a giant rock on her left ring finger. Could the couple be engaged?

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@khloekardashian via Instagram

Well, as it turned out, the fans were too quick to assume: the ring she was wearing wasn't even purchased by the NBA basketball player. But even though they weren't getting married, a source reported to Entertainment Tonight that the duo was "stronger than ever."

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The Ultimate Birthday Surprise

In March 2021, 2 years since the cheating scandal, Khloé revealed the couple was solid. To celebrate, she even threw him a 30th birthday bash. "The ones that are meant to be are the ones who go through everything that is designed to tear them apart, and they come out even stronger than they were before," the caption read.

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@khloekardashian via Instagram

Unfortunately, Tristan later admitted in court documents that that same night, he went and hooked up with a different woman whom he ended up impregnating. And while this news wasn't revealed to the public until months later, the paternity lawsuit was filed by June of that year.

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Sydney Chase

To the public, it seemed like everything was finally working out for Khloé and Tristan. But behind closed doors, the NBA star wasn't being faithful. The same month that engagement rumors started spreading, a woman named Sydney Chase came out claiming she had slept with Tristan.

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@sydneychasexo via Instagram /George Pimentel / Contributor via Getty Images

The Instagram model admitted on the No Jumper podcast that back in November of 2020, she and the NBA star had an intimate relationship. They continued hanging out up until January of 2021. "I did not know he was in a relationship. He told me he was not in a relationship anymore," she said.

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“That’s When Everything Started”

After what Sydney said during the interview, the internet went wild with questions. Luckily, the model wasn't afraid of telling her truth because she revealed in the comment section of one of her TikTok videos that the last time she and Tristan spoke was the day after KoKo threw a party for True.

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@sydneychasexo via Instagram

"We did have past relations, I then found out he was in a relationship, and I ended things. In the interview, things got misconstrued while we were drinking," she clarified. "We first met on November 11, to be exact, and that's when everything started."

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Cease and Desist

Things got heated when a past Instagram Live Sydney hosted had resurfaced. In the clip, she was seen to have been reading out loud text messages between herself and Tristan. In one message, she claimed that the basketball player told her that Khloé just was "not his type."

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@sydneychasexo via Instagram

This led to Tristan's lawyer sending Sydney a cease and desist that said her allegations were "malicious, defamatory fabrications" and that the two had "no relationship whatsoever." She then wrote on Instagram, "Let this be a lesson to not let anyone, no matter the money or fame they have, shut you down or tarnish your name."

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Maralee Nichols

In June 2021, a woman named Maralee Nichols filed a lawsuit against Tristan, claiming that she was pregnant with his child. This drama was all happening behind closed doors until December of that year, when the personal trainer gave birth to her son, Theo.

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@maraleenichols via Instagram/Mitchell Layton / Contributor via Getty Images

It was later revealed through a paternity test in January that Tristan was indeed the child's father. The media went wild - when could he have had relations with this woman if he was back with Khloé? The NBA star ended up admitting he was intimate with the woman on his 30th birthday in March of 2021.

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Taking Responsibility

More information surrounding Tristan and Maralee was revealed through the documents. Apparently, the pair first met back in December 2020 and continued seeing each other until March of the following year. But Tristan claimed they didn't have a "serious, ongoing relationship" - they just hung out "sporadically."

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Jason Miller / Stringer via Getty Images

When the truth became public, Tristan wrote on Instagram, “I take full responsibility for my actions. Now that paternity has been established, I look forward to amicably raising our son,” he added. “I sincerely apologize to everyone I’ve hurt or disappointed throughout this ordeal, both publicly and privately.”

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Hush Money

According to Page Six, Maralee went to court to sue Tristan for child support as well as for reimbursement of medical expenses. She also requested payment for pregnancy-related costs, as the athlete begged her to terminate the pregnancy so no one would find out.

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@maraleenichols via Instagram

He apparently even went as far as to offer her $75k to keep quiet. But eventually, he agreed to raise the baby with her. Well, or so we thought. "Thompson has done nothing to support their son. He has not made any attempt to meet their son, nor has he provided any financial assistance," her representative told People.

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“All of That Was a Lie”

Fans might have been in disbelief that Tristan impregnated another woman, but not as much as Khloé was. Because according to her, she found out about the paternity suit "with the rest of the world." Her older sister Kim actually told her the news after reading it herself on The Daily Mail.

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Keeping Up With The Kardashians via Youtube

On an episode of The Kardashians, KoKo complained how Tristan didn't give her a "heads up" before it came out. "It's just an additional slap in my face. It's humiliating, I'm embarrassed. I am replaying every event, every grand gesture, every trip, every date. All of that was a lie. How were you able to not saying something?"

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Coming Clean

In January 2022, Tristan took to Instagram to publicly apologize to Khloé for cheating on her yet again. "You don't deserve the heartache and humiliation I have caused you. You don't deserve the way I have treated you over the years," he said, referring to his scandal with Jordyn and the videos of him with another woman.

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Keeping Up With The Kardashians via Youtube

"My actions certainly have not lined up with the way I view you. I have the utmost respect and love for you," the NBA basketball star assured. "Regardless of what you may think. Again, I am so incredibly sorry." But the apology wasn't enough because Khloé ended things with Tristan.

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Surrogate Bombshell

Things seemed calm for a while after Tristan and KoKo's break up. But that was just the calm before the storm because, in July 2020, it was announced that the couple was expecting their second child together - via surrogate. A representative of The Kardashians star told Page Six, "We can confirm True will have a sibling."

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Shutterstock

"Khloé is incredibly grateful to the extraordinary surrogate for such a beautiful blessing. We'd like to ask for kindness and privacy so that Khloé can focus on her family." Fans were confused: how and when could this have happened if the pair were split up?

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Co-Parenting

As it turned out, it was in November, just one month before the news of Maralee's pregnancy was revealed, that Khloé and Tristan conceived their child. And ever since, the two have been separated. In fact, according to Insider, a source revealed they don't speak "outside of co-parenting matters."

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@realtristan13 via Instagram

During an interview with ABC News that occurred in April, Khloe confessed that she is officially forever done with her baby daddy. "With Tristan, I did feel incredibly safe in the beginning, and I felt really good for a time," she added. "I still think he's a great guy, and he's a great dad, he's just not the guy for me."

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The Saga Continues...

A few weeks after the announcement of Tristan and Khloe's second child, he was caught red-handed.. again. And while this time, he is a single man, fans were still in awe that he was so fast to find a new woman. A video that went viral showed the basketball star holding hands with a mystery woman in Mykonos, Greece.

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TMZ via Youtube

The clip was filmed by a fan, but more information about it was later revealed. He was supposedly out partying all night at a club named Bonbonniere before being seen with the woman at 5 am, based on reports from TMZ. We guess we'll have to wait and see how this next saga plays out...

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