Tristan Thompson's girlfriends & alleged flings: from Khloé Kardashian to Sydney Chase

5 May 2021, 09:48

Tristan Thompson dating history: girlfriends & alleged flings from Khloe Kardashian to Sydney Chase
Tristan Thompson dating history: girlfriends & alleged flings from Khloe Kardashian to Sydney Chase. Picture: Getty

Are Khloé Kardashian and Tristan Thompson together? Who are his ex-girlfriends and alleged flings?

Tristan Thompson and his most high-profile girlfriend to date, Khloe Kardashian, have faced their fair share of public ups and downs during their on-off relationship, mainly surrounding a number of cheating scandals involving the NBA player.

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As of 2021, it appears the couple have reconciled after quarantining together during the pandemic with their three-year-old daughter, True. However, a fresh batch of claims accusing Thompson of being unfaithful again may have rocked their romance once more.

Model Sydney Chase alleges she began hooking up with Tristan at the end of 2020 and into the new year, adding that he told her he was "single". Khloe and Tristan are yet to respond to the allegations.

So, who has Tristan dated in the past? Who are his ex-girlfriends and who has been been romantically linked to?

  1. Khloe Kardashian

    Tristan has been accused of cheating on Khloe multiple times during their on-off relationship.
    Tristan has been accused of cheating on Khloe multiple times during their on-off relationship. Picture: Getty

    Tristan and Khloe were first spotted together in August 2016 after being introduced by a mutual friend. They confirmed their relationship two months later on Halloween, dressing up as Marvel superheroes Storm and Black Panther.

    In December 2016, Tristan's ex-girlfriend Jordan Craig gave birth to his son, Prince Oliver, igniting speculation that Khloe was the reason for their split. Jordan has since insinuated that this was the case, while Khloe has denied it. She once tweeted, "he never left ANYONE for me."

    A year into their relationship, news broke that the couple were expecting their first child together, with Khloe confirming her pregnancy in December 2017.

    However, just days before her due date, TMZ shared footage appearing to show Thompson kissing another woman at a rooftop lounge in New York. He was later photographed entering a hotel with her. Another video then leaked reported to be Thompson kissing two other women at a hookah lounge.

    Khloe gave birth to their daughter True Thompson on April 12, 2018. In the following months, it was reported that Khloe and Tristan were 'rebuilding' their relationship.

    Khloe and Tristan have been on and off since August 2016.
    Khloe and Tristan have been on and off since August 2016. Picture: Instagram/@khloekardashian

    In February 2019, shortly after reports that Khloe and Tristan had broken up, Thompson was accused of hooking up with Kylie Jenner's best friend Jordyn Woods at a house party. A month later, on an episode of Red Table Talk, Jordyn claimed Tristan kissed her as she was leaving a party at his house.

    Khloe fired back on social media - even brandishing Woods a "liar" on KUWTK - and the once close relationship between Jordyn and the Kardashian-Jenners was broken for good.

    In the year following, Khloe and Tristan remained very private about the state of their relationship, with Tristan occasionally shouting out Khloe on social media and hinting that the pair were on good terms.

    In April 2020, Khloe said she was considering using Thompson as a sperm donor for another child. It's been reported that the pair rekindled their romance that summer.

    A year later, Khloe was spotted sporting a huge diamond on her ring finger, sparking engagement rumours at the time. These were soon overshadowed by rumours of Tristan cheating on Khloe with Instagram model Sydney Chase.

  2. Sydney Chase

    Sydney alleged she first hooked up with Tristan in November 2020.
    Sydney alleged she first hooked up with Tristan in November 2020. Picture: Instagram/@sydneychasexo

    In April 2021, model Sydney Chase claimed she had hooked up with Tristan after first meeting in November 2020.

    Chase dropped the bombshell during an appearance on the No Jumper podcast, alleging that she was sexually involved with the sports star in January this year. She also claimed he told her he was single.

    "I did not know he was in a relationship. He told me he was not in a relationship anymore," she said, adding that the pair had 'hung out' on multiple occasions.

    After her interview went viral, Sydney clarified her comments in a TikTok video and claimed she last heard from Thompson the day after Khloe Kardashian threw a party for their daughter True.

    "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 said.

    "We first met in November 11 to be exact and that's when everything started. And then the last time we had contact - besides when he messaged me after finding out about the interview - was the day after his daughter's birthday party when he just got back home from Boston."

    In an uncovered Instagram Live from early April, Sydney is repotted to have read aloud text messages she allegedly received from Thompson, including one where he said Khloe was "not his type."

    Sydney later posted and deleted screenshots allegedly showing Khloe reaching out to her via Instagram, asking for their chat to remain confidential.

    At the beginning of May, Tristan's lawyer reportedly sent Sydney a cease and desist over the allegations, which she denied.

    The letter described Sydney's claims as ‘malicious defamatory fabrications’, stating they had ‘no relationship whatsoever’ and no such texts were exchanged.

    Sydney responded to the letter with a statement on Instagram, writing, "Let this be a lesson to not let anyone no matter the money or fame they have, to shut you down or tarnish your name."

  3. Jordyn Woods

    Thompson kissed Jordyn after an after-party at his house in early 2019.
    Thompson kissed Jordyn after an after-party at his house in early 2019. Picture: Instagram/@jordynwoods

    As previously mentioned, Jordyn Woods was at the centre of one of the biggest celebrity cheating scandals in recent years.

    Woods had long-been best friends with Khloe's younger half-sister Kylie Jenner at the time the story broke of her alleged fling with Thompson, making it headline news.

    It was first reported that the pair had kissed, slept together and even engaged in a month-long relationship - most of which was denied by Woods during her appearance on Red Table Talk.

    Woods confirmed that she did attend an after-party at Thompson's house, before claiming he kissed her as she was leaving in the early hours of the morning. She later took a lie detector test to prove she didn't sleep with him, with the polygraph results confirming that she didn't.

    The Kardashian-Jenner family have since cut all ties with Woods, while Thompson has never directly spoken about the incident.

  4. Lani Blair

    Lani Blair allegedly hooked up with Tristan in New York while he was in a relationship with Khloe.
    Lani Blair allegedly hooked up with Tristan in New York while he was in a relationship with Khloe. Picture: Instagram/@laniblair

    In 2018, Tristan was accused of cheating on Khloe with model Lani Blair while Khloe was pregnant with his child.

    Just days before Khloe went into labour, footage leaked online which reportedly showed Thompson kissing Blair at a rooftop bar in New York, before being photographed entering a hotel with her.

    A witness said at the time, "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."

  5. Jordan Craig

    Tristan's ex-girlfriend Jordan gave birth to their son, Prince, in December 2016.
    Tristan's ex-girlfriend Jordan gave birth to their son, Prince, in December 2016. Picture: Instagram/@alleyesonjordyc

    Tristan and his ex-girlfriend Jordan Craig dated for two years from 2014 until their split in 2016. She gave birth to the Thompson's first child, a son named Prince Oliver, in December 2016.

    It's unclear when Tristan and lifestyle blogger Jordan broke up, but it's thought to have occurred around the first half of 2016. Thompson started dating Khloe in August 2016.

    Jordan, who is first cousins with Kevin Hart's wife Eniko Parrish, has previously suggested that there was an overlap between her relationship with Tristan and Khloe's. Both Tristan and Khloe and vehemently denied this, stating that they were both single at the time they started dating.

    "When I met Khloe I was SINGLE," Thompson tweeted in July 2019. "The negative comments that are constantly being directed towards her are unnecessary.

    "She does not deserve all this backlash for my wrongdoings. Both Khloe and Jordan have been nothing but great mothers to my kids."

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