The Timeline Of Khloé & Tristan's Relationship Is So Dramatic

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Oof. This one is messy. Since their (love?) story began back in 2016, Khloé Kardashian and Tristan Thompson have had their fair share of um... Thompson’s wandering eye and tendency to father other people’s children. Troé most recently broke up in June 2021 but even broken up, these two are still making headlines together. After all the cheating, breakups, and paternity scandal, Thompson and Kardashian welcomed their second child together on August 5. Because obviously.

OK, OK, there’s context for that one. A representative for Kardashian told Elite Daily that this child was conceived before anyone knew about Thompson’s personal-trainer-paternity mishap. Still, I get exhausted trying to follow this romantic/parenting journey.

But hey, somewhere before — and in between — Jordyn Woods and Maralee Nichols, Troé had some happy moments! After all, there was a time when she said, “Thank you for treating me like a Queen!” and a time when he said, “You deserve the world Koko!” Yeahhh, those times feel pretty distant now. These days, Kardashian’s very moved on, Thompson’s reportedly “jealous,” and somehow the two are navigating coparenting.

Needless to say, the timeline of Khloé Kardashian and Tristan Thompson’s relationship is ~quite~ dramatic.

Pre-August 2016: Kardashian Gets Set Up With Thompson

Kardashian was set up with Thompson by their mutual friend, Brandon Jennings, but she was wary at first about whether or not they'd hit it off since she wasn't a fan of blind dates.

"I was at the Bel-Air hotel. [Tristan] came to the dinner because I didn't want to go on a blind date, so [my friend] Brandon kind of ambushed the blind date," she revealed during the Keeping Up With the Kardashians 10th Year Anniversary Special. "So, I had a bunch of people and he brought him and we just connected."

September 2016: Getting To Know Each Other

Thompson and Kardashian were first spotted together leaving Bootsy Bellows nightclub in Beverly Hills on Sept. 2, and, from there, they went from 0 to 100 pretty quickly. Days later, the two jetted off to Cabo San Lucas, Mexico for a romantic Labor Day getaway.

October 31, 2016: Social Media Official

Nothing says Instagram official like couples costumes. Kardashian confirmed her relationship on Twitter, captioning a photo of her and Thompson dressed as superheroes with a red heart emoji.

December 2016: A Merry Christmas & A Happy New Year Together.

If there was any doubt Kardashian and Thompson had taken their relationship to the next level, the fact they spent the holidays together (and couldn't stop gushing about it on the 'Gram) made things perfectly clear. Thompson vocalized his feelings for Kardashian in a sweet Christmas post, writing, "Merry Christmas & Happy Holidays from me and mines, to you and yours."

And by New Years, there was no denying they were a full-blown couple. Kardashian posted a snap of the pair sharing a moment on the dance floor during their New Year's festivities at Rockwell club in Miami.

April 2017: Thinking About Their Future

Kardashian revealed she and Thompson were already discussing the possibility of starting a family in an interview with The Evening Standard. "We've talked about it," Kardashian said. "He [already] is a father and I know for a fact that he would be an impeccable father. 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."

September 2017: Baby on Board!

Just a few months after Kardashian gushed about possibly starting a family with Thompson, Us Weekly reported she and Thompson were expecting their first child together.

December 2017: Kardashian Confirms Pregnancy

Three months after the initial pregnancy rumors broke, Kardashian took to Instagram with an emotional message confirming the news.

"My greatest dream realized!" Kardashian captioned a photo of Thompson cradling her baby bump. "We are having a baby! I had been waiting and wondering but God had a plan all along. He knew what He was doing. I simply had to trust in Him and be patient. I still at times can't believe that our love created life! Tristan, thank you for loving me the way that you do! Thank you for treating me like a Queen! Thank you for making me feel beautiful at all stages! Tristan, most of all, Thank you for making me a MOMMY!!! You have made this experience even more magical than I could have envisioned! I will never forget how wonderful you've been to me during this time!"

March 2018: Baby Shower Vibes

Kardashian and Thompson looked lucky in love as they celebrated the impending arrival of their daughter surrounded by family and friends. The extravaganza was full of balloons, flowers, and all things pink. Little did they know, their whole worlds were about to be turned upside down — and not just because of the new baby.

April 10, 2018: The Drama Begins

Just days before Kardashian would give birth to baby True, video footage of Thompson seemingly kissing other women at a club in Washington, D.C. — while Kardashian was at home pregnant — was released by TMZ.

April 12, 2018: Baby Makes Three

Despite calls from her sisters and her fans to dump Thompson over the cheating scandal, Kardashian allowed him to be in the delivery room when she gave birth to True.

The footage later aired on Season 15 of KUWTK. "Regardless of what Tristan did to me, I was never going to take that moment away from True or Tristan," she tweeted about the episode. "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."

April 2018-February 2019: Sorting Things Out

Kardashian and Thompson did their best to make their relationship work following his cheating scandal. Kardashian addressed their relationship on Twitter in June 2018, defending her decision to stay with him.

"You have no knowledge of what goes on in our household or the enormous rebuilding this takes to even coexist," she tweeted to a fan. "I’m proud of my strength. I appreciate your opinion and I hope you hold that same opinion to everyone else who has stayed in situations."

Feb. 19, 2019: Another Scandal

Thompson was, once again, caught cheating on Kardashian when Hollywood Unlocked reported he was seen kissing Kardashian family friend Jordyn Woods at a house party in Los Angeles. Kardashian ended her relationship with Thompson for good as soon as she heard about the scandal.

March 2, 2019: Putting The Blame Where Blame Is Due

After facing criticism for initially blaming Woods for her split from Thompson, Kardashian addressed her breakup again in a series of tweets, placing the blame solely on Thompson.

"What’s been harder & more painful is being hurt by someone so close to me," she wrote. "Someone whom I love & treat like a little sister. But Jordyn is not to be blamed for the breakup of my family. This was Tristan’s fault. I have to move on with my life & count my blessings, my family, my health, & my beautiful baby True."

April 2019: Reunited

True to her word, Thompson and Kardashian put any bad blood behind them to celebrate True's 1st birthday together. The bash included a donut wall, pony rides, and, of course, photoshoots.

June 12, 2019: Coming To Her Own Defense

When Kardashian was accused of being the reason Thompson left his ex, Jordan Craig, while pregnant with their child, Prince, Kardashian insisted that, as far as she knew, Thompson was single when they started dating.

"He pleaded with me that the relationship was over long before we met," Kardashian wrote. "He had me talk with his most inner circle. He showed my physical proof (correspondence between the two) and had me on calls with his lawyers to prove his point. His best friends, business associates and even his mother told me, him and his ex were broken up before we met."

Kardashian did, however, acknowledge she was no longer sure if Thompson was 100% truthful about his prior relationship after everything that transpired between them, writing, "I really don't know what to believe."

Khloe Kardashian on Instagram

June 2019: Thompson Gives Kardashian an Extravagant Gift

In honor of Kardashian's 35th birthday, Thompson attempted to gift her a diamond ring. Footage of her reaction later played out on a December 2019 episode of KUWTK.

Kardashian had some reservations about accepting the gift. "'I go, 'I don't want a present from you... I really appreciate it. I don't think I can accept it,'" she explained to Scott Disick. "He's like, 'Just think about it. It's yours.' I go, 'Not everything needs to be bought.'"

March 2020: Quarantined & Single, Together

During the worldwide coronavirus pandemic, seemingly Kardashian and Thompson spent a lot of time together with True at Kardashian's home in Calabasas, California.

When a Twitter user speculated their living situation meant Thompson and Kardashian were back together romantically, Kardashian quickly cleared the air, writing, "he visits to see his daughter."

Kardashian later denied her family's speculation she and Thompson were "hooking up" while in quarantine. In a promo for the second half of KUWTK Season 18, Disick asked Kim Kardashian and Kris Jenner if they think the former couple has "slept together," but Kardashian immediately said no.

May 10, 2020: A Special Mother's Day

Thompson gifted Kardashian a super special Mother's Day balloon arch while she was quarantined at home in 2020.

Courtesy of Khloe Kardashian on Instagram
Elite Daily's It's Complicated

June 27, 2020: Tristan Says Khloé “Deserves The World” In Birthday Tribute

For Kardashian’s 36th birthday, Thompson posted a family selfie on the gram. In the caption, he called Kardashian a “beautiful and loving woman” and added, “You deserve the world Koko! True and I love you mama.”

July 1, 2020: Another Chance At Romance

A source for People revealed that Kardashian and Thompson were “giving their relationship another try.” They added, “Tristan is working hard to prove himself and has been a great dad to True.”

June 2021: Troé Calls It Quits Again

They reportedly called things off for good this time around. Kardashian had clearly reached her breaking point after all the allegations.

An insider told Entertainment Tonight that the couple “broken up recently” but nevertheless, “will continue to co-parent True together in a healthy, loving way.” It’s unclear exactly what day the couple split because at the time, the source noted that Kardashian and Thompson had “ended their relationship a few weeks ago.”

December, 2021: Tristan Fathered A Child With His Personal Trainer... While Dating Khloé

A paternity suit alleged that Thompson fathered a child with his personal trainer, Maralee Nichols in March 2021. (He was still dating Kardashian at the time.) The Daily Mail reported that Nichols was suing Thompson for child support. Yikes.

Court records published by The Daily Mail indicated that the baby was conceived during Thompson’s 30th birthday celebration in Nichols’ hometown, Houston. Nichols claimed their affair began five months before his birthday, but Thompson insisted it was a one-night-stand.

June 21,2022: Khloé Moves On With A Private Equity Investor

On June 21, Us Weekly reported that Kardashian was happily seeing a new mystery man — a private equity investor. And it was the result of some sisterly matchmaking at a dinner party, too. (Thank you, Kim!)

July 5, 2022: Tristan Is “Jealous” Of Her New Relationship

After everything he put her through, Thompson reportedly couldn’t handle his ex’s newfound happiness. A source told Us Weekly that Thompson “wants nothing more than to be back with Khloé, so of course, there’s jealousy there.” Hmm.

Meanwhile, Thompson was seen partying with a mystery woman at a night club in Las Vegas on July 3... so, yeah.

August 5, 2022: Welcome, Baby No. 2!

Kardashian and Thompson welcomed their second child via surrogate. On July 12, a representative for Kardashian told Elite Daily that their son was conceived via surrogate in November 2021. (Before Kardashian or the public was aware of Thompson’s paternity scandal with Maralee Nichols.)

A source told E! at the time that Tristan and Khloé “have not spoken outside of co-parenting matters.” Hoping these two can find a way to raise their little ones in peace.