From Lamar Odom's Drama to Tristan Thompson's Infidelities: Khloé Kardashian's Complicated Relationship History

From seemingly endless divorce proceedings to her most recent drama, here's a look back at the star's relationship history through the years

01 of 18

TEENAGE TRYST

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Khloe Kardashian

Relationships come and go, but one thing's for sure about Khloé Kardashian: She's always been an open book — and like many of us, her first romantic experience wasn't actually all that romantic. "It's not funny to lose your virginity!" the reality star once wrote on her website, revealing that she first had sex at age 15. "It's weird and you're scared and it hurts and you don't know what will happen." Her male partner was older — and definitely not a virgin, she added. "I just wanted to get it over with. You definitely don't have an orgasm your first time. I didn't for the first few years!"

02 of 18

A WHIRLWIND ROMANCE

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JAKE HOLLY/startraksphoto.com

In August 2009, Kardashian met then-Los Angeles Lakers player Lamar Odom at a party. "I didn't even know who she was when I met her," Odom told Wendy Williams. "I went up and spoke to her, introduced myself. I fell in love. She's a beautiful person, inside and out." Within days, the two were joined at the hip. "They're very, very happy," Kardashian's sister Kim told PEOPLE at the time. "They're literally inseparable. Khloé thinks he's amazing, and he makes her laugh and smile constantly."

03 of 18

MAKING IT OFFICIAL

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JAKE HOLLY/startraksphoto.com

On Sept. 27, 2009 — one month to the day after they met, and nine days after getting engaged — 25-year-old Kardashian wed Odom at the Los Angeles mansion of music mogul Irving Azoff. The nuptials unfolded in front of the Keeping Up with the Kardashians cameras. "It may seem like a quickie wedding to everyone else, but Khloé knows what she wants," a source told PEOPLE at the time. "She and Lamar started talking about getting married really soon after they met. They knew this was it."

04 of 18

SWEET TIMES

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From the proposal onwards, Kardashian and Odom's relationship was heavily chronicled on the family's reality show, as well as for two seasons on the couple's own E! show, Khloé & Lamar — and it's safe to say the notoriously affectionate duo didn't hold anything back. After all, who could forget Kardashian's homemade "love tape" — candy bath, anyone?

05 of 18

THE BEGINNING OF THE END

Khloe Kardashian and Lamar Odom attend Lamar's daughter Destiny Odom's graduation in NYC
Splash News

In 2013, Kardashian and Odom's marriage began to show signs of serious train after the NBA star was hit with cheating accusations in July. A month later, he was arrested for driving under the influence, followed by a stint in rehab. After months of speculation about Odom's substance abuse issues, it was clear the marriage had fallen apart — and by December, Kardashian had filed for divorce.

06 of 18

'FRENCH' KISS

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Denise Truscello/WireImage

Just a few months after her emotional split from Odom, Kardashian began dating rapper French Montana in April 2014. The two rang in Kardashian's 30th birthday that summer, and were on-again, off-again until they officially split in December. The breakup was largely drama-free, with a source telling PEOPLE that Montana just "wasn't the perfect fit for her." There were no hard feelings, though, and they remained friendly.

07 of 18

HITTING ROCK BOTTOM

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On Oct. 13, 2015, Odom was rushed to the hospital after being found unconscious in a Nevada brothel. Kardashian immediately flew to his side, and he spent the following months recovering from a near-fatal overdose. As a result, Kardashian — who was making all of Odom's medical decisions — ultimately opted to call off their protracted divorce proceedings. Despite speculation that the two were reconciling, Kardashian insisted that wasn't their focus. "There are too many other important [medical] things [going on]," she told PEOPLE at the time. "It's not even in our brains thinking about us as a couple or having a relationship right now."

08 of 18

A HUSBAND ... & A BOYFRIEND

Khloe Kardashian and James Harden Celebrates Kylie Jenner 18th Birthday at Nice Guy
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As if she didn't already have enough on her plate, Kardashian juggled Odom's crisis with her budding relationship with Houston Rockets player James Harden, whom she'd been dating since summer 2015. By February 2016, the two had called it quits. (Kardashian later suggested he wasn't faithful.)

"When you break up in the public eye, it's almost like you have to go through it twice: privately and publicly," she admitted at the time. "It's humiliating. ... It's like pouring salt into an open wound. It definitely makes it hard to close that chapter of your life."

09 of 18

DIVORCE, ROUND TWO

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In February 2016, Odom made his first public appearance since his hospitalization, attending Kanye West's fashion show in New York City alongside Kardashian and the rest of her famous family — but soon enough, he appeared to have fallen back into his dangerous habits. In late May, Kardashian filed for divorce for a second time, and the proceedings were officially finalized that December.

"Khloé cares about Lamar," a source told PEOPLE of her decision to re-file. "But there's only so much you can do for a person. You can't help or fix someone who won't fix themselves."

10 of 18

MOVING ON

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With her failed marriage behind her, Kardashian turned her full focus to her new beau, Tristan Thompson, whom she began dating in September 2016. In the months that followed, Kardashian spent much of her time with the Cleveland Cavaliers player, regularly flying out to support him and even flaunting his NBA championship ring on social media. "She's very supportive of him, and they're getting serious," a source told PEOPLE in October 2016. "They really dig each other a lot."

There was a twist: At the time, the athlete was expecting his first child with ex Jordan Craig; she gave birth to a son that December.

11 of 18

BABY FEVER?

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Khloe Kardashian/Instagram

The romance took off from there — and Kardashian quickly made it clear she was ready for the next step, revealing on KUWTK in June 2017 that she had stopped taking birth control. "Tristan and I definitely talk about starting a family," she said. "He wants to have about five or six kids with me and that's lovely. We could start at one and we could grow from there." Later that month, a source told PEOPLE that Kardashian is "very happy and positive" about her future with Thompson. "She is absolutely hoping for an engagement," added the insider.

12 of 18

SHE'S EXPECTING

Khloe Kardashian And Tristan Thompson at LIV at Fontainebleau
Seth Browarnik/Startraks

In September 2017, multiple sources confirmed to PEOPLE that Kardashian and Thompson were expecting a baby together.

"They are absolutely thrilled," said one insider. "This is something Khloé has wanted for years and years and yet it's more than that: She didn’t want it unless she was in the right relationship for it."

"This is such a wonderful moment for her: not only is she going to be a mother, she is going to be raising a child with a man she truly loves," added the source. "Everyone is over the moon for them both."

13 of 18

THE ANNOUNCEMENT

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Khloe Kardashian/Instagram

At last! On Dec. 20, Kardashian finally confirmed the big baby news.

"Tristan, thank you for loving me the way that you do!" she gushed on Instagram alongside a photo of her and Thompson cradling her belly. "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! Thank you for making me so happy my love!"

14 of 18

TROUBLE IN PARADISE?

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With just days to go before Kardashian's due date, Thompson was seen speaking closely to a girl at a bar in Manhattan. Another video saw that same girl entering a hotel with Thompson at 5 a.m., prompting allegations that Thompson was cheating on Kardashian. “Tristan has been consistently cheating on Khloé,” a source told PEOPLE. “He’s a serial cheater. And there will be more women to come out of the woodwork.”

15 of 18

'TRUE' LOVE

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Khloe Kardashian/Instagram

She’s here! The reality star welcomed her first child, a baby girl named True, on April 12, 2018, days after the cheating allegations against Thompson surfaced.

“Khloé labored with [mom Kris Jenner] yesterday at the hospital. Tristan was there for the birth,” a Keeping Up with the Kardashians insider told PEOPLE. “He has practice today, but will spend as much time at the hospital as possible.”

“Everyone is focused on what’s best for their baby girl,” the source added. “Khloé is being the bigger person and letting Tristan bond with their baby.”

16 of 18

LOOKING UP

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Kourtney Kardashian/Instagram

The couple relocated to Los Angeles and spent the summer looking happier than ever as they rebuilt their relationship. "She is committed to keeping her family together," a source told PEOPLE. "And Tristan has shown that he is committed to Khloé, so Khloé will make it work.”

17 of 18

FALLING OUT?

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Tristan Thompson/Instagram

As fall began, though, Thompson moved back to Cleveland for his NBA season, while Kardashian and True stayed behind in Los Angeles. Sources told PEOPLE that their relationship was "up in the air," though they reunited to spend Halloween together as a family.

In the months that followed, the couple sparked multiple split rumors as Kardashian continued to post cryptic quotes on Twitter and Instagram, and Thompson seemingly remained out of the picture.

18 of 18

MAJOR BETRAYAL

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Mike Marsland/WireImage; Frazer Harrison/Getty; Phillip Faraone/WireImage

In February 2019, news broke that Thompson was allegedly once again unfaithful, this time kissing close Kardashian-Jenner family friend Jordyn Woods at a party.

“It’s amazing that she for so long was trying to keep her family together for True. It’s been very challenging for her,” a source told PEOPLE. “But in the end, now that they are 100 percent over, Khloé feels like she did everything she could to be in a relationship with Tristan. Clearly, he doesn’t care about his relationship with her.”

“She was deeply hurt by him and basically kept him at arm’s length,” a second source added. “The only reason she was still seeing him was because of True. The fact that her family is breaking apart is a nightmare for her, but it’s been a long time coming. They’ve been living separate lives.”

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