01of 18TEENAGE TRYSTKhloe KardashianRelationships come and go, but one thing’s for sure aboutKhloé Kardashian: She’s always been an open book — and like many of us, herfirst romantic experiencewasn’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!”

01of 18

TEENAGE TRYST

Khloe Kardashian

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Relationships come and go, but one thing’s for sure aboutKhloé Kardashian: She’s always been an open book — and like many of us, herfirst romantic experiencewasn’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!”

02of 18A WHIRLWIND ROMANCEJAKE HOLLY/startraksphoto.comIn August 2009, Kardashian met then-Los Angeles Lakers playerLamar Odomat a party. “I didn’t even know who she was when I met her,” Odomtold 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 sisterKimtold PEOPLE at the time. “They’re literally inseparable. Khloé thinks he’s amazing, and he makes her laugh and smile constantly.”

02of 18

A WHIRLWIND ROMANCE

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In August 2009, Kardashian met then-Los Angeles Lakers playerLamar Odomat a party. “I didn’t even know who she was when I met her,” Odomtold 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 sisterKimtold PEOPLE at the time. “They’re literally inseparable. Khloé thinks he’s amazing, and he makes her laugh and smile constantly.”

03of 18MAKING IT OFFICIALJAKE HOLLY/startraksphoto.comOn Sept. 27, 2009 — one month to the day after they met, and nine days after getting engaged — 25-year-old KardashianwedOdom at the Los Angeles mansion of music mogul Irving Azoff. The nuptials unfolded in front of theKeeping Up with the Kardashianscameras. “It may seem like a quickie wedding to everyone else, but Khloé knows what she wants,” a sourcetold PEOPLE at the time. “She and Lamar started talking about getting married really soon after they met. They knew this was it.”

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MAKING IT OFFICIAL

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

04of 18SWEET TIMESE!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?

04of 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?

05of 18

THE BEGINNING OF THE END

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Khloe Kardashian and Lamar Odom attend Lamar’s daughter Destiny Odom’s graduation in NYC

06of 18’FRENCH' KISSDenise Truscello/WireImageJust a few months after heremotional splitfrom Odom, Kardashian began dating rapperFrench Montanain April 2014. The two rang in Kardashian’s30th birthdaythat summer, and were on-again, off-again until they officiallysplitin December. The breakup was largely drama-free, with a sourcetelling PEOPLEthat Montana just “wasn’t the perfect fit for her.” There were no hard feelings, though, and theyremained friendly.

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‘FRENCH’ KISS

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Khloe Kardashian Celebrates Her 30th Birthday At TAO Las Vegas

Just a few months after heremotional splitfrom Odom, Kardashian began dating rapperFrench Montanain April 2014. The two rang in Kardashian’s30th birthdaythat summer, and were on-again, off-again until they officiallysplitin December. The breakup was largely drama-free, with a sourcetelling PEOPLEthat Montana just “wasn’t the perfect fit for her.” There were no hard feelings, though, and theyremained friendly.

07of 18HITTING ROCK BOTTOMDEBY/AKM-GSIOn Oct. 13, 2015, Odom was rushed to the hospital after being found unconscious in a Nevada brothel. Kardashianimmediately flew to his side, and he spent the following months recovering from a near-fatal overdose. As a result, Kardashian — who wasmaking all of Odom’s medical decisions— ultimately opted tocall 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],” shetold PEOPLEat the time. “It’s not even in our brains thinking about us as a couple or having a relationship right now.”

07of 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. Kardashianimmediately flew to his side, and he spent the following months recovering from a near-fatal overdose. As a result, Kardashian — who wasmaking all of Odom’s medical decisions— ultimately opted tocall 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],” shetold PEOPLEat the time. “It’s not even in our brains thinking about us as a couple or having a relationship right now.”

08of 18A HUSBAND … & A BOYFRIENDSplash NewsAs if she didn’t already have enough on her plate, KardashianjuggledOdom’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.”

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A HUSBAND … & A BOYFRIEND

Khloe Kardashian and James Harden Celebrates Kylie Jenner 18th Birthday at Nice Guy

As if she didn’t already have enough on her plate, KardashianjuggledOdom’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.”

09of 18DIVORCE, ROUND TWOKevin Mazur/GettyIn February 2016, Odom made his first public appearance since his hospitalization, attendingKanye West’s fashion show in New York Cityalongside Kardashianand the rest of her famous family — but soon enough, he appeared to havefallen back into his dangerous habits.In late May, Kardashianfiled for divorcefor 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.”

09of 18

DIVORCE, ROUND TWO

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In February 2016, Odom made his first public appearance since his hospitalization, attendingKanye West’s fashion show in New York Cityalongside Kardashianand the rest of her famous family — but soon enough, he appeared to havefallen back into his dangerous habits.In late May, Kardashianfiled for divorcefor 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.”

10of 18MOVING ONSplashWith her failed marriage behind her, Kardashian turned her full focus to her new beau,Tristan Thompson, whom she begandatingin 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 sourcetold PEOPLEin 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.

10of 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 begandatingin 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 sourcetold PEOPLEin 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.

11of 18BABY FEVER?Khloe Kardashian/InstagramThe romance took off from there — and Kardashian quickly made it clear she was ready for the next step, revealing onKUWTKin June 2017 thatshe 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 sourcetold PEOPLEthat Kardashian is “very happy and positive” about her future with Thompson. “She is absolutely hoping for an engagement,” added the insider.

11of 18

BABY FEVER?

Khloe Kardashian/Instagram

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The romance took off from there — and Kardashian quickly made it clear she was ready for the next step, revealing onKUWTKin June 2017 thatshe 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 sourcetold PEOPLEthat Kardashian is “very happy and positive” about her future with Thompson. “She is absolutely hoping for an engagement,” added the insider.

12of 18

SHE’S EXPECTING

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Khloe Kardashian And Tristan Thompson at LIV at Fontainebleau

“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 wasin the right relationshipfor 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 witha man she truly loves,” added the source. “Everyone is over the moon for them both.”

13of 18

THE ANNOUNCEMENT

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“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!”

14of 18TROUBLE IN PARADISE?Jackson Lee/Splash NewsWith 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.”

14of 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.”

15of 18

‘TRUE’ LOVE

True Thompson.Khloe Kardashian/Instagram

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“Khloé labored with [momKris Jenner] yesterday at the hospital. Tristan was there for the birth,” aKeeping Up with the Kardashiansinsider told PEOPLE. “He has practice today, but will spend as much time at the hospital as possible.”

16of 18LOOKING UPKhloé Kardashian and Tristan Thompson.Kourtney Kardashian/InstagramThe couple relocated to Los Angeles and spent the summer looking happier than ever as they rebuilt their relationship. “She is committed tokeeping her family together,” a source told PEOPLE. “And Tristan has shown that he is committed to Khloé, so Khloé will make it work.”

16of 18

LOOKING UP

Khloé Kardashian and Tristan Thompson.Kourtney Kardashian/Instagram

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

17of 18FALLING OUT?Tristan Thompson/InstagramAs fall began, though, Thompson moved back to Cleveland for his NBA season, while Kardashian and Truestayed behindin Los Angeles. Sources told PEOPLE that their relationship was “up in the air,” though they reunited tospend Halloween togetheras a family.In the months that followed, the couple sparked multiple split rumors asKardashian continued to post cryptic quoteson Twitter and Instagram, and Thompson seemingly remained out of the picture.

17of 18

FALLING OUT?

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As fall began, though, Thompson moved back to Cleveland for his NBA season, while Kardashian and Truestayed behindin Los Angeles. Sources told PEOPLE that their relationship was “up in the air,” though they reunited tospend Halloween togetheras a family.

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

18of 18

MAJOR BETRAYAL

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

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In February 2019, news broke that Thompson was allegedly once again unfaithful, this time kissing closeKardashian-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.”

source: people.com