The Saddest Things Khloé Has Said About Her Relationship With Tristan Thompson

No one does on-again, off-again quite like Khloé Kardashian and Tristan Thompson. From the multiple breakups to the subsequent reconciliations, the timeline of the couple's relationship is likely to give you whiplash. The "Keeping Up With the Kardashians" ("KUWTK") star and the NBA player, share a three-year-old daughter, True, and have had many ups and downs over the course of their five year history.

Kardashian and Thompson first got together in 2016 after getting set up on a blind dinner date by a mutual friend. By 2021, the couple called it quits for the third time, following what appears to be yet another instance of Thompson cheating on Kardashian. It can't be easy dating in the spotlight — let alone having your personal life documented and aired on national TV — but through the years, fans of the reality series have been able to follow along as Kardashian has navigated the bumps in her relationship with Thompson. Below we've rounded up the saddest things she has said about their relationship over the years. 

Khloé Kardashian breaks her silence on Tristan Thompson's first cheating scandal

On April 10, 2018, just two days before Khloé Kardashian gave birth to her daughter True, whom she shares with Tristan Thompson, TMZ released footage of Thompson allegedly cheating with two women months prior on October 7, 2017, when Kardashian was three months pregnant. The TMZ footage shows Thompson at a hookah lounge in Washington, D.C., where he was filmed kissing one woman and "motorboating" another woman, who also grabbed his crotch.

Understandably, Kardashian initially remained publicly silent, and chose to focus on her daughter in the wake of the scandal. Months later, however, while live-tweeting along with the episode of "KUWTK" in which she discovered Thompson's infidelity, she finally spoke out. On November 4, 2018, the reality star tweeted, "Oh well thank God a camera was NOT with me in Cleveland!!! I won't put in writing what I did but let's just say he's LUCKY I was9 (sic) months pregnant." We would have to agree that Thompson is lucky, because hell hath no fury like a woman scorned.

Tristan Thompson's infidelity was not about to ruin Khloé Kardashian's excitement about motherhood

On November 18, 2018, two weeks after her original response to the footage of Tristan Thompson's infidelity, Khloé Kardashian tweeted again. Said the former "Revenge Body" host, "I made it very clear that I was still disgusted by his actions but I wasn't going to let ANYTHING ruin this moment I've been waiting for my ENTIRE life#KUWTK."

Kardashian explained that while she was hurt by Thompson's actions — and no doubt hurt by being cheated on in the public eye — her main priority at the time was focusing on her daughter, True, and becoming a mother. The businesswoman certainly seems to love being a mom, calling True her "bestie" in an Instagram post and gushing that "It's so much more fun [to see the world through her eyes]" in an interview with ET. In the same interview, Kardashian reflected, "I think also motherhood just puts life into perspective and what's important to you," which explains her decision to devote herself to True rather than the cheating scandal fallout.

Khloé Kardashian has to deal with Tristan Thompson cheating again — with a friend of the family this time

Don't believe the myth — lightning actually can strike the same place twice, and that's certainly true for Khloé Kardashian and Tristan Thompson. At a party in February 2019, the NBA player was spotted cuddling up with Kardashian's sister Kylie Jenner's friend, Jordyn Woods. Woods was seen sitting on Thompson's lap, and the two "were all over each other, they were handsy, they made out," Kardashian later revealed in an episode of "KUWTK," according to Glamour. She somberly added, "I'll never understand the depths of his...ugh. I was just hoping for a better outcome for my daughter and myself."

Like the first time, this cheating incident led Thompson and Kardashian to split yet again, with the added sting of Thompson cheating with a friend of the family. After enduring a slew of tabloid coverage that detailed Thompson's second violation of her trust, The Good American founder tweeted in response, "This has been an awful week & I know everyone is sick of hearing about it all (as am I). I'm a rollercoaster of emotions & have said things I shouldn't have. Honestly, Tristan cheating on me & humiliating me, wasn't such a shock as the first time." Ugh, what a sad sentiment.

Heartbreak is a sad theme of Khloé Kardashian's life

Reflecting on the Jordyn Woods cheating scandal during a June 2019 episode of "KUWTK," Khloé Kardashian revealed how it was especially difficult to experience Tristan Thompson's infidelity, since she also faced intense scrutiny from the public and had television cameras recording her during some of her most intimate moments. Through tears, the businesswoman said (via US Weekly), "No one understands that I'm not just a TV show. Like, this is my life, and it, like, breaks my soul, and it's happened so many times." 

Indeed, it has happened "so many times." Sadly, the reality star has experienced the pain of being cheated on even before her tumultuous relationship with Thompson. In September 2009, Kardashian married now-former NBA player Lamar Odom just one month after they met, before separating in 2013 and finalizing their divorce in 2016. Odom revealed in a 2019 interview with People that he struggles with a sex addiction and cheated on Kardashian multiple times throughout their marriage. Kardashian had previously confirmed this sad truth to Howard Stern in 2016, telling the him, "It is humiliating on any level, but I found out he was cheating on me the majority of our marriage." Girl cannot catch a break!

Tristan Thompson's lavish apology gift put Khloé Kardashian in a 'conflicted' place

Are diamonds really a girl's best friend? On an episode of "KUWTK" that aired in December 2019, Khloé Kardashian received a diamond promise ring and a diamond necklace from Tristan Thompson, even though the two were broken up. Understandably, the reality star was conflicted about the bold gesture.

According to Buzzfeed, Kardashian said in the episode, "I am conflicted as to if I should keep it or not. I just really want to make sure there are no expectations. If I keep something, is that misleading? It's the sweetest, kindest gesture, but it doesn't mean a necklace is going to fix everything." She also reflected on the status of their bumpy relationship, saying, "Lately Tristan has been telling me he's sorry and that he loves and appreciates me. But right now, the most I can handle is co-parenting. I really believe that Tristan wants more than that but that's not what I'm about."

While it was a nice gesture, Thompson seemed to forget that money can't buy love.

Khloé Kardashian gave herself a sad premonition about her future with Tristan Thompson

To make matters even more awkward, on the same episode of "KUWTK" in which Khloé Kardashian received the lavish diamond gifts from Thompson, she FaceTimed him so she could say goodnight to True, who was staying with her father for the night. At the end of the call, Thompson said (via People), "All right, love you," to which the reality star responded, "Bye ... thank you." While he arguably deserved the cold response, all we can say is... ouch, that's got to hurt!

Kardashian's friends Malika Haqq and Khadijah Haqq McCray — who were there during this awkward exchange — were highly amused by Thompson's declaration. Kardashian responded, telling them that she didn't know what to say because she had no interest in reconciling with her ex-boyfriend. Said the Good American founder, "I just think now, I've already seen how this ride goes and I don't enjoy it. So it's like, why would I want to do it for a third time?"

You know what they say about famous last words, Khloé...

Khloé Kardashian wishes Tristan Thompson had never cheated

Khloé Kardashian definitely wishes that Tristan Thompson had been faithful to her (duh!). In December 2019, a fan tweeted to Kardashian, "I wished Tristan never messed up! Him and Khloé were so cute together! #KUWTK." The reality star succinctly (and savagely) responded to the tweet, writing, "Same babe. Same lol." Us too, Khloé!

Despite the clear shade toss, the reality star then went on to politely express her appreciation for at least one aspect of her relationship with Thompson."But we are coparenting so well right now," she wrote, adding, "It is a great space to be in. Coparenting is such a hard space. Much respect to all coparenters." Kardashian certainly has had several role models in this department — others in her family, including her older sister Kourtney Kardashian and Scott Disick; her parents, Kris and Caitlyn Jenner; and on-again, off-again couple Kylie Jenner and Travis Scott all co-parent their shared children.

Moving on from Tristan Thompson is hard for Khloé Kardashian

It can be hard to move on from your ex, especially after a tumultuous relationship with as many ups and downs as Khloé Kardashian and Tristan Thompson's had. According to US Weekly, on an episode of "KUWTK" that aired in April 2020, the reality star revealed to her mom, Kris Jenner, that several of her friends had been urging her to move on from Thompson and "hook up with someone" new. Then, the former "Kocktails with Khloé" host made the self-defeating admission that "I just don't care. I'm focused on myself and True and that's just what I do. Who knows? Maybe I'll never date again."

We certainly hope that isn't ... true (Get it?). Kardashian has rarely been single since she's been in the public eye. Before her marriage to Lamar Odom, she dated basketball player Rashad McCants. In 2014, she had an on-again, off-again relationship with French Montana, and in 2015, she dated NBA player James Harden. However, Kardashian has not dated anyone publicly since she and Thompson first got together. Maybe it's time for her to download Raya?

Even Khloé Kardashian didn't trust her second reconciliation with Tristan Thompson

It's all about trust. Per E!, the on-again, off-again couple reconciled yet again while quarantining for the COVID-19 pandemic, although it doesn't appear that the Boston Celtics player was able to earn back Khloé Kardashian's full confidence. On a September 2020 episode of "KUWTK," the businesswoman communicated her concerns about Tristan Thompson's fidelity and their rocky relationship history, according to Life & Style. She expressed to her beau that "One of my fears is you're acting like this until you get what you want, and if you do, you're gonna turn into like the old Tristan again."

She had already given him another chance after he first cheated on her in October 2017, so her doubts are more than understandable. Our hearts go out to her — this is a terrible way to feel in any relationship (especially one that has children involved), and it's extra sad since her worries eventually came true. Who knows, maybe Kardashian owns a crystal ball?

Khloe Kardashian once again sets herself up for disaster

You've got to go with your gut. On the second installment of the "KUWTK" reunion, which aired on June 20, 2021 but was filmed in April, host Andy Cohen asked Khloé Kardashian if she was able to trust Tristan Thompson after his several infidelities. The reality TV star responded earnestly, saying "I can't worry too much about everything else. I know the growth and all the work that he's done," seemingly referring to the past cheating allegations, according to Hollywood Life. She continued, telling Cohen, "I know the help he's got and the constant efforts that he makes every single day and how hard he fought to get back with me. You can ask everyone — it really wasn't an easy thing for him. But I don't understand why someone would go through all that if they weren't serious."

We don't understand why he would either, but Kardashian just may have jinxed her newly rekindled relationship by making that bold statement.

Once a cheater, always a cheater

Leopards don't change their spots, and cheaters rarely change their ways. Though Khloé Kardashian and Tristan Thompson did reconcile in the fall of 2020 while quarantining together with their daughter, the two broke up yet again following a new round of cheating allegations in June 2021.

According to E!, Thompson was spotted earlier in the month, hanging out with several girls on an upstairs deck at Nessel "Chubbs" Beezer's party in Bel-Air. He then reportedly whisked three women off to a private bedroom, returning to the party half an hour later with his clothes "disheveled," per the Daily Mail. One eyewitness even told E! that the athlete was telling other party guests that he was single. The audacity!

To make matters even worse, these new cheating rumors came out just one day after part two of the "KUWTK" special aired, when Kardashian had expressed her newfound trust in the NBA player. That has got to hurt. Just hours after the reports came out, news of the couple's split surfaced, so it seems that Kardashian is finally done giving him another chance.

Is True getting a younger sibling?

Will True Thompson become a big sister? In a February 2021 episode of "KUWTK," Khloé Kardashian expresses her hopes of having more kids with Tristan Thompson. In a conversation between the then couple, the Good American founder admits (via ET), "I don't know. True's getting older and I just feel like it's now time to have another kid." Thompson appears to agree, eagerly nodding and smiling, replying, "Yep. Mmmhmm. [That's what] I like to hear."

Thanks to the hindsight of knowing that Thompson would go on to cheat on Kardashian yet again after this conversation, seeing his enthusiasm at having another child with her is downright cringeworthy. Even sadder, Kardashian also told her beau that she was "ready to do the whole pregnancy thing again," and Thompson was all for it. Making this conversation especially heart-wrenching is the fact that the former "Revenge Body" host seems to adore being a mother and aunt, based on her frequent social media posts about her daughter, who is often pictured alongside her cousins. Luckily, Kardashian has frozen her eggs, so she has the option of having another child without Thompson if she so chooses.

Khloé Kardashian spends her 37th birthday in an unusually low-key way

On her 37th birthday on June 27, 2021, Khloé Kardashian responded to a tweet that inquired about her celebration plans and whether her fans were "going to get bomb a** birthday photos like last year." She replied, "I'm not doing anything today. I've just been swimming with True all morning. But we're having a great day," followed by several heart emojis. Khloé also tweeted that she spent her birthday "with my baby girl and then I ended the night in my pajamas, a glass of champagne and my beautiful family."

Kardashian and the rest of the Kar-Jenner family are known for their many lavish celebrations, from Kris Jenner's famous annual holiday party to North West's "Kid-chella" first birthday party, which featured a Ferris wheel, to Kim Kardashian and Kanye West's wedding celebration that spanned across multiple countries. So, a low-key birthday feels out of place for a Kardashian, which raises questions about how Khloé is doing emotionally and mentally in the wake of the breakup.