It isn’t a secret that the Kardashian sisters have had their fair share of cheating boyfriends and failed relationships. However, Khloe has surprisingly been second in line after Kourtney and Scott Disick repeatedly take back a cheating man. The shock comes from 20 years of Khloe demanding her sister’s dumb losers and is quite closed off to men herself because of her lack of trust for “the male species.”

Us KUWTK fans can remember fond moments of Khloe slapping Scott, breaking into inboxes, and putting up thick walls, all for the prevention of anyone getting hurt. Khloe may have been on to something with Scott and Rashad McCants’s alleged cheating. Still, when she finally took down her walls to marry professional basketball player Lamar Odom, her deceivingly perfect relationship ended in more cheating, drugs, and devastation. Over the years, Khloe seemingly cannot catch a break with men; however, we might argue the past six years with NBA Tristan Thompson have been a mental and physical challenge for Khloe.

Bae, Bliss, and Baby

Back in 2016, the exciting possibility of Khloe having a new man was all the buzz. The magazines were thrilled about the news; however, Kris Jenner (who constantly nags Khloe about getting married) was surely over the moon about the spottings of Khloe with Tristan Thompson. Tristan Thompson of the Boston Celtics NBA team hit it off with Khloe, and the pair soon announced their relationship. The couple soon began posting their fairytale relationship through vacations, romantic holidays, and even couples Halloween costume that was, FIRE, am I right? The duo began making public appearances, and Tristan became a KUWTK cast member and part of the family. The whole family took a liking to him, seemingly fitting into the wildlife the family leads.

Khloe and Tristan state that they were in no rush for marriage but saw life and family together, and they got on that one quick. During the same time when the world was trying to be super sleuths and find out if younger sister Kylie Jenner was carrying a bun in the oven, Khloe’s news of her first and long-awaited pregnancy came out. In all the bae kisses and blissful experiences, the skeletons of Tristan’s nights away from Khloe made it apparent that he was cheating, and Khloe was enduring yet another unfaithful man.

It’s tough to say if the pair broke it off completely or just took a break after the incident, along with videos and photos to prove the allegations. Whether Khloe was still with Thompson or just supporting her child’s father, she was seen celebrating Thompson’s birthday and engaging with him at events. In that stage of life, could we really blame Khloe for trying to get things back to normal? after all, soon after, she delivered baby True Thompson into the world and finally found her true love.

More Drama and No More Baby Mama

In 2018 the couple was seen several times on what we would say to be “date nights” however, Khloe’s posts, constant solo flying at events, and more news about Tristan seeing other girls confirmed their separation. As Khloe dealt with the drama and press attention about her relationship, she enjoyed her life with True and her family by her side for support. The pair left us constantly wondering where their relationship stood with the spottings of them together and positive activity towards each other on social media.

The highly anticipated reconnection would be put on hold for even longer as one of the most shocking stories of 2019 came out for the world to see. Tristan was at it again, cheating and disrespecting the reality star, but this time with a friend of the family, Jordyn Woods. The devastating news came as a shock to the family who had loved and cared for Jordyn as their own, the ultimate betrayal from both Tristan and Jordyn.

As fully expected and appropriate, the Kardashian completely separated themselves from Jordyn and did what they could to separate from Tristan while still respecting him being Trues dad. Khloe and Tristan began co-parenting and working on their relationship while being weened out of the show more and more.

Compromise, Co-Parenting and Comes Backs

The situation’s sensitivity put massive pressure on the reality star, but as always, she removed the drama and pressed forward. Thompson worked over the next two years on himself, priorities, and daughter true. He is seen trying to get in Khloe’s good graces on both the show and social media, and we can’t say that hasn’t affected Khloe’s decision to give him a possible third chance.

Khloe expresses her lack of desire to date anyone and focuses only on her daughter, work, and family. Khloe thrived through her business in 2019 and truly became a role model for single moms. She focused on what she had to and removed anything irrelevant from her life; Khloe humbly allowed Thompson in her life for true and kept a civil friendship with him while they both worked on themselves and decided if their breakup was official forever.

More drama involving Kim, Kanye, and Tristan was shut down on KUWTK as Kim reminded everyone that Tristan is True’s dad and loved. The family has been clear about their reservations but truly wants what is best for Khloe and True. The couple exchanged heartwarming posts for each other’s birthdays and even considered another baby together. The news recently broke that the couple is seemingly back together officially and giving the relationship another try, hopefully for the long haul.