The reality TV star and NBA player dated back in 2015 after she announced she'd split from her ex-hsuband of seven years, Lamar Odom. Less than two months after going public with their romance, they called it quits, with James later admitting he grew tired of constantly being hounded by the paparazzi following Khloe.
"I didn't like all the attention. I feel like it was for no reason," he later told Sports Illustrated of the "worst year" of his life.
"I wasn't getting anything out of it except my name out there and my face out there, and I don't need that— it wasn't uncomfortable, but it wasn't me."
He continued: "I don't need pictures of myself when I'm driving my car. Who cares? What shoes am I wearing? Who cares? Where am I eating? Who cares?"
Jordyn's dalliance with James comes weeks after her relationship with Kylie was called into question. Although it's been months since she and Tristan Thompson made headlines for their infamous hookup, the Kylie Cosmetics founder said in the latest teaser trailer for the upcoming season of KUWTK that she's still struggling to come to terms with losing her best friend of nearly a decade.
"So, Jordyn - do you miss her? Do you want to be friends with her?" Khloe asked Kylie as they discussed the scandal's after-effects.
"I think this whole Jordyn situation needed to happen for a reason - for me, for her, for you, for everybody," the 21-year-old mum to Stormi Webster, 1, replied carefully. "She was my security blanket, she lived with me. We did everything together."
The makeup mogul continued: "I just felt like I have Jordyn, I don't need anything else. And I feel like there's a part of me that needed to grow without her. Sometimes people are there for certain reasons at certain times in your life, and then not there for others."
Khloe— who shares daughter True Thompson with her former NBA player boyfriend— went on to praise Kylie for her mature attitude towards the situation.
"I really respect in you that you're really good at being calm even when you probably do wanna scream at someone. I think it's because you're so confident and secure with who you are, which is so wonderful.
"It's a really inspiring trait that you have, Khloe gushed.
"I feel like we're all just so lucky to have each other. I feel a lot of the reason I am the way I am is because of you guys," Kylie said, referencing the famously close bond between the Kardashian-Jenner sisters Kourtney, Khloe and Kim Kardashian and Kylie and her supermodel sister Kendall Jenner.
Their candid conversation follows news that after some much-needed healing time, Jordyn and her billionaire ex-bestie are reportedly trying to get their decade-long friendship back on track.
An insider recently dished to Us Weekly that the pair are not only on speaking terms but are working tirelessly to move on from Jordyn's inappropriate and deceitful behaviour.
"Their relationship is on the road to recovering," a source close to the pair said.
While forgiving Jordyn and welcoming her back into life with open arms is a brave move on Kylie's behalf, the insider said we won't be seeing the former besties together in public anytime soon. Why? Because they're nowhere near as close as they were before she made headlines for all the wrong reasons.
"Kylie knows the separation from Jordyn will help both of them—and Kylie’s family—to heal," the Us source said.
While their reconciliation may come as a shock to some, eagle-eyed fans predicted the pair were working through their differences months ago when Kylie and Jordyn were spotted having lunch at a restaurant.
Jordyn isn't the only celebrity trying to get back on the family's good side! According to The Sun, Tristan is desperately trying to win Khloe back. And she's reportedly "torn" as to whether she should allow him back into her life.
"Khloé is totally confused – Tristan has been begging her to get back together, and he posted that long gushing birthday message to her too," the source told the outlet. "He’s been asking her to sit down with him properly, have a heart to heart – but she’s refusing."
The source continued: "She wants to keep things civil for True’s sake, but she doesn’t want to risk falling for him again and getting her heart broken all over again."
WATCH: TRISTAN SAID HE TRIED TO KILL HIMSELF AFTER KHLOE DUMPED HIM
Earlier this month, the shamed NBA basketballer shocked the world when he posted a photo of Khloe and True to Instagram on her 35th birthday, thanking the mother of his child for being "an amazing mommy" and a "beautiful human".
"Happy birthday @khloekardashian,” he captioned a photo of the Good American founder with their 14-month-old daughter True. “You are the most beautiful human I have ever met inside and out,” he continued. “Thank you for being an amazing mommy to our princess True. She is blessed to have someone like you to look up to. I wish you nothing but more success and sending you positive blessing your way. Enjoy your day Koko.”
The post— which was Tristan's first public address to the reality TV star since the cheating scandal broke— had fans convinced he was trying to win Khloe back. More fuel was added to that fire when news surfaced that he had purchased a house close to where the A-lister and their daughter lives. According to the Mirror, he moved closer to the pair to "prove his loyalty" and try win her back.
"He’s really keen to show her he’s changed, though – he’s even buying a big ‘family’ house near Khloé's LA home so he can have True to stay more often, and saying he’d do anything to put things right. Khloé's torn," the insider also told The Sun.