Love-Hate Relationships: Inside the Kardashians' and Jenners' Most Controversial Couplings
"Relationships can be tough, especially if the people close to you aren't supportive," says Khloé Kardashian
Anyone who’s been Keeping Up with the Kardashians (and Jenners) knows the famous family rarely stays mum when it comes to each other’s dating lives.
Khloé Kardashian shared her thoughts on introducing a new beau to the family on her website and app Friday, acknowledging, “Relationships can be tough, especially if the people close to you aren’t supportive.”
That said, in classic Khloé style, she added, “I don’t think you always have to listen to your parents’ or siblings’ advice, though!”
The youngest Kardashian sister, who is currently dating NBA player Tristan Thompson, reflected on how her family approaches new people entering their tight-knit group.
“I really do listen to my sisters,” she wrote, later adding, “I almost always already know what I’m doing but my sisters know that’s how I am. I’ll be honest and say that I don’t like the guy for the same reason. I’m self-aware and I’m often two steps ahead, so their advice doesn’t hurt me in any way.”
For Khloé, 32, it’s important to take some caution with a new relationship, writing, “I do think you have to really take heed if someone close to you doesn’t like the significant other — as long as it’s for valid reasons.”
And she would certainly know from experience as many of the KarJenners have weathered criticism about their romantic choices, both on screen and off, over the years.
Below, we look back at some of the family’s most controversial couplings.
Humphries’ boyish charm stole Kim’s heart, but his playfulness often caused rifts among family members. During a family vacation to Bora Bora, Humphries caused Kim to descend in to a fit of ugly crying after he infamously dragged her into the water and inadvertently caused her to lose an expensive diamond earring.
“What are you doing? Go away!” the matriarch yelled as Humphries splashed the women aboard the canoe.
“Robert, help me, Robert! I can’t see!” Jenner continued, begging for help after the canoe tipped. “Kim, talk to your boyfriend.”
After Humphries apologized, the momager asked, “What is wrong with you?”
In his confessional interview Humphries said, “I think it’s ridiculous that they’re all upset that their hair gets messed up, their makeup, this and that.”
Later on, Kris Jenner shared her sentiments about the ordeal — and Humphries.
“I don’t really know what to make of Kris Humphries, but if she’s in love, we all have to be patient and give Kris a chance,” she said.
The Kylie-Tyga-Chyna-Rob Quadrangle
And more recent dramatic romances have been those of Blac Chyna and Rob Kardashian, and Kylie Jenner and Tyga. First, Kylie and Tyga started popping up on each other’s social media accounts when the beauty mogul was just 17 and the rapper was 24.
And when Chyna and Rob went public with their relationship in January, fans were shocked to see the Kardashian brother coupling up with the woman who shares a son with his youngest sister’s boyfriend Tyga.
Chyna had also been entangled in a complicated, sometimes contentious, relationship with the reality star family, including going from Kim‘s BFF to an outsider of her circle. While on good terms, Chyna even attended Kardashian West’s wedding to Kanye West in 2014 — with Tyga as her date.
Soon after Rob shared the news, Khloé cryptically tweeted, “You can do anything. But never go against the family.”
Shortly after their engagement, Khloé continued to express her disdain in an episode of KUWTK.
When the Kardashian West comes to part of an article about the engagement that notes the famous family has yet to publicly comment on Rob’s news, Khloé whispered, “Why would we congratulate him?”
She then advised, “And no one should congratulate them, that’s so desperate and fake of whoever does first, because I know someone’s gonna break.”
Chyna was then accused by the Kardashians of manipulating her relationship with Rob, according to a source.
“No one [in his family] is jumping up and down with excitement today,” a source told PEOPLE of the Kardashian-Jenner clan after news of the engagement broke. “They have made a united decision as a family to not comment on social media yet about Rob’s engagement. The news is not shocking, and not totally unexpected.”
To make matters more dramatic, Chyna was allegedly ousted from an invite to a baby shower hosted by the Kardashian sister for Rob.
“Didn’t invite the Mother of my child to a baby shower you all were trying to throw for me ? You all must have lost your damn minds,” he wrote after sharing Kylie Jenner’s phone number on Twitter.
It seems as though everyone has reconciled, however, and Chyna and Rob welcomed their first child together, Dream Renée, earlier this month.
In an interview with PEOPLE in September, Chyna said there is no ill will between the couples.
“We’ve all talked, I’ve met up with Kylie,” said Chyna. “Everybody is mature. We’re not holding on to grudges. We’ve moved on.”
Oldest sister Kourtney might be once again living with the father of her three children, Scott Disick, but their partnership wasn’t always as evolved. In fact, Disick’s personal turmoil has had a considerable impact Kourtney and her family throughout the decade they’ve known each other.
Midway through their relationship — which is, as of now, focused on co-parenting rather than romance — Disick struggled to prioritize new fatherhood over his troubles with substance abuse. This created chaos as he unleashed a violent outburst in Miami, forced Kourtney to lock him out of their Hamptons home and cozied up to another woman in Monte Carlo, to name just a few low points.
Throughout Kourtney’s attempts to maintain her roller coast relationship with Disick over nine years, her family stood by her, occasionally having to live down rumors they were involved with Disick even as they couldn’t help but criticize Disick’s volatility and his “victim” mentality. And their help extended to little things, too, like helping her perfect her revenge body and taking her out for a sisters’ night out after the July 2015 split.
For now, the oldest Kardashian sister is heeding Khloé’s advice and remaining cautious when it comes to Disick. “She got screwed over by Scott so many times in the past,” a source recently told PEOPLE. “Kourtney is still protecting herself.”