ROB Kardashian has had a messy love life over the years.
From the 34-year-old’s six-year legal war with ex Blac Chyna to his Twitter tirade with Rita Ora, take a look back at the reality star’s most dramatic moments in love.
Rob has been unlucky in love over the yearsCredit: Getty – Contributor
Some of his memorable relationships were with Chyna and Rita
One of Rob’s first high profile romances was with Cheetah Girls star Adrienne Bailon, 38.
The exes dated from 2007-2009, while their romance and split was heavily featured on Keeping Up With the Kardashians.
Rob confirmed they split after he cheated on her, though expressed his hopes to rekindle their romance.
During a 2016 episode of The Real, Adrienne admitted that Rob’s infidelity still impacted her years later.
She said: “I think anyone who has been in a relationship where they’ve been cheated on or hurt, it affects you.
“It affected me so much that I made it a conscious decision not to do that to the next person because when you experience the kind of hurt that being cheated on will make you question yourself.”
Rob cheated on Adrienne during their romanceCredit: Getty Images – Getty
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Following his split from Adrienne, Rob moved on with Angela Simmons, 34.
The KUWTK star’s fling with the Growing Up Hip Hop star only lasted for a few months in 2010.
However, the pair made many public appearances together as they attended Lakers games and were regularly spotted getting pedicures together.
Rob and Angela briefly dated in 2010Credit: Getty
One of Rob’s most tumultuous relationships was with Rita, 31.
The reality star and singer dated for two months in 2012.
While Rita previously said her short romance with Rob was “fun,” the pair famously feuded when Rob went on a Twitter tirade against his ex.
Rob accused Rita of cheating on him “with nearly 20 dudes” on Twitter, adding: “I wonder how many she’ll sleep with now that we apart? How can a woman who is so busy trying to start her own career have time to be with so many dudes all while in a relationship.”
Rob went on a Twitter tirade against RitaCredit: Getty
Following his split from Rita, Rob tried to move on with fellow singer Rihanna, 34, in August 2012.
Rob took Rihanna, who had just split from Chris Brown, on a first date that included go-karting day at Racer’s Edge Indoor Karting in Burbank, California.
They ended the night partying at the Los Angeles nightclub Playhouse.
Despite their fun first date, the romance fizzled and Rihanna rekindled her romance with Chris.
Rob went on a high profile date with RihannaCredit: Getty
Rob continued to casually date until he was linked with Chyna, 33, in January 2016.
The pair got engaged in April 2016, though split in December of that year after they had a number of intense fights.
The exes- who share five-year-old daughter Dream- have found themselves in the center of legal battles following their split.
Recently, Rob was suing Chyna with claims that she had attacked him with a six-foot metal pole about one month after their child was born.
He also alleged that she had tried to strangle him with an iPhone charging cord while intoxicated on cocaine and alcohol.
Trial was set to start in February 2021, but Rob dropped the lawsuit just days before it was supposed to begin.
Page Six revealed that the reality star motioned to “dismiss his assault lawsuit against Blac Chyna without prejudice for the sake of their daughter.”
According to the publication, a judge approved the motion and put an end to their nasty war over the assault allegations.
Days later, it was reported that Chyna is demanding her baby daddy pay her “substantial” legal bills after he dropped his assault lawsuit.
Her attorney, Lynne Ciani, recently told Radar: “In addition to dropping his lawsuit claiming over $750K in damages, Rob Kardashian must now pay for all of Chyna’s litigation costs.”
Via her lawyer, she also slammed Rob as a “bully” for seemingly trying to “intimidate and denigrate” her.
“Chyna is an excellent role model for women who want to stand up to former fiancés, or spouses, or boyfriends,” Lynne said.
The attorney added: “It is time for Chyna’s courageous and inspirational stand against Rob Kardashian, her powerful ex-fiancé, to be part of the public discourse.”
The 33-year-old model has been denying the allegations that she attacked Rob ever since he made the claims, and she was prepared to fight them in court.
Rob and Chyna have been battling it out in courtCredit: Getty – Contributor
The exes share daughter DreamCredit: krisjenner/Instagram
Following his tumultuous split from Chyna, Rob began a romance with Alexis Skyy, 27, in 2019.
The Love and Hip Hop alum defended their romance after Chyna’s then-boyfriend Kid Buu suggested Alexis was only interested in Rob because of his famous family.
According to PEOPLE, the rapper wrote on one of Alexis’ Instagram posts: “You really wit robs fat a** for love or is it just for clout?”
However, she defended their relationship by responding: “To answer your question…I love rob.”
Chyna also made numerous jabs at the reality star during her romance with Rob.
Despite insisting their love was real, Rob and Alexis eventually called it quits.
Alexis insisted she ‘loved’ Rob during their relationship in 2019Credit: Getty
KUWTK fans think Rob might dating Forma Pilates founder Liana Levi.
The romance speculation kicked off after the two signed a letter to a friend as a pair.
To celebrate their friend Nicolas Bijan welcoming a daughter, Rob and Liana sent flowers and a note.
The message read: “Roxy & Nicholas, Congratulations! So happy and excited for this next chapter in your lives. Can’t wait to meet your little princess.”
They ended the letter with: “Love, Liana & Rob.”
Not Skinny But Not Fat’s Amanda Hirsch first spotted it and wondered: “Wait, co-signing a card? Does Rob have a GF??”
Additionally, Rob re-shared Nicolas’ post of the note and said “we love you,” instead of just speaking for himself.
The NSBNT Instagram also pointed out that Rob and Liana seem to have known each other for years, with photos of them going back to 2012 of the pilate instructor’s page.
Liana appears to be a family friend, as Kendall Jenner, 26, regularly attended her pilates classes.
Fans think Rob is dating fitness instructor LianaCredit: Instagram/@lianalevi