Inside Rob Kardashian’s messy love life featuring six-year legal war with Blac Chyna & Twitter tirade against Rita Ora

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.

ADRIENNE BAILON

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."

ANGELA SIMMONS

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.

RITA ORA

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.”

RIHANNA

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.

BLAC CHYNA

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.

 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 : “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.