Inside Kanye West's Troubled Dating History — Including his 'Unhappy' Marriage to Bianca Censori and 'Toxic' Divorce with Ex-Wife Kim Kardashian

Kanye West's first known romance before he became one of the most sought-after rappers in the industry was with his high school sweetheart, Sumeke Rainey. Their relationship inspired his track Never Let Me Down from his debut album, The College Dropout, released in 2004.

They soon broke up as West chased the spotlight in the 1990s.

The Yeezy founder eventually moved on with Alexis Phifer and dated her between 2002 and 2008.

They broke up in 2004 but reconnected a year later. He then proposed to her in 2006, though they ended up calling off their engagement and splitting for good in 2008 months after the death of West's mother, Donda West, due to plastic surgery complications.

After their fallout, Phifer reflected on their relationship in her interview with People.

"It's always sad when things like this end, and we remain friends," she said. "I wish him the best in his future and all of his endeavors. He's one of the most talented people I've ever met."

After his first breakup with Phifer, the hitmaker dated Harlem Heights actress Brooke Crittendon. They split but remained amicable afterward.

"[I] had to live in the shadow of that's 'Kanye's ex-girl.' I'm so much bigger than that," she told Essence regarding the spotlight she received as Kanye's former muse.

West moved on with Amber Rose and dated her for two years from 2008 to 2010, but they called it quits after he reportedly cheated on her with Kim Kardashian. Their breakup left a bitter taste in their mouths, though it helped the rapper create his album My Beautiful Dark Twisted Fantasy.

Speaking about the album and their relationship, Rose said: "It's a great part of history, and it's a great part of hip-hop, and I'm happy to be a part of it, but that time was not a great time for me."

"I'm famous, and I'm broke. I can't date anyone else. I can't say anything on the Internet because Kanye has such a voice. If I was going to kill myself, I would have done it during those times," she added.

West was linked to Selita Ebanks in 2010. They made public appearances together for months, but the dating rumors died down afterward.

West and Kardashian's friendship blossomed after the latter's infamous 72-day marriage to Kris Humphries.

Following his proposal at AT&T Park, they tied the knot in Florence, Italy, in 2014. They share four kids together: North, Saint, Chicago and Psalm.

Their turbulent marriage ended for good when the Keeping Up With the Kardashians alum filed for divorce on February 19, 2021.

Shortly after his split from Kardashian, West sparked dating rumors with Irina Shayk. The buzz intensified after the public spotted them celebrating his 44th birthday in June 2021.

Per sources, they briefly dated before breaking up in August 2021.

West began his whirlwind romance with Julia Fox in January 2022 while processing his divorce from Kardashian. Their relationship did not last long, but a representative said they remained friends and collaborators after the split.

Fox soon told ES magazine that West's unresolved issues led to their breakup.

"It just seems like he had a lot to work on, and I just don't have time for it or energy. I don't have the bandwidth or emotional capacity for it," she continued.

As soon as West and Fox called it quits, the Gold Digger hitmaker was seen shopping with model Chaney Jones in February 2022. They seemingly confirmed their relationship through social media interactions, but their romance ended as quickly as it started.

West married Yeezy designer Bianca Censori in a private ceremony in California on December 20, 2022. He seemingly hinted at their connection in his song Censori Overload while making public appearances together.

The entertainer has received plenty of backlash for his behavior toward Censori, with critics claiming she's "unhappy".