Kanye West’s love life has been one wild ride. From high school sweethearts to brief flings with models, the rapper has had very messy breakups. His whirlwind romance with Amber Rose and his tumultuous marriage with SKIMS mogul and ex-wife Kim Kardashian have kept his love life in the spotlight. His recent trysts with Bianca Censori, whom many have called Kardashian’s lookalike, also continued to fuel Tinseltown gossip mills and social media chatter. Here is a look at his interesting romantic past.

1. His Early Romances

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Before Ye became a global icon, he dated his high school sweetheart, Sumeke Rainey. He referenced her in his song Never Let Me Down: “Nothing sad as that day my girl’s father passed away/ So I promised to Mr. Rainey I’m gonna marry your daughter.” However, their romance ended as Ye rose to stardom. The rapper then dated designer Alexis Phifer on and off from 2002 to 2008. Their relationship hit a rough patch when Ye’s career skyrocketed after The College Dropout’s release in 2004. They later reunited, and Ye proposed in 2006 during a Capri vacation. Sadly, after an 18-month engagement and Donda West’s tragic passing, they called it quits in 2008. Briefly, Ye also dated Brooke Crittendon, a former MTV employee; she attended the 2006 Grammys with him and his mother.

2. Amber Rose

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Ye’s love life has been a rollercoaster ride, to say the least. His relationship with Amber Rose made headlines when she claimed he bullied her after their 2010 split. She stated, “The only thing I got from him was fame,” according to Fox News. The My Beautiful Dark Twisted Fantasy album was inspired by their breakup. Rose didn’t mince words and shared, “That was not a great time for me.” Subsequently, she went on to marry Wiz Khalifa, and the pair had a kid together before eventually getting a divorce.

3. Kim Kardashian

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West married Kardashian in 2012 after she called quits on her marriage with Kris Humphries. Ye and Kardashian were close acquaintances for years, running into each other at fashion events. Soon, however, the couple was expecting little North. Ye pulled off an over-the-top proposal at AT&T Park, and the both of them eventually tied the knot in 2014. The duo then became proud parents to Saint, Chicago, and Psalm. However, their relationship was filled with drama as Ye continued to rant about private familial issues on social media. Kardashian eventually filed for divorce in 2021 and dated Pete Davidson, who engaged in public feuds with the rapper.

4. Ye’s Post-Kim Flings

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After Kardashian filed for divorce, Ye was spotted in France for his 44th birthday with model Irina Shayk, who shares a kid with Bradley Cooper. An insider shared that, “She seems smitten.” They weren’t officially dating, but it seemed as though there were mutual interests. Then, around New Year’s 2022, West was dating actress Julia Fox, only for their whirlwind romance to be over by Valentine’s Day. Fox later claimed that Ye had ‘unresolved issues’ for which she didn’t have the ‘bandwidth.’ West then dated model Chaney Jones for five months thereafter, until they split in June 2022 after a Japan trip, as per People.

5. Bianca Censori

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After splitting up with Jones, Ye started seeing Censori, who worked for his Yeezy brand as an architect. In late 2022, he named a song after her, Censori Overload. They were spotted on a romantic dinner date in Beverly Hills in early 2023. Rumors then swirled that they secretly tied the knot, though it remains murky whether the marriage was legally binding, as per Yahoo! Entertainment. Fast forward to the present, Kanye and Censori seem happy together, with the rapper taking a particular interest in dressing her up. The duo is known for their controversial and risque outfits as they trot across the globe.