A Timeline of Kanye West's Dating History

On the heels of his divorce from Kim Kardashian following six years of marriage, PEOPLE confirmed on June 9, 2021, that the rapper is seeing model Irina Shayk. 

Here, we look back at West's past relationships, from his high school sweetheart and his first fiancée to his marriage to the Keeping Up with the Kardashians star and his new flame. 

Before he became a household name, West was dating his high school sweetheart. While their relationship remained out of the public eye, he referenced her on "Never Let Me Down," a track on The College Dropout. 

"Nothing sad as that day my girl's father passed away / So I promised to Mr. Rainey I'm gonna marry your daughter," he rapped in the song. The pair's relationship ended as he rose to stardom. 

The rapper and designer dated on and off from 2002 until 2008. The pair went through a rough patch when West's career skyrocketed in 2004 after the release of his album The College Dropout. They later reunited and in August 2006, the Grammy winner proposed to Phifer over a lobster and pasta dinner while vacationing on the island of Capri. 

After an 18-month-long engagement, during which West's mom Donda unexpectedly died, the pair called it off in early 2008.

"It's always sad when things like this end, and we remain friends," Phifer told PEOPLE at the time. "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."

The former MTV employee and Harlem Heights star dated the actor during a brief split from Phifer, and attended the 2006 Grammy Awards with him and his mother before splitting from him that summer. 

Crittendon later spoke to Essence about the pressure the spotlight on the relationship put on her, saying in 2009, "[I] had to live in the shadow of that's 'Kanye's ex-girl.' I'm so much bigger than that." 

She added that the relationship ended on good terms. "Mr. West and I are amicable. I wish him the best and he wishes me likewise. As far as I'm concerned if he ever needed anything I'd be there and [he would do] the same for me."

The "Fade" rapper dated the model from 2008 until 2010, following his split from Phifer. Rose called it off, and later alleged that she endured "constant bullying" from the rapper in the wake of their split. 

"The only thing I got from him was fame. I had to just take that," Rose said in a 2017 interview with Complex's "Everyday Struggle" talk show. "I had to take that heartbreak on top of it."

Opening up about West's Grammy-winning album My Beautiful Dark Twisted Fantasy, which was inspired by their breakup, she 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." She continued, "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."

Rose went on to marry rapper Wiz Khalifa in 2013, and shares son Sebastian Taylor with him. After the pair divorced, she began dating music executive Alexander "AE" Edwards, and welcomed son Slash Electric with him in October 2019.

After ending her 72-day marriage to Kris Humphries in 2012, Kardashian began dating the rapper, with whom she had a longstanding friendship.

By December of that year, the pair announced that they were expecting their first child together. Four months after welcoming daughter North in June 2013, West popped the question in an elaborate proposal at San Francisco's AT&T Park.

The pair wed in 2014 in Florence, Italy. The musician and reality star went on to welcome son Saint in December 2015, before later expanding their family with daughter Chicago and son Psalm via surrogate in 2018 and 2019, respectively.

Kardashian and West have gone through a rollercoaster of public ups and downs throughout their relationship, and Kim ultimately filed for divorce on Feb. 19, 2021.  

Several months after Kim filed for divorce, PEOPLE confirmed on June 9 that West is seeing model Irina Shayk, who shares a daughter with ex Bradley Cooper.

The pair were spotted in France together, where West celebrated his 44th birthday. 

"She seems smitten," a source told PEOPLE of the new item. "He invited her to France and she happily accepted. They are not officially dating but there is an interest from both sides."

"They have known each other professionally for years. He started pursuing her a few weeks ago. Kanye is a persuasive guy," the source added, noting, "He hung out with her in N.Y.C. before they celebrated his birthday in France."

Shayk previously modeled for Yeezy and appeared in his 2010 music video for "Power."

Another source told PEOPLE that Kim has been aware of the budding romance "for weeks." 

"It doesn't bother Kim that Kanye is dating," the insider said. "Her only concern is their kids. She wants Kanye to be present and spend as much time with them as possible. The kids love when Kanye is around."