Kanye West and Irina Shayk have sparked romance rumors after being spotted in France together on a vacation. This is the first time West has been single after being married to Kim Kardashian for seven years. The relationship has apparently been going on for quite a few months but that’s all that fans know so far. That being said, the A-list women West dates now is different from some of the baddies he was linked to back in the day. Here are some of the women who West was once linked to.

Kanye West debuted his relationship with exotic dancer turned model Amber Rose in 2008. The rapper was riding high off the great success of his collab-heavy album, Graduation. The couple eventually broke up in 2010. While their relationship seemed like it lasted more than a mere two years, that was probably because they were so heavily featured in the media for Amber’s unusual look and the couple’s antics together. Ultimately, Amber blamed their breakup on West being more interested in future wife Kardashian and even calling her a “homewrecker” in an interview. West, on the other hand, shared that his album My Beautiful Dark Twisted Fantasy was heavily inspired by their relationship. Uh, have you heard the album?

Alexis Phifer began dating the rapper from 2002 to 2004 and then getting back together in 2006 that resulted in an engagement. Unfortunately, the couple broke off their engagement in 2008 with Phifer pointing to West’s life on the road causing problems for the young couple. It is also important to note that the ending of the engagement was close to the passing of West’s mother Donda West, which fans know still affects the rapper to this day.

The model was linked to West all throughout 2010, but the couple never actually confirmed if they were an exclusive item. Selita Ebanks appeared on the red carpet of several events with the musician. West was a Grammy winner at this time, and becoming known for his shocking outbursts. The model also appeared in the music video for his single Runaway. Fans speculated that the relationship was a publicity stunt or maybe just a “close friendship” since she appeared in his music video around the same time.

Lucky girl Brooke Crittendon is a lesser-known girlfriend but at the time, she was an assistant at MTV where she most likely met West. This relationship started sometime in 2005 and became cemented in stone in 2006 when the aspiring actress accompanied West and his mother to the Grammys in February of that year. Things clearly did not end well for the former couple because Crittendon has since called the rapper a “big baby”, “not macho”, and “insecure”. She also claims their relationship ended because of all the attention he gave to other women.

The rapper is said to be “content” with Shayk currently which makes sense because the couple’s friendship is not new, they have worked together in the past. The mom of one appeared in West’s music video for Power and she also walked in his Paris fashion show a few years after that. So, they have definitely crossed paths in the past. He clearly thought she was attractive because he gave her a shout-out in his song Christian Dior Denim Flow way back in 2010. The couple’s relationship is unfolding for the world to see.