Ladies Love Sosa! Breaking Down Rapper Chief Keef's Storied Dating History

Since 2012, Chief Keef has been a major player in the hip-hop industry. His debut single, "I Don't Like,” catapulted him into the spotlight, and he hasn’t slowed down since.

While his music career has been at the forefront of his public image, Keef’s dating history has also garnered attention. The rapper, known for his controversial and outspoken persona, has been in relationships that were just as publicized as his music career.

One of Chief Keef’s most notable relationships was with the reality TV star Slim Danger – with whom he shares a son. Their relationship was highly publicized, with Slim Danger frequently appearing in the media to discuss their dynamic and co-parenting experiences. Slim previously appeared on the now canceled Thots Next Door and revealed that she was intent on getting pregnant by the rapper.

“I didn’t get pregnant yet, so I was like, ‘I gotta do a little bit more manifestation. I got to get pregnant,'” Slim said (via Heavy), adding, “I told him. I was like, ‘Yeah, I’m pregnant,’ and he said, ‘Join the crew.'”

Keef also dated several other women in the entertainment industry. Fans closely followed his relationship with Pretty Mesha, a model and social media influencer. Their on-again, off-again status kept followers guessing about the true nature of their relationship. In 2021, Media Take Out reported that Keef and Mesha were engaged, per Hot New HipHop. However, the two never made it down the aisle, and Keef has since moved on to a new relationship.

Chief Keef has stayed lowkey when it comes to his dating life, but that has not stopped fans from linking him with other celebrities. In June, rumors about Keef’s friendship with Sexyy Red came into question after the two posted a series of flirty images on social media. Fans and celebrities alike took to the comment section to inquire about the true state of their relationship.

“This why n---as don’t believe us when we say n---as the bro,” rapper JT wrote.

A fan added: “This the dread head she been singing bout, 'Bae I love you, you my everything.'”

Keef and Sexyy have since shot down rumors that they are dating, instead suggesting that they are just friends.

Speculation about their relationship was exacerbated after Sexyy suggested Keef cheated on her with King Von’s sister, Kayla B. Meanwhile, Kayla has declared that she is Keef’s main girlfriend.

She took to social media to share a snap of her and the “Love Sosa” rapper – pairing the image with Sexyy’s song “U My Everything.” Sexyy responded by posting a photo of Keef that she took while they were together, but Kayla did not seem too bothered, commenting, “Damn, he didn’t even change the outfit.”

It's unclear if Kayla and Keef’s relationship is genuine, but fans refuse to believe that Sosa is dating Sexyy. The two have a collaboration in the works, leaving some to believe their interactions are staged.