Keenan Dayquan Ray Jackson—better known as YG—has been a fixture in the hip-hop scene for over a decade.

Rising out of Compton, YG built his reputation on streetwise lyrics and his affiliation with the Bloods, going from local hits with DJ Mustard to national stardom.

But while his music career has soared, his personal life has often been a chaotic “hot stankin’ mess”—and now, fans are worried that fellow California rapper Saweetie might not realize what she’s gotten herself into.

YG’s troubled history is well-documented. As a teenager, he spent his years running the streets and, at 18, was arrested for residential burglary.

After a short jail stint, he signed with Def Jam and released his debut album, *My Crazy Life*, in 2014. Since then, he’s dropped several more albums and collaborated with major artists. But drama has followed him offstage at every turn.

His romantic life is especially messy. In 2014, YG was dating Caitlyn Sparks, who even took a charge for him and spent time in jail. When asked if he was faithful to her during her sentence, YG dodged the question. Rumors soon circulated about him dating actress Keke Palmer, but he refused to confirm anything.

By the end of that year, Keke posted a video revealing she was heartbroken after finding out YG had gotten someone else pregnant. Around the same time, Caitlyn accused YG of giving her herpes and trying to pay her off—a claim she later retracted, saying her account was hacked.

YG’s daughter, Harmony, was born in 2015, with Caitlyn confirmed as the mother. Not long after, YG was shot in the hip while recording music, an incident that forced him to ramp up his personal security.

Despite the constant drama and danger, women continued to be drawn to him.

In 2019, YG went public with singer Kehlani. She later revealed that their relationship had actually been years in the making, overlapping with his involvement with both Keke and Caitlyn.

Their romance was turbulent—YG was caught kissing another woman just a month after going public. Kehlani brushed it off, saying they were in an open relationship, but later ended things after discovering infidelity through text messages.

She even released a song, “Valentine’s Day,” alluding to YG’s betrayal. Just months after their breakup, Caitlyn gave birth to YG’s second child.

YG’s reputation for cheating didn’t slow him down. He was briefly linked to influencer Brittany Renner in 2022. Meanwhile, Saweetie had her own high-profile breakup with Quavo in 2021, later being rumored to date several other celebrities.

In spring 2023, she and YG were spotted together, confirming their relationship with a vacation and public celebrations.

Fans have voiced concerns, pointing to YG’s track record of infidelity and drama. Many believe Saweetie is making a mistake, especially given the pattern of YG’s exes getting pregnant during his other relationships.

Despite the warnings, Saweetie has remained loyal, even attending an Usher concert without incident, which some fans praised as a sign of her commitment.

Whether Saweetie’s relationship with YG will beat the odds remains to be seen, but history suggests trouble may be ahead. For now, all anyone can do is wish them the best—and watch closely for what happens next.