Halle Bailey and Boyfriend DDG’s Relationship Timeline

Actress Halle Bailey and Darryl Dwayne “DDG” Grandberry Jr. first met through their respective careers.

“I’ve been a fan of his for years,” the Little Mermaid actress gushed to Essence in November 2022 of her rapper beau. “I grew up being on YouTube and would always see the young Black creators and was constantly inspired by them. He was one of them.”

While Bailey — who rose to fame as a young singer alongside her sister Chloe Bailey — first stumbled across DDG’s videos in 2015, she soon “forgot about him.” She added to the outlet: “But then I saw that he was dropping music, and I really gravitated toward this one song. Coincidentally he messaged me — and the rest is history.”

The Grown-ish alum and the “Moonwalking in Calabasas” performer first sparked dating speculation in January 2022 when they were spotted together at Usher’s Las Vegas residency. Nearly two months later, DDG made their romance Instagram official.

“Happy Birthday to the beautifulest, the flyest, the sweetest ❤️ love you forever 🥺💎,” he wrote at the time, sharing a since-deleted video of Halle.

The Grammy nominee and DDG later made their red carpet debut as a couple that June when they stepped out at the BET Awards.

“I have my boo with me today,” Helle exclaimed to Extra correspondent Rachel Lindsay on the red carpet. “We’re so excited. We’re gonna have so much fun just supporting Chloe [for her solo performance]. It’ll be great!”

She added at the time: “I was so nervous, like, were trying to figure out what to wear [and] all this stuff.”

Amid the pair’s whirlwind romance, they also faced cheating allegations. DDG was accused of cheating on Halle with his ex-girlfriend Rubi Rose in February 2023 after Rose claimed he had gifted Halle one of her old shirts. Both the “Hood Melody” rapper and the Georgia native have since shut down the claims.

“The devil is working lol,” Halle tweeted at the time, denying the allegations. “Please don’t feel into the lies, especially from a third party. Stay blessed everyone.”

While Halle and DDG have since kept their romance to themselves, the Color Purple actress offered rare insight into their “deeply sacred” bond in April 2023.

“There’s a lot of eyes on me now, especially with what’s to come. And sometimes I wish I didn’t have so many eyes on me, especially experiencing something like this for the first time,” Halle told British Vogue of falling in love with DDG.

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Scroll below to see Halle and DDG’s complete relationship timeline: