Actress Halle Bailey and rapper Darryl Dwayne “DDG” Grandberry Jr. first met through their respective careers.
“I’ve been a fan of his for years,” the Little Mermaid star gushed to Essence in November 2022. “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 Halle — 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: “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.”
Halle and DDG first sparked dating rumors in January 2022, two months before going Instagram official. The next year, Halle revealed that they have a “deeply sacred” bond.
“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 in April 2023.
In October 2024, DDG announced that he and Halle split less than one year after welcoming their son, Halo.
Scroll below to see Halle and DDG’s complete relationship timeline:
January 2022
The duo were first spotted together at Usher’s Las Vegas concert.
March 2022
“Singing lessons with @DDG,” the Lion King actress captioned a TikTok video with her man as they completed vocal warm-ups.
June 2022
Halle and the “Impatient” artist twinned in black at the BET Awards, which marked their first joint red carpet appearance.
February 2023
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 DDG and Halley 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.”
Weeks later, they fueled breakup speculation when DDG tweeted “All these girls the same, ain’t no way.” They also noted that the rapper unfollowed the actress. Halle’s older sister Ski Bailey then chimed in via Instagram Live, theorizing that DDG could have cheated on her sibling since he and Rose frequently accused one another of infidelity prior to their 2020 split.
“Nobody cheated on nobody btw. Don’t take my tweets too serious [sic],” DDG tweeted at the time, swiftly denying the claims.
Ski, for her part, later apologized for her remarks, noting that she had spoken to Halle, who told her “ain’t nothing going on.”
The social media messages have since been deleted.
March 2023
The twosome proved they were going strong one month after facing cheating rumors when they stepped out at the Vanity Fair Oscar party in Los Angeles.
April 2023
“Experiencing deep love for the first time in my life is something I feel has opened a whole new world for me creatively,” she gushed to British Vogue of her relationship. “What it feels like to love someone other than your family, like somebody you may not have known two years ago but now they’re the center of your world.”
She continued: “I like all of the scary feelings that come with that. I like the suspense, the not knowing what’s going to happen, and I feel like that’s what I’m supposed to be going through in womanhood.”
May 2023
“On my last day of press like…” Halle captioned a TikTok video of herself kissing DDG.
July 2023
Rumors of problems in their relationship only increased after DDG dropped the song “Famous,” in which he appeared to call out Halle.
“Filmin’ a movie now you kissing dudes / You know I love you a lot / I don’t give a f—k if that s—t for promo / I don’t wanna see this s—t no more / Why is y’all holdin’ hands in the photo?” he raps on the track, seemingly referring to Halle holding hands with Little Mermaid costar Jonah Hauer-King on the red carpet. “You know I’m insecure, that’s a no-no.”
However, DDG clarified that the track was “just a song.” “It’s just music y’all. Just how movies is just movies, songs is just songs,” he said in a video, per The Shade Room.
September 2023
Halle and DDG proved they were going strong while attending Diddy’s listening party for The Love Album in New York City together. The couple also appeared at shows during Milan’s Fashion Week, notably at Dolce & Gabbana for their Womenswear Spring/Summer 2024 collection and at the Gucci Ancora show.
November 2023
Halle and DDG twinned in black at the red carpet premiere of Beyoncé’s Renaissance concert film. (Halle and her sister Chloe count the Grammy winner as a mentor.)
January 2024
DDG confirmed on January 6 that their first baby, son Halo, had arrived by dedicating a verse in his new rap freestyle to the newborn.
“Silver Spoon kid / I know Halo won’t want for nothing,” DDG rapped. “He cryin’ / his mama coming / she’s stronger than Wonder Woman.”
October 2024
DDG revealed that he and Bailey amicably called it quits.
“This decision was not easy, but we believe it’s the best path forward for both of us. I cherish the time we’ve spent together and the love we’ve shared. Despite changes in our relationship, our love for each other remains deep and true,” the rapper wrote via his Instagram Story. “We are still best friends and adore each other. As we focus on our individual journeys and our roles as coparents, we cherish the bond we’ve built and the beautiful moments we shared.”