From an R&B prodigy to a Disney princess, 23-year-old Halle Bailey is at the peak of her career and just getting started. However, with the teased pregnancy and recent birth of her son Halo, the Georgia native has experienced some big life changes. And ultimately, fans are left wondering who is Halle Bailey’s boyfriend?
While many have shipped her with “The Little Mermaid” co-star Jonah Hauer-King, she was formerly dating YouTube star and fellow musician, Darryl Dwayne “DDG” Grandberry Jr., all the way up until October 2024. Here’s everything we know about the celebrity couple and how their love came to be, and how it ended.
The Two Were First Spotted in January 2022
Bailey and DDG’s relationship began on social media when the rapper slid into her DMs and took her on a date. However, she was well aware of him before he finally took the initiative. It was the ultimate dinner and a movie as the two went to see the movie “Dune” and grabbed a bite. However, it wasn’t until a few months later that the world got a first glimpse of the burgeoning couple.
Even though rumor mills were buzzing about the couple’s potential pairing, both were fairly tight lipped until March 2022 when the couple made their relationship Instagram official. DDG shared a birthday shoutout to the chanteuse — confirming what everyone had been speculating on for the past few months.
Usher’s residency in Vegas has pulled in some pretty big names as audience members, and Bailey was certainly not going to let herself miss out on the fun. It was date night for the inconspicuous duo as they were spotted by concert-goers, seeming pretty cozy and cuddled up. The internet was quick to get an ID on Bailey’s mystery man, setting social media ablaze.
Who Is DDG?
26-year-old Darryl Dwayne “DDG” Grandberry Jr. can accredit YouTube for his rise to fame, gaining popularity through vlogs and amassing over 7.5 million subscribers. Born in Pontiac, Michigan, in October 1997, he was valedictorian of his high school graduating class and took education very seriously. However, making $20,000 a month via YouTube was enough to convince the artist to drop out of college and move to Los Angeles.
Eventually signing to Epic Records, his hip-hop career quickly became his main focus, releasing a project nearly every year since 2018.
They Made Their Red Carpet Debut in June 2022
Stunting on the red carpet together is a big move for young couples in Hollywood, and the warmth of summertime had Bailey ready to take that step. For their red carpet debut, the couple attended the 2022 BET Awards together to support sister Chloe Bailey, where she gushed to an “Extra” correspondent, “I have my boo with me today.”
The couple was spotted at other high-profile events following that including the WACO Wearable Art Gala in 2022, sitting front row at Milan Fashion Week in 2023, as well as attending the Vanity Fair Oscars afterparty a year later in March 2023.
They’re Not Shy About Their Love
The young couple in love has certainly not held back from showing glimpses of their romance to the world, including this very adorable TikTok of them warming up vocals together. Bailey has even made some appearances on DDG’s YouTube channel, showing that she’s in full support of his creative endeavors. Bailey even appeared in DDG’s music video “If I Want You” that dropped August 2022. Meanwhile, she was also referenced in the track “Famous” where DDG addressed the on-screen kiss with costar Hauer-King. Most famously, the lines “Filmin’ a movie now you kissing dudes / You know I love you a lot / I don’t give a f— if that s— for promo / I don’ wanna see this s— no more” before continuing with “Why is y’all holdin’ hands in the phone? / You know I’m insecure, that’s a no-no.”
DDG Supports Bailey’s Career
While his lyrics pointed to jealousy, DDG has been vocally supportive of Halle Bailey’s career. He’s quoted as saying “I’m very proud of her. And I’m just happy to see it…sometimes I’m even more excited than anybody else. Just seeing it and seeing everything that she dreamed of coming to life, it’s really dope.” when he spoke with People magazine about her lead role in “The Little Mermaid.”
Bailey Opens Up in November 2022
Beyond attending red-carpet events and sharing cute pictures online, we didn’t know much about the partnership— that is, until her interview with “Essence.”
“I’ve been a fan of his for years,” she shares about DDG. “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 some time had passed between her spotting him and their actual connection, it seems as if they were on the same wavelength, as she went on to share, “I saw that he was dropping music, and I really gravitated toward this one song. Coincidentally he messaged me— and the rest is history.”
She also opened up about how protective she felt over their relationship to “British Vogue,” sharing, “Experiencing deep love for the first time in my life is something I feel has opened a whole new world for me creatively. Sometimes I wish I didn’t have so many eyes on me, especially experiencing something like this for the first time.”
They Couldn’t Avoid the Drama
It hasn’t all been paradise, though. While he was supportive during her “Little Mermaid” press run, DDG couldn’t help but feel a type of way watching Bailey and co-star Jonah Hauer-King get cozy on the red carpet, letting his music be an outlet for his emotions. “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,” the lyrics go. “Why is y’all holdin’ hands in the photo? / You know I’m insecure, that’s a no-no.”
Fans didn’t exactly love his stance, as the song continues, “Fall in love, I hate that s–t / Knockin’ me off my grind, I can’t f–k with relationships/ I ain’t even got enough time in a day for me to chase a bitch / I don’t even ask for much, I ask you to do the basic s–t / Hardest thing I did was fall in love with a famous b-tch.” Luckily, it seems as if the drama was handled behind closed doors and the two came back together even stronger.
The Couple Welcomed a Baby in 2023
First comes love, then comes… pregnancy rumors? Much of 2023 saw Halle Bailey attempting to hide a baby bump whenever she was spotted at red carpet evens. From strategically loosely fitting outfits to badly photoshopped Instagram photos, the singer worked overtime to maintain some level of privacy. However, in January 2024, the couple announced the birth of their first child together, a son they named Halo.
DDG gushed that Halo was his “biggest blessing by far” in an Instagram post while Bailey’s post chimed in saying “Even though we’re a few days into the new year, the greatest thing that 2023 could have done for me was bring me my son.” Both couples chose an adorable shot of young Halo’s hand wearing a gold ID bracelet with his name on his wrist — while the couple’s hands are captured in the shot.
Their 2024 Split
Though things seemed to be shaping up into a fairytale romance for Bailey and DDG, the latter revealed in an October 2024 Instagram Story that they’d parted ways, shattering the dreams fans might have had for a happy ending for the pair. “We are still friends and adore each other,” DDG reports. “As we focus on our individual journeys and our roles as co-parents, we cherish the bond we’ve built and the beautiful moments we’ve shared.”
At the moment, there’s been no news of Halle Bailey dating anyone else – understandable given how recent the breakup was. Time will tell who might next have the honor of being Halle Bailey’s boyfriend.