Halle Bailey and DDG’s Complete Relationship Timeline

Actress Halle Bailey and YouTube star and musician Darryl Dwayne “DDG” Grandberry Jr. have been together for about a year and a half. But they have been aware of one another for much longer as two young people who came up in the entertainment business.

The pair were first romantically linked in January 2022, after they were seen together at Usher’s residency in Las Vegas. Things became official a few months later on Instagram, when DDG wished Bailey a happy birthday in a now-deleted video. He wrote at the time, “Happy Birthday to the beautifulest, the flyest, the sweetest ❤️ love you forever 🥺💎.”

Here’s the complete timeline of their relationship so far.

The couple meet up in Las Vegas to see an Usher concert and footage taken of them by other concertgoers started circulating online. The event was so popular that the word “Usher” began trending on Twitter. The video shows DDG drinking a beverage as Bailey talked to him excitedly, seeming to exclaim, “Oh my god!” over what was taking place onstage.

Later, the musician shared photos with the new couple on his Instagram Story, in which DDG has his arm around Bailey’s shoulders.

For their red carpet debut, the couple attended the BET Awards together.

“I have my boo with me today,” Bailey told Extra correspondent Rachel Lindsay at the event. “We’re so excited. We’re gonna have so much fun just supporting Chloe [for her solo performance]. It’ll be great!”

She added: “I was so nervous, like, we’re trying to figure out what to wear [and] all this stuff.”

DDG made an appearance in a TikTok video with Bailey that month as well, in which they look very intimate and are doing some vocal warm-ups together.

“Singing lessons with @DDG,”she wrote in the caption.

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The couple attended Variety’s Power of Young Hollywood Event in L.A.

They attended the the 5th annual Wearable Art Gala.

In an interview with Essence, Bailey discussed how she has been a fan of DDG’s for a long time.

“I’ve been a fan of his for years,” she said. “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.”

Bailey had seen his videos in 2015, but explained she “forgot about him” for a while.

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.”

DDG accompanied Bailey to the premiere of Avatar 2: The Way of Water.

In February 2023, fans started speculating about their relationship after DDG’s ex-girlfriend Rubi Rose tweeted about seeing her ex’s new girlfriend wear her old clothes in a tweet. She didn’t mention either DDG or Bailey by name, but it was quickly noted that Bailey was wearing a black and white T-shirt in an Instagram post that Rose had been seen in back in 2020.

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DDG added fuel to the fire when he unfollowed Bailey and tweeted, “All these girls the same, ain’t no way.”

He later clarified that no cheating had gone down.

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In a since-deleted tweet, Bailey also addressed the rumors, writing, “The devil is working lol Please don’t feel into the lies, especially from a third party. Stay blessed everyone.”

DDG has since re-followed Bailey.

In March, the two attended the Vanity Fair Oscar party together in Los Angeles.

Bailey told British Vogue that love has changed her creative life as well.

“Experiencing deep love for the first time in my life is something I feel has opened a whole new world for me creatively,” she said. “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.”

But it hasn’t been easy to manage her private life while her star was rising, particularly with the focus she received during press for Disney's live action remake of The Little Mermaid.

“There’s a lot of eyes on me now, especially with what’s to come,” she said. “And sometimes I wish I didn’t have so many eyes on me, especially experiencing something like this for the first time.”

In May, as the work of promoting her Disney film wound down, Bailey shared a TikTok of herself kissing her boyfriend, writing in the caption, “On my last day of press like…”

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On July 14, DDG faced considerable backlash after the release of his new song “Famous,” which seem to take aim at Bailey’s press tour for her role as Ariel in The Little Mermaid.

“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.”

She held hands with co-star Jonah Hauer-King in May, the Prince Eric to her mermaid at the London premiere of their movie. DDG went on in his song to say:

“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.”

Early in September, Bailey and DDG attended the The Love Album listening party in New York City together.

They also made appearances at several fashion shows during Milan Fashion Week, first at Dolce & Gabbana for the brand’s spring/summer 2024 collection.

They were also seen at the Gucci Ancora show on September 22 seated next to Hanni from NewJeans.

Bailey and DDG attended the Glamour Women of The Year Awards in London together, where The Little Mermaid star was being honored. Bailey wore a strapless black dress with a full petticoat under the skirt that flared it out around her waist amid rumors of her pregnancy.

She was also photographed out in a casual outfit the week before, wearing a sweater and sweatpants, further prompting theories about whether or not she’s expecting.

On Christmas, Bailey received a series of expensive gifts from DDG. The rapper shared some clips of the unwrapping on Snapchat, saying he spent “spent $500,000 on Christmas.”

He gave his girlfriend an Hermès Birkin bag and a yellow gold Tiffany & Co. HardWear bracelet to start, valued at $12,700.

“I can’t believe you got this,” she said in a clip. “This is the one we tried on [at the store] just to play and just to pretend.”

He also gave her a pair of Balenciaga snowboots and pants.

The Color Purple star also spoiled her boyfriend, gifting him with a pair of diamond stud earrings.

On Saturday, January 6, Bailey announced that she and DDG had welcomed a baby boy together on Instagram. She posted a photo of her hand holding the newborn’s fist over her boyfriend’s, sharing that they had named their son Halo.

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“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,” she wrote in the caption. “welcome to the world my halo 🥰👼🏽 ✨.”

She added jokingly, “the world is desperate to know you 😉🤣♥️.”

Then, on January 15, she shared some previously unreleased maternity shoot footage, which The Little Mermaid actress staged underwater. Some video clips and photos were edited together, showing her in two different outfits, one in sheer white and another in metallic silver. The Reel also offered a glimpse of her belly while she was still pregnant.

In the caption, she wrote, “🧜🏽‍♀️missing my belly already 💜but i obviously had to do underwater pics 😉”

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On February 1, Bailey spoke with People and shared how she and DDG landed on “Halo” as the name for their son.

“It was actually my boyfriend’s idea. He’s the one who came up with his name,” she recalled. “We just agreed, and we loved it. I love the name Halo.”

People asked the singer if there was any connection between her son’s name and the song “Halo” from her mentor Beyoncé’s 2008 album I AM...SASHA FIERCE.

“He for sure has a theme song,” Bailey laughed.

DDG, meanwhile, shared later in February that their son Halo was a surprise baby. “We weren’t aiming for a baby, but it just kinda happened,” he said on The Jason Lee Show. “What are we going to do?”

He added that he and Bailey made their decision based on both their interest in raising a child. “Both of us have the same interest in being parents,” he said. “And I feel like she always wanted to be a mom. We always kind of just give off that energy, and I always wanted a kid. So, from there we just decided to go through with it.”

In March, Bailey celebrated her 24th birthday in Hawaii with baby Halo and DDG. She shared pictures of the beautiful scenery, her purple and yellow bikinis, and the family enjoying mud baths. She captioned the pics, “this is 24.”

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In early April, breakup rumors began swirling around DDG and Bailey after they both unfollowed each other on Instagram. They also each took down most of the pictures that they had posted together.

However, according to TMZ, a rep for Bailey reached out to clear the air and state that the couple is in fact still together. While the rep did not explain why they decided to unfollow each other, they made it known that they have are still going strong and continue to parent their three-month-old son together.