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Halle Bailey and Boyfriend DDG’s Complete Relationship Timeline

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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 much longer as two young people who came up in the entertainment business.

The pair were first linked romantically in January 2022 after they were seen together in Las Vegas while at Usher’s residency there. Things became official a few months later on Instagram when DDG wished her 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.

January 2022

The couple meet up in Las Vegas to enjoy an Usher concert and footage taken of them by other concert goers started circulating online. It was so popular, 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 on stage.

Later, the musician shared photos with the new couple on his Instagram Stories in which DDG has his arm around her shoulders.

June 2022

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

2022 bet awards arrivals

Prince Williams//Getty Images

“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.

August 2022

The couple were together at the Variety Power of Young Hollywood Event in Hollywood together.

20th century studio's

Axelle/Bauer-Griffin//Getty Images

October 2022

They attended the the 5th annual Wearable Art Gala.

5th annual wearable art gala honoring angela bassett and mark bradford

Unique Nicole//Getty Images

November 2022

In an interview with Essence, Bailey talked about how she has been aware of DDG and a fan 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.”

December 2022

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

20th century studio's

Axelle/Bauer-Griffin//Getty Images

February 2023

In February of 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.

Some took this to mean that DDG had recently cheated with Rose, somehow taking her shirt in the exchange, but that doesn’t seem to be what she is saying. DDG added fuel to the fire, however, when he unfollowed Bailey and tweeted “All these girls the same, ain’t no way.”

He later wrote that no cheating had gone down.

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 her.

March 2023

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

2023 vanity fair oscar party hosted by radhika jones arrivals

Jon Kopaloff//Getty Images

April 2023

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.”

May 2023

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…”

July 2023

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.”

September 2023

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

love album

Shareif Ziyadat//Getty Images

They also made appearances at several fashion shows during Milan’s Fashion Week, first at Dolce & Gabbana for their Womenswear Spring/Summer 2024 collection.

dolcegabbana arrivals milan fashion week womenswear springsummer 2024

Jacopo Raule//Getty Images

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

gucci ancora front row milan fashion week springsummer 2024

Daniele Venturelli//Getty Images

October 2023

Bailey and DDG attended the Glamour Women of The Year Awards in London together, where The Little Mermaid star was being honored. Rumors have been circulating that the 23-year-old is disguising a pregnancy while making public appearances with strategically tailored clothing. New pictures of them on the red carpet have fanned those flames. Bailey wore a strapless black baby doll dress with a full petticoat under the skirt that flared it out around her waist, potentially hiding a baby bump.

glamour women of the year awards 2023 arrivals

Mike Marsland//Getty Images

She was also photographed out in a casual outfit the week before, wearing a sweater and sweat pants that make it look as though she may indeed be expecting. Or at least wearing much looser clothing than usual.

December 2023

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 snow boots and pants.

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

Headshot of Aimée Lutkin

Aimée Lutkin

Aimée Lutkin is the weekend editor at ELLE.com. Her writing has appeared in Jezebel, Glamour, Marie Claire and more. Her first book, The Lonely Hunter, will be released by Dial Press in February 2022.

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