“I already told y’all, Harley and I have split. It’s life, it happens, but she’s still family. I’ll always love her no matter what.”
Now that Daryl “DDG” Grandberry has confirmed his breakup with Halle Bailey, fans aren’t too surprised. Their relationship had its ups and downs from the start, and today, we’re diving into all the red flags that were there all along. But hey, before Halle’s sister Chloe comes for us for talking about her sister
So, here’s how it all started: back in 2015, Halle stumbled across one of DDG’s music videos and thought it was cool, but he kind of slipped off her radar. Fast forward a few years, Halle started vibing with one of his newer songs. Around the same time, DDG was already creeping on her Instagram. When he saw her post about one of his favorite 50 Cent tracks, he slid into her DMs, and they hit it off. Halle even admitted she’d been a fan of his YouTube channel and music for a while. After some online chatting, they made their first public appearance together at an Usher concert in January 2022. Funny enough, DDG later told The Shade Room that Halle had to carry most of the conversation on their first date. By March 2022, they officially went Instagram public.
In May 2022, DDG tweeted, “All I’m missing in my life is a child.” Fans quickly jumped to conclusions, thinking he was hinting at wanting to have a baby with Halle Bailey. Many of them warned Halle to steer clear of him. But later on, DDG opened up about how much Halle had changed his life for the better. He said she motivated him to be a better person and work harder, especially as her career was skyrocketing. Halle had just landed the role of Ariel in The Little Mermaid and was also working on her first solo album after branching out from making music with her sister, Chloe.
The two even worked on some music together, and a few months later, DDG released a song called “In Love with a Mermaid,” which seemed to be dedicated to Halle. In the song, he raps, “I fell in love with you from the start / You know you’re amazing, you a star / Fell in love with you because of who you are / Was looking like a fool but you saved me from the dark / The VVS’s cool, should’ve bought your ass a car.”
Some younger fans admired their relationship, but Halle’s more experienced supporters saw red flags right away. By February 2023, DDG had removed all of Halle’s photos from his Instagram, and they both unfollowed each other. This sparked rumors that there was trouble in paradise. DDG added to the speculation by tweeting, “All these girls are the same, and all you ninjas are the same too.” He did re-follow Halle after the tweet went viral, but fans were still convinced he was stirring up drama to overshadow Halle ahead of The Little Mermaid release, and many urged her to leave him for good.
Behind the scenes, DDG’s life was even more chaotic than people realized. His ex-girlfriend Ruby Rose posted some direct messages he sent her on the same day he tweeted about how “all girls are the same.” In those messages, he asked Ruby if she was still in L.A. When she pointed out that he was hitting her up while dealing with drama with Halle, DDG replied, “LOL, you right, let me go heal first.” After being called out, he tweeted, “I know it looks bad, but it ain’t what it seems. Swear to God, it’s just evil.” Later, when The Shade Room started reporting on the situation, DDG jumped into the comments, claiming Ruby’s screenshots were fake and painted her as an ex who was still obsessed with him.
There were definitely some problems with his story. First off, he slid into Ruby’s DMs trying to meet up, and she was the one who turned him down. A lot of people online hoped this public embarrassment would be enough for Halle to finally walk away, but it looked like she was willing to let him play her for a fool. She tweeted, “The devil is working LOL. Please don’t feed into the lies, especially from a third party. Stay blessed, everyone.” One user chimed in, “I remember when I was this easily manipulated,” and another advised, “Halle, stand up, baby. Him going back and forth like this should tell you everything you need to know.”
Then, on April 1, 2023, DDG shared a sonogram with the caption, “Can’t wait to be your dad.” Fans immediately assumed that Halle was the mother and went to her Instagram, calling her a “dummy” for getting involved with him. About four hours later, DDG returned to Twitter to say it was just an April Fool’s joke, but no one was laughing. Even though he’s known for pulling pranks and trolling online, some people couldn’t shake the feeling that this was his way of hinting at wanting to start a family with Halle.
By May 2023, Halle was open about her feelings for DDG in an interview with People magazine, calling her relationship a transformative experience. But her “internet aunties” weren’t buying it. Many believed that Halle could do way better and didn’t think DDG was worthy of her. Whenever she brought him along as her plus one to industry events, online critics were quick to comment. Some thought he was just using her to gain access to her connections in the entertainment world, while others urged her to ditch him before the release of The Little Mermaid, fearing he might embarrass her in some way.
In another interview with Glamour magazine that same month, Halle admitted she heard all the chatter and that it sometimes made navigating the entertainment industry tough for her. To protect her peace and sanity, she decided to keep her personal life more private moving forward. However, DDG, being a YouTuber, clearly had other plans and wasn’t about to stop sharing snippets of their relationship online.
When The Little Mermaid hit theaters in May, Halle caused a stir at the UK premiere when she was spotted holding hands with her co-star Jonah Hauer-King, who played Prince Eric. Fans went wild over the photos, urging Halle to leave DDG behind and explore a romance with Jonah instead. DDG initially kept quiet about it all, but that didn’t last long. In July 2023, he dropped a song called “Famous,” which made it pretty clear—he was feeling jealous of Halle’s success. If you’re not one to follow his music, you might want to check it out; it definitely adds some drama to the story!
The song kicks off with lyrics like, “Me, me, me, me, I’m just trying to figure out what we’re going to do / How are we going to make it to the top? / We’re filming a movie, and now you’re kissing other guys / You know I care about you a lot / I don’t give a [ __ ] if that’s just for promotion / I really don’t want to see this anymore / Why are you holding hands in that photo? / You know I’m insecure, and that’s a no-go.” He talks about how falling in love with someone famous has been incredibly tough for him, and even though he’s thinking about leaving the relationship, he feels way too attached.
The internet didn’t hold back, roasting him hard and calling him a failed YouTube rapper. One commenter labeled him an “insecure little man” and a “total loser.” Her fans were shocked that he was making her rising career a circus, and a Reddit user slammed him for throwing a fit during such a big moment for her. In response to the backlash, he posted a video saying the song was just a song and that everyone should chill out. It felt like another one of his stunts, to be honest.
Halle’s solo debut single, “Angel,” dropped at the beginning of August. Instead of her fans celebrating her new music, all anyone could talk about was rumors that she’s pregnant. A writer at Toya’s World blog pointed out that if Halle is pregnant by a paranoid, immature rapper who can’t handle her success, that’s on her. Later, during a Snapchat Q&A, Halle told her fans she’s been trying to stay off social media while preparing for the arrival of her son in October 2024.
Things got even more complicated when Disney pulled Halle from consideration for an Oscar nomination for Best Original Song for her track “For the First Time” from The Little Mermaid. Many speculated that Disney made this move because she’s pregnant out of wedlock, wanting to avoid any tarnishing of their wholesome image. Fans dragged Halle for messing up her Disney opportunity for someone like DDG, who they see as immature.
The couple announced the arrival of their son, Halo, in an Instagram post back in January 2024. DDG opened up to Jason Lee about how the pregnancy took them by surprise. He said, “We weren’t planning on having a baby, but when you’re in my position and you’re making a lot of money, you start to think you can handle anything life throws at you. So here we are.”
However, he later admitted to Complex that becoming a father brought unexpected challenges that strained his relationship with Halle. He confessed that she was still the main breadwinner, and he was having a tough time keeping up. By August 2024, DDG revealed that he was living separately from Halle, and they were working on their co-parenting arrangement.
It’s clear they’ve been through a lot in their two years together, but at least they’re committed to being good co-parents for Halo. Now that it’s all said and done, what do you think, besties? Should Halle have recognized the signs from the start? Can DDG bounce back from everything he’s done? Let me know your thoughts in the comments below!