Skai Jackson had a successful run as a Disney Channel star, but her transition into adulthood hasn’t been without its challenges—especially when it comes to her dating life. Today, we’re taking a closer look at her messy relationship history. Oh, and before we dive in, make sure to check out RRGSnacks.com for all your favorite treats, like Western barbecue bacon jerky, freeze-dried goodies, butter toffee peanuts, and gummy sour peach rings. You don’t want to miss out!
Kid Trunks: The Beginning of the Drama
Skai’s first public relationship was with rapper Kid Trunks back in late 2017. Things seemed fine at first, but by November 2018, their romance had officially run its course. Kid Trunks even went on Instagram Live to make it clear he wanted nothing to do with Skai anymore, saying:
“And everybody, go tell this little-ass girl to stop bothering me. Like, leave me alone, bro. My girl is a whole grown-ass woman, bro. You are a little-ass girl still, bro. Please leave me alone, bro.”
It wasn’t exactly the most graceful breakup, to say the least.
Famous Jay: A Quick Fling
Not long after things ended with Kid Trunks, Skai started dating another rapper, Famous Jay. This relationship lasted about five months before it fizzled out, and Skai moved on to her next romance.
Smooky Margielaa: A Blink-and-You-Miss-It Relationship
In 2019, Skai was linked to rapper Smooky Margielaa. However, their relationship reportedly lasted only a month before they decided to call it quits.
Lil Keed: A Love Triangle Gone Wrong
By December 2019, things took a dramatic turn when a woman came forward accusing Skai of messaging her boyfriend, rapper Lil Keed. At the time, Skai was 17, and Lil Keed was 21. According to the woman, Skai and Keed were secretly seeing each other and planned to go public once Skai turned 18. She claimed that Skai had even sent suggestive DMs, including one where she referred to herself as his “fish taco.”
The woman didn’t hold back, warning Skai to “find something safe to do” and accusing her of “playing with fire.” The drama set social media on fire, with fans and critics alike chiming in on the situation.
That was the end of whatever Sky and Lil Keed had going on. Sadly, Lil Keed passed away in 2022 at just 24 years old. By that time, people had already started to notice that Sky seemed to have a thing for rappers, and they couldn’t help but question her taste in men.
In early 2020, Sky took to Instagram and openly said:
“Can somebody hook me up with NBA YoungBoy? He just so fine to me.”
Lord, help us. Not NBA YoungBoy! This man has a troubled past, and here she was shooting her shot with the “serial baby daddy.”
At the time, Sky was 17, while YoungBoy was a 20-year-old father of four. Of course, this didn’t sit well with Bhad Bhabie, who was also 16 at the time and had some history with YoungBoy. Bhad Bhabie wasn’t having it and clapped back, calling Sky a “Disney thot.”
“Not a Disney thot!”
Bhad Bhabie wasn’t done there. She took to Instagram to vent:
“She literally do this with every dude I talk to. Ough!”
Sky, trying to avoid more drama, tweeted that she wasn’t here for negativity. But Bhad Bhabie kept going, writing on her Instagram story:
“So y’all telling me it’s okay for someone to play the innocent role in front of the main crowd, but in real life, they making fer accounts to talk bad about people they try and be like so bad.”
Wait, what’s a “fer” account? Is she talking about a fake Instagram account? These kids are constantly coming up with new slang, and I kinda love it.
Bhad Bhabie clarified that it wasn’t just about Sky crushing on YoungBoy. She was upset that Sky had also pursued several of her exes. She added:
“This issue—stop believing that this is innocent.”
Things got even messier when Sky’s mom and Bhad Bhabie’s mom jumped into the drama to defend their daughters. Sky eventually sought a restraining order against Bhad Bhabie after Bhad Bhabie made violent threats:
“I ain’t tripping ’cause I’mma see her. I’mma see her at the perfect time, and I’mma dog her… I’ll literally kill you. If I get my hands on you, it’s over.”
Eventually, Sky dropped the restraining order, telling TMZ:
“Now that she’s made the decision to work on herself through rehab and therapy, I’m pleased that I don’t need to extend my restraining order.”
Sky moved on from her NBA YoungBoy crush and by early 2021, she was linked to rapper NLE Choppa. That didn’t last long, though, and soon after, she was involved with Daniel Julez Smith Jr.—Solange’s son and Beyoncé’s nephew. Sky was 18, and Julez was 16.
Oh no, absolutely not! This was getting out of hand.
By the time the world caught wind of their relationship, it was already over. Julez claimed Sky had cheated on him and confirmed their breakup wasn’t amicable. Alleged screenshots from a group chat showed Julez describing their relationship as “complicated” while also confirming their fling.
When a friend pointed out their age difference, Julez replied:
“Age doesn’t matter.”
Oh, but it does. Just ask R. Kelly—on second thought, don’t.
Then, an intimate video of Sky and Julez surfaced online. Many assumed Julez was behind the leak.
A few months later, in July 2021, Sky was spotted watching a live video of prison inmates. She jumped into the comments to write:
“Tell the one in gray I’mma get him out.”
What in the Love After Lockup is happening here? Was Sky into jailbirds? It seemed like she might be, leaving people both confused and entertained by her unpredictable love life.
Let’s fast forward to March 2024. Sky made a soft launch of her new relationship by posting a picture of her new guy. She made sure his face was hidden, but she didn’t quite think to hide his tattoos. Turns out, those tattoos gave it away. Her mystery man was none other than DeAndre Bergen, also known as Yerky Yerky.
Yerky Yerky? Seriously, what kind of name is that? Makes me think of some western-style bacon jerky.
It wasn’t long before their relationship took a turn for the worse. By July 2024, the police were called to Universal CityWalk after security saw Sky pushing Yery multiple times. Sources told TMZ that Sky and Yery denied anything physical had happened, claiming they were happily engaged and even expecting a baby.
But the cops weren’t convinced. After reviewing security footage, they arrested Sky right on the spot. The case was eventually dropped by the DA because there wasn’t enough evidence. People initially thought Sky and Yery had made up the pregnancy story to avoid any consequences. But then, months later, photographers snapped shots of Sky with a baby bump.
Who would’ve thought? Sky Jackson, a baby mama? On November 1, 2024, Sky and Yery were spotted walking together, having a heated conversation. A photographer followed them until Sky dropped Yery off at a Holiday Inn entrance.
A few days later, on November 12, 2024, Sky confirmed her pregnancy with People magazine. She shared:
“I’m thrilled to begin this new chapter in my life, embracing motherhood and diving into new acting projects. My heart is so full.”
One thing that stood out to fans was that Sky didn’t mention Yery at all in the announcement, and he wasn’t part of her pregnancy photo shoot.
Sky’s moment of joy was quickly overshadowed by a Facebook post, allegedly written by Yery, which said:
“Well, I’m salty I got this dumbass Disney Channel pregnant. I hate this Chanel.”
Did he mean Channel and just misspelled it? After the post went viral, Sky and her mom quickly jumped online to say that Yery’s Facebook had been hacked. But Yery wasn’t backing down. He took to his own social media and posted:
“Boy, y’all need to stop doing that girl like bro. What? I ain’t do [ _ ]. I can do whatever the [ _ ] I want. Baby girl, you ain’t know? I’m good for domestic violences. On life, we both go to jail beating on each other.”
If this doesn’t scream drama, I don’t know what does. It only escalated further when, during a Facebook Live session, Yery said:
“He need his ass beat. Somebody grab my belt. Give me my BT right now!”
Then, on November 13, a video surfaced showing Yery being arrested. The details of the charges are still unclear, but things were getting even messier. On the same day, another man stepped forward and accused Yery of being gay, demanding that he tell the truth about their relationship:
“Just sitting quiet, no more. Sky Jackson’s baby daddy needs to go ahead and tell the truth about what me and him got going on. Like, you going live doing all this about her, but you need to tell her why you doing all that and who you really like.”
The man added:
“I don’t want beef with Sky, but I’ve been quiet too long. He tells me, ‘Don’t text her. Don’t DM her.’ But it’s too much now. I’m going to start running my mouth. I get she’s pregnant, but he needs to tell the truth before I do. If not, I’ll show the videos and pictures when I was up at his house.”
He ended with:
“Sky Jackson, if you see this, don’t overdo too much. It’s normal. Everybody likes what they like. But yeah, I’m about to post everything.”
Not only is this man allegedly a criminal, but now there’s speculation about him being on the down-low? Wow.
Meanwhile, the internet dug into Yery’s past and found that he already had at least two children with another woman. His children’s mother also posted videos of his legal troubles, raising more concerns about Sky’s choice of baby daddy.
While the exact charges Yery faced aren’t clear, some sources suggest it might have been related to selling substances.
At the end of the day, Sky is an adult who can make her own choices. But this whole situation feels like a ticking time bomb. Many of her fans are worried that she’s bringing a child into what seems like a toxic environment.
For now, all we can do is sit back, grab some snacks, and hope for the best for Sky and her baby.