Honestly, keeping track of the Kardashian dating tree is like trying to solve a Rubik’s cube while riding a rollercoaster. We all know Kim’s high-profile marriages and Khloé’s endless Tristan drama, but the "forgotten" brother has a track record that is surprisingly—and sometimes devastatingly—chaotic. If you’re looking into rob kardashian who dated who, you’re probably expecting a list of models and the usual reality TV suspects.
But it’s deeper than that.
For a guy who has spent the last decade practically living as a ghost in his own family's empire, his romantic history is the very thing that defined his public rise and his heartbreaking retreat from the cameras. From Disney stars to pop royalty and the explosive saga with Blac Chyna that nearly took down the Kardashian brand, Rob’s love life isn't just gossip. It’s a roadmap of how he ended up where he is today.
The Early Days: When Things Were Actually Normal (Kinda)
Before the socks, before the seclusion, and before the Instagram rants, Rob was the "normal" one. He was a USC graduate with a bright smile and a spot on the family’s growing reality show.
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Adrienne Bailon (2007–2009)
This was the big one. If you grew up watching early Keeping Up With the Kardashians, you remember Adrienne. She was a Cheetah Girl, a Disney darling, and she was genuinely part of the family. They were young, they were cute, and they even got each other's names tattooed on their bodies.
But it ended in a mess.
Years later, Adrienne admitted that the pressure of being "the Kardashian girlfriend" was a lot. But the real kicker? Rob cheated. He admitted it on the show, and it’s arguably the moment his public image started to shift from "charming younger brother" to "guy who makes some questionable choices." Adrienne eventually got the tattoo removed, which, let’s be real, is the universal sign for I am never going back there.
The Rita Ora Disaster (2012)
Fast forward a few years. Rob is at his peak physical fitness, he’s doing Dancing with the Stars, and he starts dating British pop star Rita Ora. They were notoriously private—until they weren’t.
When they broke up in late 2012, it wasn’t just a "we grew apart" statement. Rob went on a Twitter rampage that felt like the digital version of a house fire. He accused her of cheating on him with "nearly 20 dudes" while they were together. Rita basically shrugged it off, later telling The Sunday Times in 2020 that she literally "forgot" they even dated.
Ouch.
The Blac Chyna Era: A Relationship That Changed Everything
If we’re talking about rob kardashian who dated who, we have to spend time on the Chyna of it all. This wasn't just a relationship; it was a tactical nuclear strike on the Kardashian family dynamic.
At the time, Blac Chyna was the ex-fiancée of Tyga, who was dating Rob’s youngest sister, Kylie Jenner. The messiness was astronomical. When Rob and Chyna went public in early 2016, his family supposedly found out via social media.
- January 2016: They start dating.
- April 2016: They get engaged.
- May 2016: They announce they’re expecting a baby.
- November 2016: Dream Renée Kardashian is born.
It moved at lightning speed. And it crashed just as fast. Between the "Rob & Chyna" reality show and the constant Instagram breakups, it was exhausting to watch. The relationship ended in 2017 with a series of lawsuits, restraining orders, and "revenge porn" allegations that Rob later had to settle. It was dark, it was public, and it’s the primary reason Rob hasn't been a regular on TV for years.
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The "Invisible" Years: 2018 to 2025
After the Chyna fallout, Rob became the "Wizard of Oz" of the family, as Khloé recently put it. He stayed behind the curtain. But that doesn’t mean the dating rumors stopped.
For a while, every time a woman was spotted in a 10-foot radius of a Kardashian party, the internet claimed it was Rob’s new girlfriend. There was Natti Natasha (the Dominican singer) who flirted with him on Twitter in 2019. There was Alexis Skyy (from Love & Hip Hop), who cooked him dinner and posted it on her story just to spite Blac Chyna.
But none of it was "real."
In 2024 and 2025, Rob finally started surfacing more on social media. He looked healthier. He looked happier. But his dating life remained a total enigma. He’s been linked to various influencers, but nothing has ever been "Kar-Jenner Official."
The Shocking 2026 Update: Are He and Chyna... Back?
Here is where things get wild. As of early 2026, the biggest rumor in the world of rob kardashian who dated who is actually a blast from the past.
Angela White (the artist formerly known as Blac Chyna) has undergone a massive lifestyle transformation. She’s removed her fillers, leaned into her faith, and most importantly, she and Rob have become the "gold standard" of co-parenting for Dream.
Recently, she called Rob her "person."
They’ve been spotted at Universal Studios laughing like they never spent years in a courtroom. While sources close to the family insist they are just "best friends" and dedicated parents, the chemistry is undeniable. Chyna even hinted in a late 2025 interview that she’d be open to more kids with Rob.
Is it a reconciliation? Or just two people who finally grew up?
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What Most People Get Wrong About Rob’s Dating Life
People love to paint Rob as a victim or a villain, but the truth is usually somewhere in the middle. His dating history shows a guy who falls hard and fast. He’s a romantic, but he’s also clearly struggled with self-esteem, which often leads to picking partners that create "chaos" rather than peace.
If you look at the timeline, his "types" have shifted:
- The Sweethearts: Adrienne Bailon, Rihanna (yes, they had a few dates in 2012), and Demi Lovato (rumored).
- The Firecrackers: Rita Ora, Blac Chyna, Alexis Skyy.
- The Quiet Phase: Recent years where he’s prioritized fatherhood over fame.
The Actionable Takeaway
If you’re following Rob’s journey, the real lesson isn't just about who he’s sleeping with. It’s about the importance of personal boundaries. Rob’s most public relationships failed because they were lived out in front of cameras before the foundation was solid.
If you want to stay updated on his status without the clickbait:
- Watch the "behind the scenes": He usually appears in the background of Khloé or Kim’s Instagram stories.
- Ignore the "random model" rumors: Unless a woman is at a Kardashian birthday dinner, it’s probably just a reach for clout.
- Follow Angela White’s socials: She is currently the most reliable source for how Rob is doing emotionally.
Rob Kardashian is currently 38 years old. He’s spent eight years being "serious" about only one girl: his daughter, Dream. Whether a new romance—or an old one—takes center stage in 2026 remains to be seen, but for now, the "Wizard" seems perfectly happy staying out of the line of fire.