Aubrey O'Day has always been a lot. From the moment she stepped onto the screen in Making the Band 3, she was the girl who refused to just sit there and look pretty. She had opinions. She had drive. And, as we’ve seen over the last two decades, she had a very specific, often turbulent way of falling in love.
Honestly, if you look at Aubrey O'Day relationships, they aren’t just a list of names. They’re a roadmap of a woman trying to find "the one" in an industry that’s built on illusions. She doesn't do "casual" well. Everything is a soulmate connection—until it’s a disaster.
The Don Jr. Saga: Not Your Average Affair
If you want to talk about the relationship that shifted the tectonic plates of her public image, you have to talk about Donald Trump Jr.
It started on the set of The Celebrity Apprentice back in 2011. Most people assume it was some tawdry, behind-the-scenes fling, but Aubrey tells a different story. She describes it as a genuine, deep intellectual connection. She’s famously quoted as saying he was her "soulmate" and that he loved her mind more than anything else.
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But there’s the obvious elephant in the room: He was married to Vanessa Trump at the time.
The details are wild. In 2023, she went on Michael Cohen’s podcast and dropped the bombshell that they first had sex in the bathroom of a gay club. Why? Because she was hosting an event there and didn't think he’d actually show up. He did. Suited up and totally chill with the environment.
Why it ended (according to her)
- The Family Pressure: Rumor has it the elder Donald Trump found out and told Don Jr. to shut it down immediately to save the family brand.
- The Transition: Aubrey has been vocal about the fact that she loved the man he almost became. She believes the version of Don Jr. she was with back then—the one who was "enlightened" and "passionate"—died when he leaned fully into the MAGA political machine.
- The Evidence: She basically wrote an entire album about it. Her song "DTJ" and her remix of "Somebody That I Used to Know" aren't exactly subtle. "You said that was the reason for your pain, but you were scared to ruin your family's name." Ouch.
It’s interesting because, even in 2026, people are still dissecting this. Just recently, she mentioned she doesn't think his relationship with Kimberly Guilfoyle is even real. She’s still holding onto the memory of the guy she knew fifteen years ago.
The Pauly D Era: When Reality TV Gets Too Real
Then came the Pauly D years. If the Trump affair was about hidden depth, the relationship with Jersey Shore star Pauly D was about high-octane toxicity. They met on the E! show Famously Single in 2016. It felt like a match made in reality TV heaven—two massive personalities with big hair and bigger egos.
But it was a mess.
They were together for about a year and a half, but they broke up and got back together more times than anyone could count. By the time they filmed Marriage Boot Camp in 2018, the cracks were more like canyons. Aubrey accused him of being "torturous" and controlling. She claimed there were "rules" she had to follow. Pauly, for his part, seemed genuinely baffled by the drama. He famously said he "dodged a bullet" when it was over.
The breaking point? Aubrey reportedly pressured him for a ring way before he was ready. She wanted the wife and kids dream; he wanted to keep DJing and living the bachelor-adjacent life.
The Diddy Factor: Grooming vs. Romance
We can’t talk about Aubrey O'Day relationships without talking about Sean "Diddy" Combs. While they weren't "dating" in the traditional sense, the power dynamic there shaped everything she looked for in men later.
In the 2025 Netflix documentary Sean Combs: The Reckoning, Aubrey laid it all out. She described a pattern of grooming that started when she was just 20 years old. She says she was fired from Danity Kane because she refused to "participate" in the way he wanted.
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She’s been one of the most consistent voices against him for years. Long before the 2024 arrest and the 2025 trials, she was calling him out. She talks about him like a "hurt person who hurts people." The trauma from that era—feeling like she had to be perfect to be loved—is something she’s admitted carried over into her romantic life.
The Lesser-Known Names
It’s not all presidents’ sons and DJs. Aubrey’s history has some deep cuts that people often forget.
- Jesse McCartney: Back in 2008, they were the "it" couple for about five minutes. They were spotted all over New York City, but it fizzled out before it could become anything substantial.
- Pras Michel: She’s confirmed in recent interviews (like on the No Jumper podcast) that she dated the Fugees rapper.
- Travis Barker: There were rumors, but it was mostly just a "moment."
Why We Care So Much
Why do we keep talking about Aubrey O'Day? Because she’s a mirror. She’s the person who wears her heart on her sleeve and then gets mad when people step on it. She moves to Bali to find peace, then flies back to do an interview about her ex. She’s human.
The biggest misconception is that she’s "crazy." Honestly, she just seems like someone who has a very high "soulmate" threshold and a very low tolerance for being ignored.
What can we learn from her journey?
If you're looking for actionable insights from Aubrey’s love life, it's pretty simple: Watch the power balance. Whether it was Diddy or Don Jr., she often found herself in situations where the other person held all the cards—fame, money, or industry power.
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If you're in a relationship where you feel like you're losing your identity just to keep the other person happy, you're in the Aubrey/Pauly zone. And that rarely ends with a wedding.
Next Steps for the Curious:
- Check the Timeline: If you're skeptical about the Trump dates, look at the filming schedule for Celebrity Apprentice Season 5 vs. the release of her 2013 EP Between Two Evils. The lyrics don't lie.
- Watch the 2025 Documentary: For the most recent updates on her legal stance regarding the Bad Boy era, Sean Combs: The Reckoning provides the most factual, witness-backed context.
- Evaluate Your Own "Soulmate" Patterns: Aubrey often mistakes intensity for intimacy. If you find yourself doing the same, it might be time to step back and look at the "rules" of your own relationship.
Aubrey O'Day is currently living a much quieter life in Bali, focusing on healing and, presumably, staying away from reality TV dating shows for a while. But with her, you never know. The next "soulmate" could be just around the corner.