Hollywood is weird. One day you’re watching a teen drama queen, and the next, she’s married to an oil heir with a colorful past. Honestly, when news first broke that Brandon Davis and Ashley Benson were a thing, people were skeptical. It felt like one of those random celebrity pairings that wouldn't last a summer.
But here we are in 2026, and they’ve basically become one of the more solid, low-key couples in Los Angeles.
They didn't just date. They moved fast. They got engaged in July 2023, married by November of that same year, and welcomed their daughter, Aspen, on Valentine’s Day in 2024. If you're counting, that's a lot of life milestones packed into about 13 months. Most people take longer to pick a couch.
The Pivot from Party Boy to Family Man
If you grew up in the mid-2000s, you know the name Brandon Davis. He was the "Greasy Bear." He was the guy often seen falling out of clubs with Paris Hilton and getting into very public, very messy feuds with Lindsay Lohan. He was the definition of a Hollywood socialite who had more money than direction.
He’s the grandson of Marvin Davis, the late billionaire who once owned 20th Century Fox and the Beverly Hills Hotel. That kind of legacy comes with a lot of pressure and, apparently, a lot of late nights.
But the Brandon Davis we see with Ashley Benson is... different.
You’ve probably noticed he isn't in the tabloids for the wrong reasons anymore. Since they were first spotted courtside at a Lakers game in January 2023, his "rebrand" has been almost total. He’s transitioned into a music manager and art curator role, leaning more into the family business of entertainment and less into the business of being a "party boy."
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Why the Benson Matchup Surprised Everyone
Ashley Benson has always been a bit of a wildcard in the best way. After seven seasons of Pretty Little Liars, she could have stayed in that "teen star" lane forever. Instead, she took gritty roles in movies like Spring Breakers and kept her private life, well, private. Mostly.
Before Brandon, she had a very high-profile two-year relationship with Cara Delevingne and a stint with rapper G-Eazy. When she started dating Davis, fans were confused. Why him? Why now?
The answer seems to be stability. In interviews, Ashley has been vocal about her desire for a more grounded life. She’s mentioned in the past that she prefers to keep her relationships out of the spotlight because it makes things "too complicated." With Brandon, she seems to have found someone who already lived through the peak of celebrity chaos and is finally over it.
The Timeline of Brandon Davis and Ashley Benson
Sometimes it’s easier to just look at how quickly this happened to understand the "whirlwind" nature of it all.
- January 2023: First spotted together at a basketball game. The internet collectively goes "Wait, what?"
- February 2023: Insiders confirm they are "really into each other." They’re seen on double dates with Emma Roberts.
- July 2023: Brandon posts a photo of a massive oval-cut diamond on Ashley’s finger with the caption "Love of my life."
- October 2023: Reports surface that Ashley is pregnant.
- November 2023: They secretly tie the knot. Her mom, Shannon Benson, basically leaks the news by posting a photo of their gold wedding bands on Instagram.
- February 14, 2024: Baby Aspen is born. A Valentine’s Day baby.
Last year, for their second wedding anniversary in October 2025, Ashley posted a rare look into their life. She shared photos of them in front of the Eiffel Tower and just hanging out as a family. She called him her "best friend" and the "most amazing dad."
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It’s a far cry from the 2006 paparazzi videos of Brandon shouting at reporters.
Dealing With the "Billionaire Heir" Stigma
Let's be real: people judge Brandon Davis because of his family's money. It’s hard not to. When your grandfather had a $6 billion fortune, people assume you’ve never worked a day in your life.
However, the Davis family has also dealt with significant tragedy. Brandon’s brother, Jason Davis, passed away in 2020 from a Fentanyl overdose. His mother, Nancy Davis, has been a public face for Multiple Sclerosis awareness for decades.
This mix of extreme wealth and extreme personal loss usually goes one of two ways: you either spiral or you grow up. By all accounts, Brandon chose the latter once he met Ashley.
They spend a lot of time at Sushi Park in West Hollywood—which is ironically one of the most photographed places for celebrities—but they don't play the "paparazzi game" as much as they used to. They seem content just being parents to Aspen.
What Most People Get Wrong About Them
A common misconception is that this was a "PR relationship." People thought Ashley wanted the "oil money" and Brandon wanted to be relevant again.
But if you look at their 2026 status, that theory falls apart. PR couples don't usually have kids and stay together in the quietest way possible. They’ve managed to do what many Hollywood couples fail at: they stopped caring about the narrative.
Actionable Takeaways from the Benson-Davis Story
Whether you’re a fan or just a casual observer of celebrity culture, there are actually a few "real life" lessons here.
- People can actually change. Brandon Davis is living proof that a "party boy" reputation doesn't have to be a life sentence. If someone wants to settle down, they will.
- Privacy is a choice. Ashley Benson proves that even if you’re famous, you don't have to share every detail of your marriage. Keeping some things for yourself actually helps the relationship survive the "noise."
- Timing is everything. If they had met ten years ago, it probably would have been a disaster. In 2023, they were both ready for something real.
If you're following their journey, the best thing to do is watch for Ashley’s occasional updates on Instagram, as she’s become much more selective about what she shares. You can also look into the Race to Erase MS gala, which Brandon’s family hosts annually; it’s usually the one time a year they make a formal, "official" public appearance together for a cause that matters to their family.