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Ashley Benson dating history: Cara Delevigne's ex flaunts massive ring after engagement to Brandon Davis

The 'Pretty Little Liars' actress is engaged to oil heir fiance Brandon Davis after a string of famous romances
UPDATED JUL 7, 2023
Ashley Benson is engaged to Brandon Davis (Photo by Jon Kopaloff/Getty Images for Max Mara, @ashleybenson/Instagram)
Ashley Benson is engaged to Brandon Davis (Photo by Jon Kopaloff/Getty Images for Max Mara, @ashleybenson/Instagram)

LOS ANGELES, CALIFORNIA: The 'Pretty Little Liars' actress Ashley Benson is engaged to her oil heir fiance Brandon Davis. The 33-year-old actress, who has dated people like rapper G-Eazy and model Cara Delevingne, revealed the news on Instagram by flashing her massive diamond engagement ring. According to her Stories, Brandon, 43, proposed to her after a special supper.

In a post on his Instagram Story, he referred to her as the "love of my life," and Ashley responded, "My best frienddddd I love you." The couple's romantic history began in January, although they had long been friends in the same Hollywood circles.

Who has Ashley Benson dated?

Rumors of a relationship between the 'Pretty Little Liars' actress and the oil heir first surfaced in January 2023 when they were seen watching a basketball game courtside. Long before meeting Benson, Davis, the grandson of oil magnate Marvin Davis, who is worth a billion dollars, was making news. He socialized with Paris Hilton regularly in the middle of the 2000s and had a brief romance with the actress Mischa Barton. However, let's know who Ashley Benson dated before getting hitched.

(@ashleybenson/Instagram)
Rumors of a relationship between the 'Pretty Little Liars' actress and the oil heir first surfaced in January 2023 (@ashleybenson/Instagram)

Justin Thorne


 
 
 
 
 
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A post shared by Justin Thorne (@justinthorneme)


 

Ashley dated musician Justin Thorne of One Call before becoming well-known for her role on 'Pretty Little Liars' in 2009. Ashley even appeared in the music video for the band's song "BlackLight" as Justin's love interest.

Tyler Blackburn

Actors Tyler Blackburn (L) and Ashley Benson attend NYLON and Onitsuka Tiger celebrate the annual May Young Hollywood issue at The Roosevelt Hotel on May 14, 2013 in Hollywood, California.
Actors Tyler Blackburn (L) and Ashley Benson attend NYLON and Onitsuka Tiger celebrate the annual May Young Hollywood issue at The Roosevelt Hotel on May 14, 2013 in Hollywood, California. (Photo by Mike Windle/Getty Images for NYLON Magazine)

On 'Pretty Little Liars', Ashley and Tyler portrayed love interests for Hanna and Caleb, but it was their private connection that got people talking. The two fueled relationship speculations in April 2013 when they were seen holding hands and kissing during Coachella. They have insisted that they are only friends, though. Tyler said, "We never officially dated. In navigating our relationship — as coworkers but also as friends — sometimes the lines blurred a little. We had periods when we felt more for each other, but ultimately we're good buds. For the most part, those rumors made us laugh. But then sometimes we'd be like, 'Did someone see us hugging the other night?' She was a huge part of a huge change in my life, so I'll always hold her dear."

Cara Delevingne

Cara Delevingne and Ashley Benson attend the BOSS fashion show during the Milan Fashion Week Fall/Winter 2020 - 2021 on February 23, 2020 in Milan, Italy.
Cara Delevingne and Ashley Benson attend the BOSS fashion show during the Milan Fashion Week Fall/Winter 2020 - 2021 on February 23, 2020 in Milan, Italy. (Photo by Vittorio Zunino Celotto/Getty Images for Hugo Boss )

When they were spotted kissing at Heathrow airport in London, Ashley and Cara fueled dating speculations. But it wasn't until their first anniversary in June 2019 that Cara formally declared their relationship. They had a private connection, which she briefly discussed in an interview with Marie Claire. Cara spoke of their initial encounter, saying, "We weren't looking for it. It was really just very authentic and natural." However, the pair separated by April 2020, as reported by Popsugar.

G-Eazy

G-Eazy attends GQ Sports Dinner Hosted By DeAndre Hopkins at Brickell City Centre on January 31, 2020 in Miami, Florida.
G-Eazy attends GQ Sports Dinner Hosted By DeAndre Hopkins at Brickell City Centre on January 31, 2020 in Miami, Florida. (Photo by Joe Scarnici/Getty Images for GQ Sports)

After being seen kissing in LA in May 2020, many started to link Ashley and G-Eazy. The two ignited engagement speculations in August 2020 when Ashley was photographed with a diamond ring. Their romance, however, soon ended. E! News announced their breakup in February 2021 after Ashley stopped following G-Eazy on Instagram.

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