Ashley Benson’s Dating History: From Cara Delevigne to Husband Brandon Davis

It’s no pretty little lie that Ashley Benson has known love. Meet the men and woman who have captured her heart through the years.

• Ashley Benson is an actress, perhaps best known for her role as Hanna Marin in the teen drama series Pretty Little Liars.
• She’s had several high-profile relationships, including with model Cara Delevingne and musician G-Eazy.
• In 2023, she married Brandon Davis.

Ashley Benson married Brandon Davis after he popped the question with a giant oval engagement ring this past July. The exciting news — which was reported on November 8 —  comes less than a year after the two were first spotted together in January 2023. However, this is far from Ashley’s first relationship in the public eye. She’s dated plenty of familiar faces over the years, including Cara Delevingne and G-Eazy.

The Pretty Little Liars star isn’t one to open up about her personal life much, though, and it’s a conscious decision. “I usually keep my relationships private,” she said in a 2021 interview with Cosmopolitan U.K. “You obviously can’t help if you get photographed together. [But] it’s more sacred that way. Those private moments are for you and your partner and I think it’s best not to be over-exposed. You can really protect your relationship if you’re not exploiting it.”

Learn more about Ashley’s love life and what we know about her romances — both past and present — below:

Brandon Davis

Ashley and Brandon first sparked romance rumors when they were photographed attending a basketball game together in January 2023. It’s unclear how long they were seeing each other before they went public, but by February 2023, PEOPLE had confirmed the relationship. “They have a lot of mutual friends and are both super fun and very social people,” the mag’s source revealed.

On July 6, 2023, Ashley confirmed via her Instagram Storoes that she and Brandon had gotten engaged. She shared the news by posting a close-up photo of her gorgeous engagement ring, which featured an oval diamond on a simple, gold band. The two reportedly got married in November 2023, and she is pregnant with their first child.

Brandon is an heir to oil tycoon, Marvin Davis, who is his grandfather. He has four siblings, although one died in 2020 from a Fentanyl overdose at the age of 35. Brandon was known for partying with stars like Paris Hilton and Mischa Barton, who he briefly dated, in the early 2000s. He also publicly shamed Lindsay Lohan during a night out with Paris, infamously calling her a “fire c*****” in front of paparazzi.

G-Eazy

Before getting together romantically, Ashley and G-Eazy collaborated on a cover of “Creep” by Radiohead in April 2021. Just weeks later, following Ashley’s breakup from Cara Delevingne, the two were photographed out in Los Angeles together. At the time, though, Us Weekly reported that their relationship was “not serious,” but they were “hanging out.”

Subsequent sightings followed, and the two appeared to get more serious by June, as Ashley brought G-Eazy as her date to her sister’s very intimate wedding. Ashley was also featured on a song on G-Eazy’s June 2020 project, Everything’s Strange Here. By August, the actress was photographed wearing a diamond ring on her left hand, sparking engagement rumors. However, it was never confirmed whether the two had actually gotten engaged.

“She’s an exceptionally talented person in many different spaces,” G-Eazy gushed to Entertainment Tonight in Oct. 2020. “She’s a special one. Obviously, she’s a great actress, but, you know, getting to work with her and putting her in front of a microphone and watching her sing so effortlessly….it just blew me away that you can have such a hidden, special talent that the world doesn’t get to see as often.” In her own interview with Cosmopolitan U.K., Ashley gushed about how much G-Eazy was “teaching” her about music, and said it was “really nice” to write songs with him in quarantine.

Although a source told Us Weekly in Jan. 2021 that Ashley and G-Eazy were very serious and “in a great place,” they called it quits by February of that year. “[Ashley] felt he hadn’t been fully committed to her,” a source told E! News about the breakup.

Still, they spent time together following the split, even though they were reportedly not “back together” romantically. After months apart, though, Ashley and G-Eazy found their way back to each other. Page Six obtained photos of them together in Dec. 2021, and by January, reports claimed that they were fully an item again.

At a pre-Oscars party in March 2022, the on-again couple packed on the PDA and reportedly did not care who was watching. “They looked very much in love and did not leave each other’s side,” Page Six reported. The rekindled romance didn’t last, though, and Ashley and G-Eazy broke up again before the end of the year.

Cara Delevingne

Ashley and Cara were in a very publicized relationship for two years from 2018-2020. The ladies both starred in the 2018 film Her Smell, and were first linked when they were photographed kissing at Heathrow Airport in London that August. Their romantic relationship was confirmed by US Weekly in October 2018, with a source confirming that it was Ashley’s first relationship with a woman.

For the first several months of their relationship, Ashley and Cara kept quiet about their love for one another, even as they were photographed out and about on various occasions. By June 2019, Ashley had moved into Cara’s home after selling her own place. Cara made a big statement about their relationship that month for PRIDE, as well, when posted a video of herself and Ashley kissing on Instagram. The timing came right around the ladies’ one year anniversary, as well.

Ashley was also Cara’s date to the TrevorLIVE Gala that month, and Cara did not hold back from gushing about her girlfriend. “She is one of the people that helped me love myself when I needed it most and I really needed it,” Cara said. “She showed me what real love is and showed me how to accept it, which was a lot harder than I thought.”

At the end of 2019, Cara sparked concern when she tweeted, “Me and Ashely broke up.” However, it turned out that her account had been hacked. She proved they were still together with a gushing birthday post for Ashley on Instagram that December. “There is so much I could say but something I love and cherish most about us is that I don’t need to because YOU KNOW and that’s all that matters,” Cara shared. “It’s you and me, which is my favorite. My save place. You let me be silly, you let me be wild, you keep me free, secure and curious. I feel like I’ve known you my entire life and I am so proud of watching you grow into the woman that you always dreamt of being.”

The gals were still going strong on Valentine’s Day, and proved it with their respective social media posts for each other that year. However, by the beginning of May 2020, they had split. Although the ladies never publicly delved into the reasoning for the split, Cara hinted that the COVID-19 pandemic took a toll on their relationship. “It was the most trying time,” she admitted to Cosmopolitan. “It really makes or breaks you.”

Chord Overstreet

Ashley and Chord Overstreet were briefly linked during the summer of 2012. The two turned heads when they attended the Teen Choice Awards together in July of that year. Days later, they were photographed having a late night out at hotspot Bootsy Bellows. The summer romance continued into September, as they also attended a pool party in Las Vegas together for Labor Day weekend. However, things eventually fizzled out between the two, and little is known about the status of their actual relationship at the time.

Tyler Blackburn

Tyler Blackburn played Ashley’s love interest on Pretty Little Liars, and their close friendship IRL had fans constantly speculating if they were also dating off-screen. Once the show ended, Tyler shut down rumors of a romance when he spoke to Playboy in June 2019, but he did say that sometimes the lines were “blurred” when it came to the pair’s real life relationship.

“We never officially dated,” he insisted. “In navigating our relationship — as co-workers, but also as friends — sometimes the lines blurred a little. We had periods where 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.” Since Pretty Little Liars concluded, Ashley and Tyler have remained friends.

Ryan Good

Ashley and Ryan dated on and off from 2012 until 2017. At the height of their relationship, Ryan was close friends with Justin Bieber, working as his road manager during the early years of his career. Ryan is now the creative director of Justin’s clothing brand, Drew House. He also subbed in as Justin’s stylist in the early days. Because of Ryan and Justin’s close friendship, Ashley also spent a lot of time with the Biebs, as well as his on/off girlfriend, Selena Gomez (she also starred in Spring Breakers with Selena in 2013).

When Ashley and Ryan split for the first time in 2013, she opened up to Seventeen about being single. “Anytime you go through a breakup, it’s rough,” she admitted. “Ryan and I are still close, but I’m too young to be in a serious relationship. Work is my boyfriend!” By December of that year, they were fully back on, though, and were seen on vacation together in 2014, as well. They continued to breakup and get back together before calling it quits for good in 2017.