Ashley Benson Went From Dating Cara Delevingne to Getting Engaged to This Wealthy Man

Kelly Corbett - Author

Oct. 16 2023, Updated 3:06 p.m. ET

Ashley Benson and her exes
Source: Getty Images

The Gist:

  • Ashley Benson dated Cara Delevingne for nearly two years before the two split up.
  • Ashley's longest relationship to date was with Ryan Good. They dated for nearly five years.
  • In July 2023, Ashley got engaged to Brandon Davis.
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Over the years, Pretty Little Liars alum Ashley Benson has dated a handful of famous celebrities. And in January 2022, we learned that she got back together with one of her exes, rapper G-Eazy, although that fizzled out.

The pair was first linked to each other in May 2020 but were said to have broken things off in February 2021. However, we later learned that they reconnected and briefly dated in 2022. Following that relationship, Ashley met someone new and things have gotten quite serious. Keep reading to get the scoop on Ashley's current partner and find out more about her past romances.

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Ashley Benson arrives at the Los Angeles Premiere Of Max Original Limited Series 'Love & Death.'
Source: Getty Images

Ashley began dating Ryan Good in 2011.

Ashley's earliest known boyfriend was a guy named Ryan Good. Per Teen Vogue, he was allegedly Justin Bieber's onetime swagger coach. Ashley gushed over him to the outlet in 2012, noting that at the time they had been dating for over a year.

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"The first couple of months, it was all Skype," she said, adding, "He was in Japan, Europe — everywhere. I'd have to wake up at 2 in the morning to talk to him. It's hard being in this industry. You're always away from your family and friends and boyfriend."

Ryan Good (L) and actor Ashley Benson attend The Comedy Central Roast of Justin Bieber.
Source: Getty Images
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Sadly, in a 2013 interview with Seventeen, Ashley revealed that she and Ryan had broken up. However, rumors swirled that they continued to date on and off until 2016.

Did Ashley Benson actually date Tyler Blackburn?

Ashley was also rumored to have been dating her PLL costar Tyler Blackburn, who played her love interest on the show, for years. During a June 2019 interview with Playboy, Tyler finally spoke about his relationship with Ashley. He confirmed that they were never boyfriend and girlfriend, although he did hint that they may have had feelings for one another.

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Ashley Benson and Tyler Blackburn in white t-shirts.
Source: Getty Images

“We never officially dated,” he shared. “In navigating our relationship — as co-workers 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," he said.

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Cara Delevingne and Ashley Benson were together for nearly two years.

Cara and Ashley sparked dating rumors in May 2018 after a fan claimed that they saw the pair making out at an SNL special. Ashley was the first to confirm their relationship over an Instagram comment in September of that year. However, the following day she claimed she was hacked and those weren't her words.

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Regardless, the two were said to have been together for two years until May 2020. But during that time, their relationship stirred up a lot of chatter about their sexuality. While Cara told W magazine that she considers herself "fluid" and has no preference between men or women, Ashley never openly commented on her sexuality. Back in 2015, however, she did share her thoughts on dating with FASHION.

Ashley Benson and Cara Delevingne sitting together at an event.
Source: Getty Images
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"Relationships are so hard in this business, she told the outlet. "It's too much attention when two powerful people are together. Everything is heightened and exaggerated. The strangest thing that I've read is that I've dated all the male co-stars I've had on Pretty Little Liars. None of it is true. It's disgusting," she continued.

What's the scoop on Ashley Benson's relationship with G-Eazy?

Following her split from Cara, Ashley was seen locking lips with G-Eazy that same month. The duo had met after collaborating together on a cover of Radiohead's "Creep," which he posted to his YouTube page in April 2020.

Because of how recently Ashley and Cara had ended things, some fans claimed that Ashley left Cara for G-Eazy. However, it's unknown if there is any truth to that.

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G-Eazy in a green outfit and Ashley Benson in a white formal outfit.
Source: Getty Images

Ashley and G-Eazy split up in February 2021. However, a source confirmed to Us Weekly in January 2022 that the exes had reconciled and were back together.

“They’re together. They just like to keep their relationship private,” the source told the outlet, adding that Ashley and G-Eazy “never lost touch” after they had broken up. “They know no matter what, they have each other to lean on during tough times," the source added.

Despite their connection, it's clear Ashley has clearly moved on.

Ashley Benson and Brandon Davis were romantically linked in January 2023.

After word broke that Ashley was dating Brandon Davis in January 2023, the grandson to the late oil tycoon Marvin H. Davis, things have only gotten more serious. In July, Ashley announced via Instagram that she and Brandon were engaged! A few months after that we're finding out the PLL alum is pregnant. Now, the only thing left for this couple to do is to say "I do," though some fans are now speculating they might have already done that in private. Only time will tell!

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