Ashley Benson Dating Timeline, Relationship History, Ex-Boyfriends


Unlike her Pretty Little Liars co-stars, Ashley Benson has pretty much fallen off the radar ever since the drama came to an end in summer 2017. That’s why when she recently made headlines for a new relationship, we were, like, NO. WAY.

Before we get into the nitty-gritty details of her latest foray into coupledom, let’s talk about all the celebrities the 28-year-old PLL alum dated ever since she entered the entertainment industry. After all that, then we’ll discuss her latest relationship. And, let us tell ya, it’s a juicy one!

Justin Thorne

Ash dated singer Justin Thorne before she shot to superstardom. She even appeared in his band’s music video for “Blacklight!”

Chord Overstreet

After Chord Overstreet and Emma Roberts broke up, he and Ashley were spotted out and about together multiple times. The two never fully confirmed if their relationship was anything other than casual, however… but, at the very least, we know there was a hookup.

Taylor Lautner

Ashley and Taylor Lautner were spotted having a romantic dinner in 2012 at LA’s hot Mexican restaurant, Red O. They sat far back in the corner of the restaurant and apparently looked smitten! Three years later, they were once again rumored to be dating after appearing in several social media posts together. Again, no confirmation was given.

Tyler Blackburn

Ashley and Tyler Blackburn have always denied being anything other than BFFs, but it seemed like the two were constantly canoodling during their time as PLL co-stars. From holding hands to sneaking kisses, we’re not sure if they really do just have a super close friendship or if they were ever romantic partners.

Keegan Allen

Many people assumed these on-screen co-stars were more than friends due to their close relationship and even closer Instagram pics they constantly posted. Keegan Allen, we’re on to you…

James Franco

The Spring Breakers co-stars always downplayed their rumored relationship, but Ash & James Franco definitely did look cozy together more than once following their on-screen makeout sesh with Vanessa Hudgens.

Nat Wolff

Ash was spotted holding hands with fellow actor Nat Wolff in October 2015. The two looked to be enjoying each other’s company as they took a late-night stroll through NYC. Hmm…

Ryan Good

Ashley first started dating Justin Bieber‘s swag coach in 2011, and they were on-again, off-again for years. The last time they appeared to be “on” was in November 2017, when they attended a hockey game together.

Cara Delevingne

The Internet exploded when pictures of Ashley and Cara Delevingne making out at Heathrow Airport came out in August 2018. Considering Ash had only (publicly) dated guys in the past, it was pretty shocking. But it turns out she and Cara had actually been dating for a few months prior to the pics! We ship it.

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