The Unforgettable Love Journey of Ashley Benson: From Cara Delevingne to G-Eazy and Beyond!

Over the years, Ashley Benson has provided insights into her dating life, ranging from long-term relationships to speculation about her costars.

Rising to fame for her portrayal of Hanna Marin in Freeform's series Pretty Little Liars from 2010 to 2017, the actress captivated viewers as her character embarked on a romantic journey with newcomer Caleb Rivers (played by Tyler Blackburn). This on-screen chemistry sparked curiosity among fans, who pondered whether Benson and Blackburn were an item off camera.

The alum from Roswell, NM finally spoke out about the speculation surrounding their relationship once the popular mystery series came to a close. "We were never officially in a romantic relationship. As we navigated our connection as both co-workers and friends, there were moments when the boundaries became blurred," Blackburn revealed during a June 2019 interview with Playboy. "There were times when we had stronger feelings for each other, but ultimately, we are good friends. In general, we found amusement in those rumors. However, there were instances when we wondered if someone had witnessed us hugging. She played a significant role during a pivotal time in my life, so she will always hold a special place in my heart."

Benson garnered attention for her romance with Cara Delevingne between 2018 and 2020. Following their breakup, the California native explained her choice to maintain a level of privacy regarding her personal life.

"I generally prefer to keep my relationships private," she revealed in an interview with Cosmopolitan U.K. in March 2021. "Although being photographed together is unavoidable, I value the sanctity of these moments. They belong to my partner and me, and I believe it is important not to overexpose them. By refraining from exploiting our relationship, we can better safeguard it."

Benson, who was dating G-Eazy at the time, acknowledged the challenges of dealing with public scrutiny of her personal life. She expressed frustration with having to remain silent while others discussed her, highlighting the inaccuracy of judgments made without true knowledge of her. On his end, the rapper shared uncommon glimpses into his connection with Benson prior to their breakup in 2022.

G-Eazy praised his former girlfriend, stating that she is highly skilled in various areas and possesses unique qualities. He expressed his admiration for her acting abilities but was equally impressed by her natural talent for singing, noting her distinct tone and texture. G-Eazy marveled at her hidden talent, which often goes unnoticed by the world. Please continue scrolling to read about Benson's complete dating history.

Credit: Fati Sadou/ABACAPRESS.COM/Shutterstock

Ashley Benson's Dating History: From Cara Delevingne to G-Eazy

From long-term relationships to speculation about her costars, Ashley Benson has offered glimpses at her dating life over the years.

After portraying Hanna Marin in Freeform's series Pretty Little Liars from 2010 to 2017, the actress gained widespread recognition and popularity. Throughout the show, fans witnessed Benson's character develop a romantic relationship with Caleb Rivers (played by Tyler Blackburn), giving rise to rumors of a potential real-life romance between the co-stars. However, the speculation was finally addressed by Blackburn, who shared his thoughts on the matter following the conclusion of the highly successful mystery series.

"We never officially dated, but our relationship as co-workers and friends sometimes blurred the lines," Blackburn shared with Playboy in June 2019. "There were times when we developed deeper feelings for each other, but ultimately we remain close friends. Most of the rumors about us amused us, although there were instances when we questioned if someone had seen us embracing one another. She played a significant role in a major change in my life, and I will always cherish her."

Following their split, Benson gained attention for her relationship with Cara Delevingne, which lasted from 2018 to 2020. Reflecting on her choice to keep her personal life private, the California native explained her decision not to share too much with the public.

"I prefer to keep my relationships private," she shared with Cosmopolitan U.K. in March 2021. "Although there may be instances when we are photographed together, I believe it is more meaningful when those special moments between you and your partner remain sacred. It's crucial to avoid excessive exposure and protect the intimacy of the relationship." During that time, while being linked to G-Eazy, the Her Smell star acknowledged the difficulty of hearing others' opinions about her personal life. "The most frustrating aspect is having to remain silent while others discuss you and navigate through it," Benson expressed. "People are free to say anything about me, but true understanding only comes from truly knowing me."

The rapper provided rare insight into his connection with Benson before their 2022 split, praising her exceptional talent in multiple areas. During an interview with Entertainment Tonight in 2020, G-Eazy spoke highly of collaborating with his then-girlfriend, describing her as a special and talented individual. In addition to her acting abilities, he marveled at her effortless singing skills, noting her unique tone, texture, and innate talent. G-Eazy was amazed by Benson's hidden, special talent that the world doesn't often have the opportunity to witness.

Scroll down for Benson's complete dating history:

Credit: Broadimage/Shutterstock

Ryan Good

The Spring Breakers star went public with Justin Bieber's road manager in 2012. They called it quits after one year of dating but continued to date off and on until 2017.

Credit: Jim Smeal/BEI/Shutterstock

Chord Overstreet

Benson was briefly linked to the Glee alum after they attended the 2012 Teen Choice Awards together.

Credit: Matt Baron/Shutterstock

Tyler Blackburn

After their portrayal of a couple on screen, fans wondered if Blackburn and Benson's on-screen chemistry would translate into a real-life romance. However, the duo quickly dismissed any dating rumors and have maintained a close friendship since wrapping up the popular Freeform series.

Credit: Marksmnan/ Snorlax / MEGA

Cara Delevingne

Benson and Delevingne sparked romance rumors after they were spotted packing on the PDA in 2018. They dated for two years before calling it quits in 2020.  

Credit: Marksman / MEGA

G-Eazy

In 2020, the model ended her relationship with Delevingne and started dating G-Eazy. According to a source, Ashley and G-Eazy are in a committed relationship, although they haven't yet discussed engagement, marriage, or having a baby. The couple is enjoying themselves and their bond has grown stronger during the quarantine.

The twosome were on and off until they officially parted ways two years later.  

Credit: Michael Simon/Shutterstock

Brandon Davis

In February 2023, Benson was spotted accompanying the grandson of Marvin Davis, a prominent oil tycoon, on various public outings. The former Days of Our Lives actress chose to keep quiet about her romantic status until July 2023, when Brandon, her partner, popped the question.