Explore Ashley Benson's Dating History As the Actress Reveals First Pregnancy

Actress Ashley Benson is expecting her first baby: Dive into the Pretty Little Liars star's dating history!  

Ashley Benson, who famously portrayed the snobby Hanna Marin in the teen mystery-drama series, Pretty Little Liars, was a huge part of our teenage years. Since the show ended after seven successful seasons in 2017, Benson has kept her onscreen presence consistent. The Teen Choice Award winner has starred in hit flicks like The Birthday Cake, Her Smell, and more.   

Born on December 18, 1989, in Anaheim Hills, California, Benson's career in the entertainment industry became apparent in her early years as she started showing innate flair and interest in dancing and singing. At 15, Benson landed a recurring role in Days of Our Lives and also made her big-screen debut in 13 Going on 30. The 33-year-old actress recently shared that she is soon to be a first-time mom.  

Ashley Benson's Complete Dating History!  

In navigating her stellar career, Benson has shown the utmost versatility and escaped being pigeonholed to similar roles. The actress's love life is no different. Ashley's dating history barely shows a repetitive pattern or a desired type. From athlete, co-star, rapper, and even woman, Benson has tried them all.   

Benson may boast one of the most interesting dating history but the Pretty Little Liars alum certainly believes in keeping it private as possible. That way, she states, the relationship remains more sacred. Ashley's earliest relationship experience goes back to 2012 when she started dating Ryan Good, Justin Bieber's road manager at the time.  

Just like their close acquaintances, Bieber and Selena Gomez's on-and-off romance during those years, Benson and Good continued to have an on-off romance until their final split in 2017. Of course, Benson dated and was linked to other people when she and Good were on a break.   

In the summer of 2012, Ashley was rumored to be dating Glee actor Chord Overstreet. And while starring in Pretty Little Liars, Ashley's close friendship with her co-star, Tyler Blackburn, who played her love interest on the show, had fans guessing if the duo had translated the onscreen romance into real life.  

The truth about their long-speculated relationship was only revealed after the show ended. Blackburn shared that though the two never gave the relationship a shot, there were times when the lines were blurred. "We had periods where we felt more for each other,  but ultimately, we're good buds," Blackburn explained.   

Ashley's most shocking and unlikely relationship was with English model Cara Delevingne, whom she dated for two years. The pair first sparked dating rumors when the two were spotted packing on PDA in 2018. The pair's frequent posts of each other and an apparent effort to give it back to prying paparazzi soon made them one of the favorite queer celeb couples.    

"Cara and Ashley always had their ups and downs before but it's over now," a rep said while revealing their breakup in April 2020, adding, "Their relationship just ran its course." Following her high-profile split from Delevingne, Ashley famously dated rapper G-Eazy.  

Benson, 33, who previously dabbled in music, collaborated with G-Eazy on a cover of Creep and discovered something more in their relationship. A source explained how the two had turned very serious within a month of dating. Although the pair's romance lasted two years, they were on and off during the period.  

Ashley Benson is Expecting Her First Baby with Brandon Davis!   

Ashley is looking forward to the most exciting and rewarding chapters of her life. Not long ago, the Pretty Little Liars actress sent her fans and the media into a frenzy when she announced that she had gotten engaged to Brandon Davis, whom she started dating earlier this year.   

While many thought the step was a hasty decision given the duo's brief relationship, a section wished the duo well. While flaunting her massive oval-cut diamond engagement ring, Ashley called Davis "the love of my life." Either the pair are madly in love or it is one quick-paced decision after another because the couple is now expecting a baby.    

Benson and Davis are reportedly expecting their firstborn!

"I don't know how far along she is, but she has been showing since at least September," an insider while sharing the joyful news. The close source further adds, "Her inner circle already knows, but I'm not sure she will say anything publicly until the baby is born. Benson's soon-to-be husband, Davis, is the grandson of Marvin Davis, a billionaire oil tycoon.   

Davis was known for being a close acquaintance of socialite Paris Hilton in the mid-2000s. The oil heir was in a relationship with actress Mischa Barton in the early 2000s. "They have a lot of mutual friends and are both super fun and very social people," a source as they explained the duo's relationship dynamic.  

Stay connected to Married Celeb for more.