Cara Delevingne’s Dating History Includes a Mix of Actors and Musicians: Ashley Benson, St. Vincent, More

Jake Bugg

Cara and the British musician, who were introduced by mutual friend Rita Ora, dated in 2013. At the time, both of their careers were taking off and as a result, they split to focus on work.

Miley Cyrus

In 2013, Miley posted a photo of her and Cara licking each other’s tongues. At the time, the pop star was on a break from her on-again, off-again man, Liam Hemsworth, so it’s possible the two were briefly more than friends, though neither party confirmed the rumors.

Harry Styles

As it was! It was rumored that the singer and model were dating in the summer of 2013. However, neither of them addressed their possible romance.

Cara cat walking her way through Spring 2014 fashion shows and Harry was spotted front and center, cheering on the Paper Towns star. 

Michelle Rodriguez

The following year, Cara began dating the Fast and Furious actress. By the looks of it, the duo had a blast during their short-lived romance.

“It’s going really well,” Michelle told The Mirror six weeks after they began dating. “She’s so cool. When we started hanging out I just thought she was awesome, and we have the best time together. She’s hard though. You wouldn’t want to mess with her in a fight.” After six months together, they broke up.

St. Vincent

Prior to dating Ashley, Cara’s relationship with St. Vincent seemed to have been her most serious. The two were together from 2015 to 2016 and were head over heels for each other.

“I’m completely in love … Before, I didn’t know what love was – real love,” Cara revealed to British Vogue in 2016. “I didn’t understand the depth of it. I always used to think it was you against the world. Now I know the meaning of life is love. Whether that’s for yourself or for the world or your partner.”

The former flames split after a year and a half of dating but fortunately ended on good terms.

Ashley Benson

Cara became romantically linked to the Spring Breakers star in 2018. At first, the pair were keen on remaining low-key, but as their relationship progressed, they began sharing photos of each other getting cozy.

Their bond was so strong, Cara even admitted she had never been truly vulnerable with someone before Ashley. “I’d never truly let anyone in before, for fear of them leaving,” she divulged to Porter in September 2019. “I never really trusted people or felt worthy of it, and I always pushed them away. She’s the first person that has said: ‘You can’t push me away. I’m going to be nice to you, I love you.’ I’m just like, ‘Wait, so all I have to do is just let you be nice to me? Why have I never done that before?'”

They split in April 2020.

Jaden Smith

The pair were spotted spending Valentine’s Day together at a Los Angeles restaurant in February 2021. It didn’t appear to be a friend-zone date as Jaden welcomed her with roses and a sweet kiss.

Sienna Miller

Cara and her best friend were reportedly spotted “making out” at Temple Bar in New York City in January 2022.

According to Page Six, Cara, Sienna and their pals took over a corner table at the cocktail lounge. An insider divulged that it looked like they “were together,” though the actress also made out with a guy at their table.

“It was like fluid friends. Sienna made out with this tall guy, and then she made out with Cara,” the source told the outlet, noting that Cara’s sister Poppy was also there. “It was like a fun night out.”

Cara and Sienna’s reps did not immediately respond to Life & Style‘s requests for comment.

Leah Mason a.k.a. Minke

The lovely couple was first spotted making out in Portofino, Italy, in June 2022, according to photos obtained by Page Six.

Although they keep their romance private, Cara shared her Valentine’s Day plans with Minke during a February 2023 appearance on The Kelly Clarkson Show.

“Sometimes I’ll do a ‘Galentines Day.’ [This year] I’ll probably be spending it at home with my dogs and my girlfriend – Very low-key,” she said at the time.