Cara Delevingne and Ashley Benson Breakup Timeline

May 2024 · 4 minute read

The day Ashley Benson and Cara Delevigne broke up after two years together was the day I began to question everything.

At the time, I was in a relatively new queer relationship — my first — and drawing strength from Benson’s confidence as an out and proud woman in one of the hottest coupledoms in Hollywood. And when she and Delevingne split, and the 30-year-old moved on with G-Eazy, I wondered if I, too, would one day fall back into the arms of men. After the internal struggle to embrace my sexuality, I knew I didn’t want that for myself. But also, there was a part of me that wondered if it was inevitable.

Millions of lesbians took to the internet to mourn Benson and Delevingne’s relationship when they announced their split in May of this year, begrudging that even the best of us can fall susceptible to the spell of a mediocre tall guy with tragic tattoos. Sexuality is fluid, the binary is a construct, and queerness is not dictated or diminished by who you love, but I still worry that if Benson left Delevigne for G-Eazy, what’s stopping me from leaving my girlfriend for a(nother) SoundCloud rapper?

My girlfriend and I are a new thing, a heartbeat pulsing like ellipses that appear when she texts back. We convince each other we aren’t obsessive, but text “I miss you” the second the other is home, wondering how long the distance between us will last this week. There’s nothing to worry about when you’re five months in, when the fireworks still spark and cat names are debated in restaurants. Still, doubt underlies my first lesbian relationship — how couldn’t it, given the blips in my past that were men?

I grew up on the Pretty Little Liars franchise, both the books and the show. I watched episodes weekly with my boyfriend at the time, who was, surprise, a white rapper. He felt a gravitational pull to Benson, he told me, which I believed was because he was attracted to her more than he was to me. Whether I wanted to be her or be with her was always the question, but the answer was solidified when I saw her running around in a pink bikini in Harmony Korine’s Spring Breakers. She was hot, confident, and most importantly, fearless. She was everything I wanted to be and everything my boyfriend wanted me to be, as well.

The Benson/Delevigne timeline began on the set of Her Smell in 2018 and was confirmed June, 2019. The public tiptoed with them as they dove into a relationship concealed behind closed doors, the kind where straight people wonder if women are “really gay” or just “make out at a party drunk gay.” Benson radiated in her first public lesbian relationship, dressing to the ten’s and getting her partners initials tattooed on her rib cage. Delevingne gushed about her in public. For me, this was the push I needed to fully explore my queerness alongside a childhood idol. I wanted to embrace what Benson embraced two years prior, but never had the courage to let go and give in to love that was liberating — until finally, I did.

I met Ana shortly before the Benson and Delevigne breakup and watched us unfold as they diminished, the Pretty Little Liars star downgrading (in my personal opinion) to a rapper who’s a five, at best. We exchanged kisses, then exchanged articles on who would get Benson and Delevigne’s infamous “sex chair.” Benson laid out a dynasty I would build upon, with my own smoking hot girlfriend I will also one day buy a sex chair with.

Her journey precedes mine — a map I used to reference for my own path forward. But now that map is lost; it belongs to her, not to me. I’ll never backslide into who I was when I dated a white rapper and watched trash television with him on a futon in college, but I still watch trash television. I still own a futon. How do I know I won’t fall into everything I knew before I was gay? Before I saw Benson kissing G-Eazy in People Magazine? Seeing a cis-het relationship will never diminish what I know, but it does spark fear. How do I know I won’t return to the same slimy lips I set mine upon when I was 19?

I guess it’s time to begin drawing my own map.

Breakups That Broke Us is a weekly column about the failed celebrity relationships that convinced us love is dead.

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