Red Flags In Presley Gerber's Dating History

Presley Gerber's life has hardly been free from controversy. As the son of iconic supermodel Cindy Crawford and businessman (and former model) Rande Gerber, he's a classic case of the nepo baby, having appeared in a Pepsi commercial alongside his mom as young as a toddler. After taking the most obvious cue from his parents and delving into the modeling industry himself, Presley has publicly claimed to have always felt "misunderstood," even famously tattooing the word on his face despite massive concern from fans. His parents felt the drastic move may have been a cry for help and one of the tragic moments in his life, and he ultimately had the tattoo removed.

While Kaia Gerber, Presley's famous sister, has happily followed in their mother's footsteps, telling People in 2023, "I won't deny the privilege that I have," he's seemingly taken the path of rebellion. "Presley is obviously going through a super rebellious phase right now. He is trying to get out of the shadow of his family and find his own way and create his own identity," an insider revealed to Us Weekly back in 2020. "Presley feels like there's a lot of pressure on him because his parents and Kaia are so successful, and Kaia is thought of as a 'sweetheart' and Cindy and Rande have such respected reputations in everything they do. He wants to do his own thing and find his own place in the world."

With a habit of flipping the bird to the paparazzi and a DUI under his belt by age 19, it's safe to say that Presley has struggled with being in the public eye, so it's unsurprising his dating history has its fair share of red flags. Read on to learn all about who the model has been linked to, and all of his most cringe-worthy romance-related moments.

Move over Adam Levine and Leonardo DiCaprio — we have another model-only dating novice on the scene. Being a modelizer, or someone who only dates or associates with models, is largely considered to be a huge red flag, and despite publicly expressing his dislike for the modeling industry, Presley Gerber only seems to be interested in women who are a part of it. As the only son of supermodel Cindy Crawford has grown up to be gorgeous, one could argue he's simply running in his own circle as a model himself, but out of the handful of women he's been linked to (we found seven) every single one of them counts posing for the camera as part of their career. 

While he's most recently in a relationship with Instagram-famous Isabella Jones, Gerber began his public dating history with up-and-comer Cayley King in 2017, who was famously compared to his mother. After quickly moving on to Canadian model Charlotte D'Alessio, who he dated for the better part of 2018, he dated Los Angeles, California native Cameron Rorrison from 2018 to 2020. Gerber has also been linked to model Sydney Brooke and English model Hana Cross, and he was rumored to be engaged to model and influencer Lexi Wood in 2022. That's a lot of models, and it makes us wonder if being one is an official prerequisite to getting on Gerber's dating card.

Things were getting romantic on Presley Gerber's Instagram page in November 2022, when he announced that things were official with model and influencer Lexi Wood. The deluge of photos and videos of them getting hot and heavy (featuring Gerber grabbing Wood's butt and the two embracing and kissing) have since been deleted, but at the time it was clear the couple wanted the world to know about their love. A caption on one of Gerber's carousels ramped up the rumors of their potential engagement: "Guys I did it..." Gerber penned, alongside red heart and infinity emojis. 

The Canadian model was linked to another famous nepo baby back in 2018, Brooklyn Beckham, whose parents you may recognize as Victoria Beckham from the '90s pop group the Spice Girls and soccer superstar David Beckham. It's clear that Wood had entertainment industry aspirations of her own, and an insider for E! News soon implied that Wood wanted to focus only on herself, rather than on a future with Gerber. "They realized very quickly it wasn't going to be a long-term relationship," the source said.

There seemed to be bad blood between the two when it came to the breakup, with Woods posting a brutal quote to her Instagram story on December 9, just one month after she publicly declared her love for Gerber. "She moved on and I feel story for you, because she overlooked your flaws, your temper, your selfishness, your inability to love anyone but yourself... Maybe she will now fight for someone who loves her, instead of someone who sucks the life out of her, never satisfied, even with her beating heart in his greedy hands." (via E! News) Ouch.

Presley Gerber and Isabella Jones, known to her Instagram followers as Bananablue17, sparked dating rumors in early 2024 and have since gone full social media official. Jones posted a poolside shot of Gerber on her Instagram story with the caption "my love @presleygerber" in June of 2024, but he finally made the grid on July 2, 2024, when she made a gushy post for the model's birthday. A carousel of photos and videos of the couple together accompanied by the caption "happy birthday baby! i love you so much my everything" left no doubt in anyone's mind regarding the status of their relationship. Gerber returned the gesture in a matter of weeks, expressing his love for Jones on her birthday a mere 18 days later. "Happy birthday baby!!! I love you so much. You have changed my life in all the best ways," he captioned a carousel of his own.

Typically there's nothing controversial about a couple expressing their love for each other on their socials, but fans have taken issue with this relationship for a very specific reason — Jones used to be besties with Charlotte D'Alessio, who dated Gerber from 2017 to 2018. The former friends no longer follow each other on Instagram, and the alleged betrayal of girl code has fans reeling in Jones' comments. "Wasn't he charlottes ex and you charlottes best friends ???" a top comment reads on Jones' birthday post for Gerber. Another commenter weighed in on a carousel of the couple that Jones posted in August of 2024, saying "dating @charlottedalessio's ex is crazy and him dating all of his sisters friends is bizarre."

Speaking of Presley Gerber's ex-girlfriend Charlotte D'Alessio, they were introduced by his famous sister Kaia Gerber. It's no secret that both of Cindy Crawford's kids lead lavish lives, and Kaia counts many of the fresh-faced models in the industry today as close friends. It seems her brother has met more than one of his love interests through her, and we can't help but wonder how awkward things get for Kaia when things ultimately don't work out between her brother and her friends.

For example, D'Alessio is known for being discovered at Coachella, with a single picture catapulting her Instagram following into the hundreds of thousands virtually overnight. She soon signed with Wilhelmina and later Elite, making her an eligible choice for modelizer, Presley. D'Alessio's predecessor, Cayley King, who Harper's Bazaar called a "supermodel in the making," is a known friend of the family — Kaia in particular. She dated Presley in 2017.

Even more bizarre than dating his sister's friends, was the time Presley stepped out with an unknown woman who bore a haunting resemblance to Kaia, herself. He was spotted on a date with the girl in question in Malibu, California, in September 2022. Presley still has time to outgrow his fixation on models who have more in common with his sister than they do with him, but we aren't going to hold our breath.