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All of Pete Davidson’s Girlfriends in Chronological Order

By Kratagya Rathore
22 Oct 2023
All of Pete Davidson’s Girlfriends in Chronological Order
Lifestyle
All of Pete Davidson’s Girlfriends in Chronological Order

Love him, hate him or laugh with him, Pete Davidson is a true-blue charmer, a lady’s man if we may say so. The charismatic comedian from Saturday Night Live has not only left us in splits with his humourous antics but also kept us glued to our phone screens with all the news about his fascinating love life. In the past half-decade, this ‘bad boy’ of comedy has established himself as pop culture’s ‘It boy’, thanks to his uncanny ability to charm his way into the hearts of some of Hollywood’s most glamorous women.

From his whirlwind romance with mega-celebrity Kim Kardashian to the headline-grabbing breakup with songstress Ariana Grande, Pete Davidson’s list of girlfriends and dating history reads like a script plucked from a rom-com. 

Social media is constantly abuzz with chatter about his romantic escapades and with good reason. After all, the comedian has had as many as 12 girlfriends and it’s become somewhat of a pop culture trend to make predictions about which A-lister he’ll be dating next. Davidson, who is just 29 years old, has had a dating spree so extensive that it’s like he’s on a mission to date a new girl every year. Perhaps, Ariana Grande was right when she tweeted about Pete’s ‘big dick energy’ back in 2018!

Now, with rumours swirling about a budding romance between Pete and actress Madelyn Cline, it’s the perfect time to deconstruct Pete Davidson’s dating history. 

Pete Davidson’s girlfriends and dating history 

pete davidson girlfriends
Picture Credits: Instagram/Saturday Night Live

From girlfriends to flings and beyond, we are unravelling the list of Pete Davidson’s girlfriends. Check it out. 

Carly Aquilino: 2015 – 2016

The chronicles of Pete Davidson’s wild love life began in 2015 with comedian and actress Carly Aquilino. A familiar face from the comedy series Girl Code, Aquilino was more than just Pete’s first girlfriend. The two also bonded over their shared love for comedy.

Their romance kicked off in 2015, nearly eight years ago, marking the start of Pete’s public love life. However, like many young love stories, it had its ups and downs and by 2016, the romantic entanglement had come to an end.

Cazzie David: 2016 – 2018

 

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A post shared by Cazzie David (@cazziedavid)

Following his break-up with Aquilino, Pete found himself entangled in another comedy connection, this time with Cazzie David, the daughter of legendary comedian and Curb Your Enthusiasm creator Larry David. 

The lovebirds were going strong and even moved in together in May 2016. However, their relationship didn’t last for long and by 2018, Pete and Cazzie decided to go their separate ways. The breakup didn’t spell the end of their connection entirely. In true Pete Davidson style, the two managed to rekindle their friendship, proving that sometimes exes can stay friends.

Ariana Grande: (2018)

Next up on the list of Pete Davidson’s girlfriends is pop sensation Ariana Grande. Their relationship was pretty high-profile, with sparks flying from their first kiss at the 2018 Met Gala on May 7. This iconic moment ignited a romance that would go down in history, not just for their red-carpet debut but also for a cheeky Twitter exchange that had the world talking.

Picture Credits: X (formerly Twitter)

Ariana’s not-so-subtle tweet in response to a fan’s curious question about Pete’s ‘size’ became an internet sensation. It was a hilarious, wink-wink moment that allegedly revealed Pete’s ‘big secret’ with a dash of humour. 

The two even got engaged in June 2018 but their romance was short-lived, with the couple parting ways in October 2018, citing that it was all “too much too soon.”

But, hey, it wasn’t all in vain. The breakup inspired Ariana to release the hit song Thank U, Next, which quickly became an anthem of empowerment for women. As for Pete, he covered up his neck tattoo inspired by Ariana, a clear sign of moving on.

Kate Beckinsale: (2019)

In the aftermath of his romance with Ariana Grande, Pete didn’t waste any time in finding a new girlfriend. He turned heads and raised eyebrows when he got together with British actress Kate Beckinsale, another iconic name in the list of Pete Davidson’s girlfriends. What was even more intriguing? The two had a substantial age gap of 20 years, proving that love knows no bounds, especially when it comes to the SNL comedian.

Rumours about their budding romance became rife when they were caught flirting at a Golden Globes after-party in January 2019. Their PDA left no room for speculation. In March of that year, during a New York Rangers game, the two were seen locking lips, officially confirming their relationship status. However, their passionate fling wasn’t meant to be and they decided to part ways in April 2019. As per insiders, the intensity of the spotlight on their relationship was too much to bear.

Margaret Qualley: (August 2019 – October 2019)

Just a few months after parting ways with Kate Beckinsale, Pete briefly crossed paths with actress Margaret Qualley, known for her role in Once Upon a Time in Hollywood. While the rumour mill started buzzing about their relationship in August 2019, by October of the same year, it was all over. Their romance may have been short-lived, but it added another intriguing name to Pete Davidson’s long list of girlfriends.

Kaia Gerber: (December 2019 – January 2020)

Pete Davidson was far from done in 2019. He swiftly moved on to Kaia Gerber, the daughter of supermodel Cindy Crawford and businessman Rande Gerber. Their relationship kicked off in October, and they were frequently seen together, even enjoying a romantic getaway in Miami.

Despite their public outings, rumours swirled that Kaia’s parents hoped the relationship would fizzle out. And, indeed, it did. By January 2020, Pete and Kaia had called it quits. During this time, Pete was navigating personal challenges and sought help by checking into rehab, something he openly discussed. In an interview with Page 6, he stated that “It just wasn’t the right place or the right time at all” while reflecting on their parting.

Olivia O’Brien (2020)

Pete Davidson girlfriends
Picture Credits: Courtesy Instagram/Olivia O’Brien

The long list of Pete Davidson’s girlfriends continued in 2020 as rumours circulated about his fling with singer Olivia O’Brien. Although Davidson denied their relationship, O’Brien claimed they had a secret but brief relationship that began in October 2020. She revealed that Pete broke things off via text, a revelation she made on the BFFs podcast in June 2022. Despite the ending, O’Brien had only kind words for Davidson, praising him as a “nice guy.” 

Like most other ladies, Olivia couldn’t help but gush about his good looks, humour and sweetness that drew her to him.

Phoebe Dynevor: (2021)

In another surprising twist in his love life, Pete Davidson ventured into a romance with Bridgerton star Phoebe Dynevor. Their love story blossomed in April 2021, but by August of the same year, they had decided to part ways. The geographical distance between them, with Dynevor residing in the UK and Davidson in New York City, is believed to have been a significant factor in their separation. Despite the brief duration of their relationship, the couple did make headlines with their first public appearance together at the 2021 Wimbledon Open.

Kim Kardashian: (November 2021 – August 2022)

Davidson’s wild love life made headlines once again in October 2021 when he and Kim Kardashian raised eyebrows after being spotted hand in hand during a roller coaster ride, a public display of affection that followed their on-screen kiss in an SNL skit.

At the time, speculation about the two dating was rife, though insiders insisted they were merely “just friends.” Shortly thereafter, reports of Davidson orchestrating an intimate dinner for the two on Staten Island started doing the rounds. Their connection deepened as they were observed sharing affectionate moments during a second date night in the streets of NYC. November brought official confirmation from various news sources, solidifying their status as a couple.

In June 2022, during an episode of the show The Kardashians, Kim noted that the comedian had a special presence in her life and said, “Pete is such a good person. I can’t even explain it. He just has the best heart and always thinks of the small things.”

Unexpectedly, their high-profile romance came to an end in August 2022 after nine months of dating. Sources revealed that the pair’s hectic work schedules simply weren’t allowing them to maintain a romantic relationship.

Emily Ratajkowski: (November 2022)

 

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Fresh from his breakup with Kim Kardashian, Pete’s dating escapades didn’t pause. He was reportedly dating model and entrepreneur Emily Ratajkowski in November 2022. Their connection, fostered through mutual friends, was in its early stages. Ratajkowski had previously spoken about Pete’s charm, highlighting his vulnerability, warmth, style and height as factors that make him appealing to women.

Chase Sui Wonders (December 2022 – August 2023)

Following the rapid end of his connection with Ratajkowski, Pete Davidson’s dating history took another twist as he started spending more time with his Bodies, Bodies, Bodies co-star Chase Sui Wonders.

They were first spotted enjoying a dinner outing and hanging out at the comedian’s apartment in NYC in December 2022. However, their romance wasn’t officially confirmed until the subsequent month when they were seen publicly holding hands and sharing kisses during a visit to Universal Studios Hollywood.

In August 2023, a source confirmed to the media that the two had decided to part ways, concluding a relationship that had lasted for less than a year. This announcement came approximately two months after reports that Pete Davidson had voluntarily checked himself into rehab, seeking assistance to cope with borderline personality disorder (BPD) and PTSD.

Madelyn Cline (September 2023 – Present)

Pete Davidson’s most recent romance, as of 2023, is with actress Madelyn Cline, best known for her role in Outer Banks. Their love story began in September and became evident during one of Pete’s stand-up comedy performances in Las Vegas that Cline attended to offer her support.

Their connection continued to blossom in October when Pete returned to host the premiere of SNL. The couple made a striking entrance at the show’s afterparty, hand in hand, signalling that their love story was still very much alive. 

(Header and feature image courtesy: Credits: Instagram/Saturday Night Live, Kim Kardashian and Ariana Grande)

This story first appeared on Augustman.

Frequently Asked Questions (FAQs)

– Who is Pete Davidson dating recently?
Pete Davidson is currently dating actress Madelyn Cline.

– Who did Pete Davidson date for the longest time?
Pete Davidson’s longest publicly known relationship was with Cazzie David. He dated her dating from 2016 to 2018.

– How long did Pete Davidson and Kim Kardashian date?
Pete Davidson and Kim Kardashian dated for approximately nine months, from November 2021 to August 2022.

Ariana Grande celebrities culture Kim Kardashian Pete Davidson pop culture relationships
All of Pete Davidson’s Girlfriends in Chronological Order

Kratagya Rathore

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