Pete Davidson’s Dating Timeline: From Ariana Grande and Kim Kardashian to Kaia Gerber and Beyond

Pete Davidson’s Star-Studded Love Life: A Timeline

When it comes to the dating world, few have had a love life as star-studded and eventful as comedian Pete Davidson. With a relationship history dotted with A-list celebrities and whirlwind romances, Pete’s love life has been a constant topic of discussion in Hollywood.

Pete and Cazzie David: An Unsettled Beginning

Pete’s romantic journey with celebrities began in 2016 when he started dating Cazzie David, the talented daughter of renowned comedian Larry David. They were together for two and a half years. However, their relationship had its share of rocky moments. In her enlightening book of essays, “No One Asked for This,” Cazzie shed light on their tumultuous relationship, revealing that just two days after their breakup in 2018, Pete began dating pop sensation Ariana Grande. A concerning element of their time together was Cazzie’s struggle to assure Pete of her love, especially given his history with “self-harm and suicide threats.”

The Ariana Grande Whirlwind

The world watched in awe as Pete’s relationship with Ariana Grande took off at supersonic speed. Merely weeks into dating, the lovebirds decided to share a nest and even announced their engagement in June 2018. However, by October, the fairy-tale seemed to have lost its magic as the couple announced their split. The emotional aftermath was evident when, in December, Pete alarmed fans with a distressing tweet. Ariana’s attempt to reach out was reportedly rebuffed.

Short-lived Romances: Beckinsale to Gerber

2019 was a year of quick flings for Pete. Starting off the year, Pete and actress Kate Beckinsale ignited dating rumors after they were spotted together at a post-Golden Globes bash. Their relationship, however, was fleeting. As summer approached, Pete found solace in the company of actress Margaret Qualley. Yet, as quickly as this romance began, news soon broke of its end. Without missing a beat, Pete was soon in the spotlight with model Kaia Gerber. Their Miami getaway in November 2019 was a paparazzi favorite. However, whispers in Hollywood suggested that Kaia’s parents, the legendary Cindy Crawford and Rande Gerber, harbored concerns over Pete’s mental well-being. As 2020 dawned, the pair decided to part ways.

A Bridgerton Affair and a Kardashian Chapter

The heart wants what it wants, and in 2021, it led Pete to the “Bridgerton” star, Phoebe Dynevor. Their Wimbledon date in July was the talk of the town. But the pressures of work and distance saw their story end in August. Yet, Pete’s next romantic chapter was waiting just around the corner. After sharing a playful kiss on Saturday Night Live with Kim Kardashian in October, the two embarked on a nine-month-long relationship, only to part ways in August 2022 due to work commitments.

Recent Rendezvous: Emily to Chase

The final quarter of 2022 saw Pete romantically linked with model Emily Ratajkowski. Their relationship, however, was as brief as it was intense, culminating at a Knicks game in late November. December introduced a new name to Pete’s list – his “Bodies Bodies Bodies” co-star, Chase Sui Wonders.

Their decision to stay away from the limelight, evident from their separate entrances during the premiere of “Bupkis,” added an element of mystery. Chase’s recent comments in May 2023 about their “sacred” relationship hinted at a deeper bond. Unfortunately, by August 2023, the curtain fell on this chapter as well.

Pete Davidson’s love life has been a roller-coaster of emotions, filled with highs and lows. But with each relationship, we get a glimpse into the heart of a man seeking love, understanding, and connection in the bright and often unforgiving spotlight of Hollywood.