Pete Davidson’s love life reads like a horoscope written on Red Bull. Chaotic, unfiltered, and impossible to ignore, it has more plot twists than a Marvel multiverse. Every girlfriend is a headline, every breakup a cultural event, and every public display of affection a minor scandal waiting to trend. It is messy, it is flashy, and it is exactly the kind of wild ride that makes the tabloids cash checks while his fans just watch in awe. 

While the world whispers about comedy gigs and awards, Pete Davidson’s love life screams like a siren in Times Square, full of sparks, drama, and high-profile romances that read like a chaotic, unskippable playlist.

In 2015, Pete Davidson and comedian Carly Aquilino shared laughs in New York comedy clubs while the world barely noticed. While his presence radiated chaotic energy, their romance stayed soft-focus, fleeting yet sweet. They parted ways by the end of the year, but friendship lingered like the aftertaste of a perfect espresso. Aquilino even popped up in The King of Staten Island, proving that sometimes breakups come with cameo appearances and subtle shade.

While soft laughter faded in small comedy clubs, the stage was already primed for a messier, more headline-hungry romance that would rewrite Pete Davidson’s reputation for complicated love.

Pete Davidson and Cazzie David were the embodiment of complicated love: witty, messy, and impossible to ignore. They dated for about two years, ending in May 2018, shortly before Davidson’s whirlwind romance with Ariana Grande. David later chronicled their highs and heartbreaks in No One Asked For This, revealing the shock of watching her ex move on so publicly and quickly. While their romance ended, they reconciled into friendship, proving that even messy love stories can leave room for respect and maturity.

While two years of complicated love simmered into friendship, Pete Davidson was already lighting sparks elsewhere, preparing a romance so loud and public it could not possibly go unnoticed.

Pete Davidson and Ariana Grande’s romance detonated like a firework on New Year’s Eve. Instagram went nuclear, engagement rings flashed, and within five months, the fairy tale collapsed. 'Thank u, next' immortalized his "Big Di-- Energy," sealing him in pop culture lore. Love was fast, loud, and unavoidably memeable. It was proof that when Davidson dates, the world watches, X posts, and remixes, turning private passion into a public spectacle that is as entertaining as it is slightly tragic.

While fireworks faded and memes circulated, Davidson’s chaotic love life pivoted to a new headline, this time with Hollywood glamour, age gaps, and paparazzi ready to throw confetti or shade.

Flirting at Golden Globes and smoldering at Rangers games, Pete Davidson and Kate Beckinsale were a spectacle of curiosity and disbelief. While his energy buzzed, the twenty-year gap and relentless media glare made romance feel like a circus act. Four months later, the sparks fizzled, not for lack of chemistry, but because fame is a relentless chaperone. Hollywood loves a scandal, but even it cannot manufacture love that can survive a paparazzi hurricane.

While sparks flew and cameras clicked, the next flame was already lighting up the horizon, ready to break feeds again.

Pete Davidson and Margaret Qualley shared a brief, whirlwind romance in late summer and early fall of 2019. They glided like whispers through Venice, attending festivals without demanding headlines. Their connection shimmered quietly, intimate yet almost scandalous in a world used to Davidson’s chaotic, screaming romances. By October, the chapter closed gracefully, turning love into friendship without fanfare. Qualley, the cupid herself, has since married musician Jack Antonoff, proving some sparks flicker fast but leave a warmth that lingers.

While Venice whispered and sparks faded gracefully, Pete Davidson’s orbit shifted to glamour and responsibility, proving that even in chaos, love sometimes bows to boundaries and a little self-preservation.

At that time, Pete Davidson, 26, and Kaia Gerber, 18, shared a brief romance that blended glamour with self-awareness. While his eyes oozed charm and his presence lit the room, he paused the relationship to prioritize mental health. Gerber, young and free, deserved fun, not therapy sessions in designer shops. Parents nodded approvingly, red carpets shimmered, and the breakup felt responsible rather than dramatic. Rarely does a celebrity romance end without fireworks, proving even chaos sometimes respects boundaries.

While responsible boundaries ruled with Kaia Gerber, Pete Davidson’s romantic compass shifted overseas, diving into long-distance chaos where love became public performance, headlines, and social scrutiny rolled into a transatlantic spectacle.

Pete Davidson and Phoebe Dynevor navigated five months of love across oceans, with social scrutiny always on speed dial. While his energy remained chaotic and magnetic, her reflection on naivety revealed that celebrity romance is a full-contact sport. Distance and constant attention turned even simple dates into headlines, proving that when Davidson dates, it is never just private; it is a performance, a press conference, and a trend rolled into one.

While transatlantic drama tested patience and paparazzi endurance, Pete Davidson’s orbit collided with Hollywood royalty, turning Saturday Night Live sketches and red carpets into headline-fueled chaos only he could make somehow intimate.

From a Saturday Night Live sketch kiss to matching outfits on red carpets, Pete Davidson and Kim Kardashian were headline fuel. Conflicts with Kanye West, now Ye, and long-distance logistics ended the nine-month saga, but not before every photo, meme, and wardrobe choice became cultural property. Love in this context is performative and intimate at the same time, a chaotic paradox only Davidson could navigate without missing a beat.

While red carpets blazed and memes immortalized chaos with Kim Kardashian, Pete Davidson’s orbit shifted to a shorter, flashier spark with Emily Ratajkowski, proving that even amidst headlines and paparazzi, some celebrity romances can zip past with style and barely a ripple of drama.

Pete Davidson’s month-long fling with Emily Ratajkowski was stylish, public, and brief. Knicks games and cozy appearances marked November, but by December, the romance had cooled into friendship. Celebrity flings can be lightning-fast, proof that even Davidson’s chaos can sometimes burn bright and vanish just as quickly, leaving only a fleeting aesthetic memory and a handful of paparazzi photos.

While November fizzled, Hollywood chemistry brewed elsewhere, prepped for public vacations and viral headlines.

Pete Davidson and Chase Sui Wonders navigated a nine-month romance that was part personal, part professional. Vacations, puppy adoption, and public dates made the love both adorable and chaotic. In true Hollywood fashion, the relationship ended amicably, transforming into a friendship almost immediately. Sometimes, love with Davidson is less a fireworks show and more a perfectly timed montage, little bursts of chaos, charm, and sweetness edited together like the highlight reel Hollywood wishes it could direct.

While projects wrapped, the dating set remained live, anticipating Madelyn Cline’s quieter but headline-ready entrance.

Nearly a year of romance with Outer Banks star Madelyn Cline passed with less virality but equal style. Public events spotted, subtle public display of affection noted, and eventual separation in July 2024 reminded fans that even amidst chaos, some love stories can simmer quietly, though never for long in Pete Davidson’s orbit.

While low-key moments passed, Elsie Hewitt’s chapter awaited, promising babies, headlines, and inevitable chaos.

Pete Davidson and Elsie Hewitt began dating in March 2025, announcing their pregnancy by July. Davidson, ecstatic at impending fatherhood, finally embraced something profoundly grounding. Love, family, and thoughts of marriage now intertwine with chaos, proving that sometimes the wildest dating history culminates in the most human, chaotic, and surprisingly sweet reality check.

Pete Davidson Reveals Why Having a Child Means Everything After His Darkest Days

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