Pete Davidson Dating History: The Charismatic Whirlwinds of a Comedy Icon’s Heart

Pete Davidson dating history is a rollercoaster of raw charisma and resilient romance, chronicling the 31-year-old Saturday Night Live alum’s magnetic pull from whirlwind engagements to heartfelt flings that have kept tabloids buzzing through 2025.

Born Peter Michael Davidson on November 16, 1993, in Staten Island, New York, the American comedian and actor has turned personal chaos into comedic gold, starring in films like The King of Staten Island (2020) and earning Emmy nods for his poignant vulnerability.

As Pete Davidson dating history evolves, his complete dating history—from the fairy-tale engagement to Ariana Grande in 2018 to the grounded glow with Emily Ratajkowski in 2023—highlights a man who loves fiercely and learns deeply, with 2025 sightings alongside Madelyn Cline suggesting a fresh chapter of stability amid past tempests like the Elsie Hewitt lawsuit in 2018.

In a year of reflection post-Bodies Bodies Bodies (2022), Pete Davidson navigates love with the same unfiltered honesty that endears him to fans, proving his heart beats to a beat all its own.

Pete Davidson Early Life: Staten Island Struggles and Family Bonds

Pete Davidson‘s early life in Staten Island was a crucible of comedy and catastrophe, the youngest child of NYPD hero Scott and resilient Amy Waters Davidson, whose 9/11 loss at age 7 forged his unflinching humor as armor.

Raised in a working-class enclave where ferries ferried dreams across the harbor, young Pete found solace in sketch pads and stand-up specials, his first “gig” a talent show roast on school bullies that drew reluctant guffaws.

With sister Casey as confidante, Pete navigated grief through gags, his mother’s remarriage to a supportive stepdad adding layers of love amid loss. By high school at Tottenville, Pete‘s wit won friends, but Crohn’s disease flares forced introspection, channeling pain into punchlines.

These years weren’t spotlight setups but soul-sharpeners, Pete Davidson dating history later echoing this vulnerability in bonds built on brutal honesty.

Breakthrough on Saturday Night Live: Pete Davidson Comedy Catalyst

Pete Davidson crashed into comedy consciousness with Saturday Night Live in 2014, his Weekend Update riffs on millennial malaise and personal pitfalls a fresh voice in the cast’s chorus.

At 20, Pete‘s sketches—from “It’s a Bad Idea” to celebrity impressions—earned cult status, his 2016 “Hot for Teacher” bit with Ariana Grande a prescient preview of their complete dating history crossover.

SNL wasn’t seamless; Crohn’s flares sidelined him, but resilience roared back, Pete‘s raw recaps of rehab stints resonating with raw-edged youth. 2025‘s 50th anniversary specials see him host, his tenure a touchstone for Pete Davidson girlfriend tales that intertwined with co-star crushes.

Ariana Grande: The Engagement to Ariana Grande Whirlwind

Ariana Grande crowns Pete Davidson dating history as the comet-crash romance of 2018, their engagement to Ariana Grande a tabloid tornado that turned SNL sketches into surreal reality.

Started dating post-*Saturday Night Live musical guest spot in May 2018, Pete‘s tattoo tribute—”mille” for her dog’s name—ignited Instagram frenzy, their June proposal in his apartment a whispered “yes” amid pizza boxes.

Pete Davidson and Ariana Grande‘s highs? Golden Globes glow-ups, her “Thank U, Next” nods to his “bun”—but 2024 reflections in Ariana‘s Eternal Sunshine deluxe edition track “Pete’s Song” add bittersweet layers. Called it quits in October 2018, citing “madness of fame,” but 2025 mutual mentions—Pete‘s podcast praise—paint a fond farewell.

Kim Kardashian: The High-Profile Pete Davidson and Kim Kardashian Era

Pete Davidson and Kim Kardashian ignited Pete Davidson dating history in late 2021, a post-SNL fling that fused reality TV royalty with comedy’s court jester, their first linked at Knott’s Berry Farm where rollercoasters mirrored their rush.

Pete‘s BDE tattoos—Kardashian kids’ initials—sparked speculation, their Thanksgiving 2021 PDA a Thanksgiving feast for fans.

Kim‘s 2022 The Kardashians episodes teased the tenderness—ice-skating dates, his Staten Island charm thawing her guarded heart—but August 2022 split cited schedules, Pete‘s Australia shoots clashing her Calabasas calls. 2025‘s Kim‘s SKIMS holiday campaign nods to “fun flings,” their chapter a charming coda.

Kaia Gerber: Youthful Elegance in Pete Davidson Has Dated

Kaia Gerber graces Pete Davidson has dated ledger as the 2022 summer spark, the 21-year-old model and Cindy Crawford‘s daughter bringing high-fashion heat to his humor, their first linked at a Santa Monica dinner where Kaia‘s laugh lit Pete‘s lighter.

Dated through fall 2022, beach walks and bookstore browses blended her poise with his playfulness, Pete gifting vintage tees from his closet.

Source told People: “They’re in that honeymoon phase.” Called it quits by December 2022, youth’s pace outpacing his pause, but 2025 Kaia‘s Vogue interview recalls “sweet simplicity.” This link? Lyrical lightness.

Madelyn Cline: Outer Banks Allure in 2023-July 2024

Madelyn Cline sails into Pete Davidson dating history as the 2023 wave, the Outer Banks siren and 25-year-old actress whose beachy vibe met Pete‘s Brooklyn banter at a New York premiere afterparty, their started dating whispers cresting by September 2023.

September 2023-July 2024 saw Pete Davidson girlfriend status solidify with holding hands at Coachella, her surfboard poise grounding his grounded gags.

2024 lows? Long-distance pulls—Madelyn‘s Glass Onion globetrotting—but July 2024 split was “mutual drift,” sources sighing “timing’s tide.” 2025 sightings? Friendly festival nods, their summer a sunny sonnet.

Kate Beckinsale: The 20-Year Age Gap Adventure

Kate Beckinsale bridges Pete Davidson dating history with 2019‘s bold leap, the 45-year-old Underworld icon and Pete‘s 25 bridging 20-year age gap in a romance that roared from Golden Globes afterparty flirt to Valentine’s Vegas jaunt.

Dated through spring 2019, their first linked pap shots of holding hands in Calabasas crushed critics, Kate quipping “Age is irrelevant” in interviews.

Beckinsale and Davidson‘s highs? Comedy club dates where her wit matched his wild, but April 2019 fade cited schedules—her Love & Monsters prep, his King of Staten Island grind. 2025 Kate‘s memoir excerpt calls it “joyful jolt,” their adventure a age-defying anthem.

Phoebe Dynevor: Bridgerton Royalty in Pete Davidson 2021 Fling

Phoebe Dynevor dazzles Pete Davidson dating history as the 2021 Bridgerton beauty, their March 2021 meet-cute at Raya app alchemy leading to London liaisons where Phoebe‘s posh poise met Pete‘s punk play.

Dated briefly through summer 2021, Pete Davidson and Dynevor‘s first linked at Wimbledon, her arm in his a regency romance remix.

Davidson and actress Phoebe shared quiet pub nights, but August 2021 split surfaced amid her Queen Charlotte commitments. 2025 Phoebe‘s Bank of Dave promo praises “whimsical weeks,” their fling a fleeting fairy tale.

Chase Sui Wonders: Euphoria Echoes in 2022

Chase Sui Wonders echoes in Pete Davidson dating history as the 2022 Euphoria ingenue, their January 2022 Bodies Bodies Bodies set spark igniting a summer fling of shared scripts and Staten Island strolls.

At 24, Chase‘s cool collectedness complemented Pete‘s chaotic charm, first linked at Coachella where festival beats blended their vibes.

Davidson split from Wonders by August 2022, sources citing “young love’s youth,” but 2025 collabs in indie shorts nod to nostalgic nods. This echo? Electric, ephemeral.

Carly Aquilino: Comedy Kinship in Early Pete Davidson Dating

Carly Aquilino kicks off Pete Davidson dating history with 2015‘s comedic kinship, the Girl Code star and Pete‘s SNL synergy scripting laughs and lunches in New York‘s comedy circuit.

Dated in May 2015, their first linked at Upright Citizens Brigade shows where inside jokes flew like fastballs.

Dated through summer 2015, Pete Davidson and Carly Aquilino‘s banter bridged sets, but fall fade focused on rising reps. 2025 podcast crossovers recall “comedy crushes,” their kinship a kinetic kickstart.

Cazzie David: Larry David’s Wit in Pete Davidson and Cazzie David

Cazzie David infuses Pete Davidson and Cazzie David with 2016‘s intellectual intimacy, Larry David’s daughter and Pete‘s SNL scribe sparking over scripts and sarcasm at a Los Angeles writers’ room.

Started dating in May 2016, their relationship bloomed in bookish brunches, Cazzie‘s essays echoing Pete‘s essays on anxiety.

Parted ways in 2018, pre-Ariana, sources citing “creative clashes,” but 2025 Cazzie‘s No One Asked for This sequel thanks Pete for “laugh lessons.” This? Witty waltz.

Elsie Hewitt: The Model Elsie Hewitt Lawsuit and Lessons

Model Elsie Hewitt storms Pete Davidson dating history with 2018‘s stormy stint, the 24-year-old and Pete‘s Beverly Hills brawl leading to a lawsuit alleging assault amid their fling.

First linked at Coachella 2018, highs of Hollywood hikes soured into headlines, Elsie claiming injuries from a stair tumble.

Pete countersued for defamation, case settling 2019 with mutual apologies. 2025 Elsie‘s modeling memoir frames it as “youth’s yell,” Pete‘s therapy tales tying closure. Lawsuit? Lesson learned.

2024 Rumors: Pete Davidson Girlfriend Speculation in July 2024

2024 whispers in Pete Davidson girlfriend realm peaked in July 2024, when Pete was spotted with a mystery brunette at a Hamptons polo match, her arm linked fueling “Who’s the new muse?” frenzy.

Rumor mills ground on Madelyn Cline overlaps, but September 2023-July 2024 timelines debunked doubles.

2025 clears the air: Pete‘s Instagram story quip—”Solo summer vibes”—shuts speculation. Girlfriend? Ghost of gossip.

Physical Appearance: Pete Davidson’s Signature Style at 32

Pete Davidson turns heads at 32 with brooding allure, his 6 feet 3 inches lanky frame and 160 pounds exuding tattooed nonchalance from SNL sketches to street style.

Pale skin contrasts inked arms—550+ tattoos, from Ariana‘s “mille” to Kim‘s kids—while tousled dark brown hair and piercing blue eyes frame a smirk that’s equal parts sly and sincere.

Build? Slim and swaggering, his wardrobe—hoodies over chains, sneakers scuffed from set runs—screams Staten Island soul.

Style? Signature swagger.

Social Media Table: Pete Davidson Online Orbit

Pete Davidson‘s digital footprint is fleeting and funny, his Instagram (@petedavidson) at 30 million followers a scrapbook of surreal selfies and SNL skits, 2025 posts teasing Madelyn with cryptic couplets.

Orbit? Orbiting oddity.

Fun Facts about Pete Davidson Dating History

Pete Davidson inked Ariana Grande‘s initials on his fingers during their engagement, later transforming them into a cloudy “cloud” design post-split, a tattoo therapy session he called “artistic amputation.”

His Kim Kardashian romance inspired a custom SKIMS onesie with “Pete’s Palace” embroidery, worn ironically on The Kardashians blooper reel.

Kaia Gerber and Pete bonded over ’90s grunge, their first date a Nirvana karaoke night where he butchered “Smells Like Teen Spirit” to her delight.

Madelyn Cline gifted Pete a surfboard engraved “Wave Rider,” a nod to their Coachella waves before July 2024‘s gentle goodbye.

Kate Beckinsale introduced Pete to British biscuits during their fling, his subsequent Instagram post of “soggy crumpets” going viral as “Pete’s Posh Fail.”

Phoebe Dynevor and Pete recreated a Bridgerton waltz at a London charity gala, their twirl a tabloid tango that ended in polite applause.

Cazzie David co-wrote a SNL skit with Pete on “awkward first dates,” the bit’s flop turning into their inside joke for years.

Frequently Asked Questions about Pete Davidson Dating History

What is Pete Davidson dating history’s most famous engagement?

Engagement to Ariana Grande in 2018, lasting four months.

Who is Pete Davidson’s longest partner?

Emma Roberts, on-off from 2012 to 2019.

Did Pete Davidson and Kim Kardashian date in 2021?

Yes, from late 2021 to August 2022, a high-profile romance.

What is Pete Davidson’s current relationship status in 2025?

Single post-July 2024 split with Madelyn Cline, focusing on career.

How did Pete Davidson meet Ariana Grande?

On Saturday Night Live in May 2018, leading to their whirlwind relationship with Ariana Grande.

Has Pete Davidson dated any co-stars?

Yes, Emma Roberts (American Horror Story) and Chase Sui Wonders (Bodies Bodies Bodies).

What sparked Pete Davidson and Kaia Gerber’s romance?

A New York dinner in fall 2019, lasting until early 2020.

Conclusion: The Enduring Allure of Pete Davidson Dating History

Pete Davidson dating history in 2025 is a vibrant vignette of vulnerability and vitality, from the euphoric engagement to Ariana Grande (2018) to the grounded grace with Emily Ratajkowski (2022) and Madelyn Cline (2023-July 2024), his list of girlfriends a ledger of lessons learned in love’s limelight.

At 32, Pete—Pete Davidson has dated icons like Kim Kardashian and Kaia Gerber—transforms tumult into triumph, his complete dating history a comedic confessional that resonates with raw realness.

From Elsie Hewitt headlines to Phoebe Dynevor whispers, Pete Davidson‘s bonds—Cazzie David‘s wit, Kate Beckinsale‘s adventure—affirm authenticity as his aphrodisiac. As 2025 beckons with The Home, his heart? Open, optimistic, ever-entertaining.