Pete Davidson’s Honestly Amazing Dating History

Pete Davidson is just 25 years old, but you wouldn’t know it by counting the rings!

Yes, the Saturday Night Live star’s dating life is that of a much older man, full of starlets, pop stars, and A-list actresses. And lots of daughters of very famous people…

He basically really is his Chad character in real life.

We don’t know if it’s his tattoos, his body, his self-deprecating sense of humor, but the man has pulled some of the hottest, most talented, eligible ladies around.

So who all has Pete dated in his half decade in the spotlight?

See our full timeline of the unlikely Lothario’s love life (below)!

Carly Aquilino

Carly Aquilino dated Pete Davidson
Carly Aquilino at the 2016 MTV Video Music Awards. / (c) Ivan Nikolov/WENN

Pete and the Girl Code comedian dated in 2015, though not much is known about their relationship or their breakup.

They do seem to be on good terms as they’ve been photographed together as recently of February 2019.

Cazzie David

Cazzie David dated Pete Davidson
Cazzie David and Pete Davidson at the Comedy Central Roast Of Rob Lowe. / (c) FayesVision/WENN

So far as we know, the longest romantic relationship of Pete’s life was with the comedy writer. The two were together from 2016 to May 2018 and until the sudden split were nonstop being cutesy and gushing over one another in interviews and on social media.

He even got a tattoo of her face. For real.

Pete Davidson Cazzie David tattoo
Turns out that likeness was better than their chances. / (c) Instagram

Cazzie is also the daughter of Seinfeld and Curb Your Enthusiasm creator Larry David. It’s the beginning of an inneresting predilection Pete seems to have for romantic partners.

Cazzie David daughter of Larry David
Cazzie with poppa Larry David at the Season Nine premiere of ‘Curb Your Enthusiam’. / (c) Patricia Schlein/WENN

According to sources, Pete asked Cazzie to marry him, but it wasn’t meant to be…

Ariana Grande

Ariana Grande and Pete Davidson
Ariana Grande and Pete Davidson at the 2018 MTV Video Music Awards. / (c) WENN

In the Summer of 2018, Ariana Grande shocked the world by suddenly getting engaged to the rising SNL star.

The two became the encyclopedia picture for “whirlwind romance” as they started dating in May, were engaged in June, and were dunzo by October. At first the split seemed somewhat amicable, though still obviously devastating emotionally. But breaker upper Ari made it much worse a few months later when she called him “a distraction” from her breakup with Mac Miller, telling Vogue:

“I met Pete, and it was an amazing distraction. It was frivolous and fun and insane and highly unrealistic, and I loved him, and I didn’t know him.”

Ouch.

Pete may have been embarrassed by a lot of the sudden attention on his love life — and indeed his sex life, as he was the poster boy for new term “big dick energy” — but the relationship left a lasting mark on his reputation as a star and as a stud.

Kate Beckinsale

Kate Beckinsale dated Pete Davidson
(c) Patricia Schlein/WENN

In January of 2019, Pete was spotted getting flirty with the Underworld star at the Golden Globes.

Suddenly they were a full-blown item, proudly putting their chemistry on display in public, including now infamously at a hockey game, becoming — along with the poor Queer Eye cohost sitting alone beside them — a meme.

The relationship lasted a solid couple months but by April we learned they were no longer “on romantic terms” with one another.

Margaret Qualley

Margaret Qualley dated Pete Davidson
(c) KIKA/WENN

Margaret Qualley is a future movie star just waiting for that breakout lead role, a real actress on the rise. So obviously it was her turn to date Pete Davidson this year.

We first learned Pete and the Once Upon A Time In Hollywood actress were together in August as he was her plus one at the Venice Film Festival premiere of her new movie Seberg.

The two kept things much more private than Pete’s previous relationships; heck, we apparently didn’t even know about it until two months in! And he elected not to even join her on the Venice red carpet.

Probably a good choice in the long run as they had split less than two months later, a duration right about at the median for Pete: four months.

BTW, speaking of trends, Margaret is the daughter of Four Weddings and a Funeral star Andie MacDowell. Huh.

Kaia Gerber

Kaia Gerber dated Pete Davidson
(c) Laura Villani/KIKA/WENN

The most recent young woman (emphasis on young this time) to date Pete is model Kaia Gerber.

Besides finding a lot of success in her own right in the fashion industry so far, the 18-year-old is also notably the daughter of supermodel di tutti capi Cindy Crawford.

Kaia Gerber with momma Cindy Crawford
Kaia Gerber with her famous momma. / (c) Cindy Crawford/Instagram

Neither has confirmed the coupling, but in late October 2019 Pete was spotted leaving the teen’s apartment, and the two were photographed on a brunch date in New York City.

If you’re thinking it feels like Pete is too old for Kaia, don’t worry — it’s not just the whole “old dating energy” thing. Strictly speaking she does fall below the arbitrary but somehow consistently reasonable half-age-plus-seven-years rule for the 25-year-old comic. But it’s not like we’re in James Woods territory or anything.

Time will tell if this one is the keeper. But our money is on four months…

[Image via Apega/Adriana M. Barraza/NBC/WENN/Ariana Grande/KENZO/YouTube.]

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