Pete Davidson Isn't The Ultimate Rebound Boyfriend — He's Preying On His Exes' Vulnerability

Pete Davidson's dating history is somewhat problematic.

Emily Ratajkowski, Pete Davidson, Ariana Grande, Kim Kardashian YouTube / Ovidiu Hrubaru / Debby Wong / lev radin / Shutterstock

Pete Davidson is no stranger to the drama of high-profile celebrity relationships. In fact, he's basically the king of it by now.

Davidson's dating habits have long bewildered the internet and earned him the title of "The Ultimate Rebound."

His dating history is full of tumultuous highs and lows — and his newest relationship seems to be no different. 

Since breaking up with Kim Kardashian in August 2022, the 29-year-old comedian is rumored to be dating model and author Emily Ratajkowski. 


Ratajkowski, who recently separated from her husband, Sebastian Bear-McClard, was spotted getting close to the "King Of Staten Island" star in his latest of many public romances.

RELATED: Pete Davidson Dumped Kim Kardashian After Seeing A ‘Contrived’ Clip From Her Hulu Show, Claims Source

But the infamous serial monogamist is starting to raise eyebrows from fans questioning the motive behind his high-profile escapades.


Pete Davidson may be scoring dates with some of the world's most famous women — but is he preying on their vulnerability?

That is the question being raised by fans in a Reddit group dedicated to the Kardashians and, though it is one derived from a group who may be biased towards one of Davidson's exes in particular, it is an interesting one nonetheless.

"Why is Pete so glorified for landing beautiful women when in reality he targets vulnerability," asks a fan, pointing out that Davidson's exes are often "Women who just got out of horrible/abusive relationships."

Let's start by acknowledging that each of Davidson's exes are consenting adults with their own agency and their prior relationships in no way define them. However, as this fan on Reddit noted, Davidson met many of his exes at a vulnerable time in their lives.

Ratajkowski and Davidson's rumored romance follows her high-profile split with Bear-McClard who allegedly cheated on her repeatedly shortly after she gave birth to their son.


Davidson was Kardashian's first public relationship after her 2021 split from husband Kanye West.

RELATED: Fans Spot 'Proof' Kim Kardashian Flew To See Pete Davidson After His 'Major Meltdown' While Filming TV Show

Davidson dated Kardashian at possibly one of the most unstable points in her life.

West has shown multiple signs of emotional abuse toward Kardashian in his many public outbursts during and since their marriage.

During the comedian and reality star's nine-month fling, West regularly made threats against his ex-wife's new partner, slammed her online, and used their children as leverage to bully her into speaking to him.

Diving back even farther into Davidson’s past, it’s not a stretch to say that he makes impulsive romantic decisions. In 2018, Davidson broke off his two-and-a-half-year relationship with Cazzie David via text, then announced his new relationship with Ariana Grande on Instagram the following day. 


Cazzie David described the negative effect dating Davidson had on her mental health.

David, in her 2020 personal essay collection "No One Asked For This," detailed a frequent state of feeling "emotionally exhausted" while dating Davidson due to his own mental health issues.

"Self-harm and suicide threats had come about from trivial circumstances, incidents that would go from 0 to 100, which were so momentarily urgent, like the last minute of an escape room before the time goes off, except I'm the only one in the room and all the clues are tricks," she recalled.

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Davidson and Grande's media-dominating relationship also took a toll on David.


"My panic and shame were so far past overdrive, I couldn't articulate what it was I was even feeling," she wrote. And while David is ultimately complimentary towards her ex there is no denying that she was mistreated at the end of their relationship.

Davidson and Grande's relationship itself is a whole different beast.

Grande was dealing with numerous personal traumas before dating Davidson.

The two started dating after Grande's split from Mac Miller, a relationship that was marred by the rapper's drug abuse, causing Grande to frequently get blamed by fans for his health issues and his untimely death in 2018. 

Davidson and Grande's relationship, which rapidly turned into an engagement after weeks of dating, also began just a year after the 2017 terrorist attack at Grande's Manchester concert and ended shortly after Miller's death.


To say Grande was in a fragile state before and during their romance would be an understatement.

Grande has been quoted as saying that their time together was “frivolous and fun and insane and highly unrealistic, and I loved him, and I didn’t know him.”

Davidson went on to date Kaia Gerber from October 2019 to January 2020. At the time of their relationship, Davidson was 26 and Gerber was only 18.

RELATED: Rumor That Pete Davidson Sent Intimate Photos Of Ariana Grande To Mac Miller Resurfaces After His Texts To Kanye West

Gerber allegedly found it overwhelming to date Davidson. 

The age gap creates an obvious imbalance but an insider's description of their relationship may also speak to his treatment of his partners.


After their relationship ended when Davidson checked into a rehabilitation facility, a source told Page Six that Gerber found dating the comic "very overwhelming."

"Pete has a certain M.O. and he’s very intense to his girlfriends," the source added.

Davidson himself has made similar admissions. In a 2020 interview with Charlamagne Tha God, the "Meet Cute" actor described himself as "a lot for certain people."

“I cry a lot. I get into deep conversations. I care about, like, your s—t. … I like to like meet your family and know who you are."

Of course, Davidson has been transparent about his own vulnerable state in a lot of his past relationships. Just like the women he has dated, he has his own traumas and his dating habits don't necessarily indicate malicious intent. 


However, given the track record, the proverbial high-fives Davidson receives every time he steps out with another woman who is coming out of a tumultuous past relationship ought to be carried out with caution.

RELATED: 5 Rules Pete Davidson's Girlfriends Allegedly Had To Follow While Dating Him 

Alexandra Blogier is a writer on YourTango's news and entertainment team. She covers celebrity gossip, pop culture analysis and all things to do with the entertainment industry.