Comedian and actor Pete Davidson is not your typical leading man. Gangly, tattooed, and equipped with a world of baggage, this self-deprecating star of SNL is unapologetically himself—and women can't seem to get enough of him. From Ariana Grande to Kim Kardashian, he's dated some of the most beautiful women in the industry.
1. The Calm Before The Storm
In 2015, Pete Davidson started dating the comedian Carly Aquilino—but with his celebrity still in its infancy, his love life wasn't making headlines...yet.
2. His First Taste Of Drama
The couple had a seemingly amicable breakup—and in 2020, Aquilino appeared in 2020's The King of Staten Island, which is loosely based on Davidson's own life. But of course, the internet finds ways of digging up controversy.
3. She Had Something To Say
Many believed that Aquilino had something to say about Davidson's 2018 engagement to superstar Ariana Grande. She posted a screenshot to Instagram that read, "I know I’m the 9 billionth person to text you today about this, but… I can’t."
4. He Dated A Famous Daughter
In 2016, Davidson embarked on a two-year relationship with the daughter of acclaimed comedian Larry David—Cazzie David. But there was one thing that prevented the couple from going the distance.
5. He Kept Her At Bay
Although Cazzie confessed that she and Davidson shared a mutual infatuation, she also revealed that she "struggled to convince him that she really loved him." They called it quits—but the drama had only just begun.
6. She Regretted Dumping Him
Apparently, after they separated in 2018, Cazzie had some real regrets. She couldn't resist reaching out to Davidson, but when he finally texted her back, his response was brutal.
7. His Text Message Was Brutal
Davidson really put the nail in the coffin when he texted Cazzie that he was "happier than he'd ever been." Ouch. And the hits just kept coming.
8. His Ex-Girlfriend Hated The Attention
Davidson's next relationship was so gossip-worthy, it threw Cazzie back into the spotlight—and she hated the attention. She later admitted, "...there’s nothing that’s gonna be worse than what I already experienced with that." And what did she mean by "that"?
9. He Had A High-Profile Romance
Enter: Ariana Grande. Only a day after dumping Cazzie via text message, Pete Davidson and Ariana's Grande's romance went public.
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10. He Made It Instagram Official
On his Instagram account, which has since been deleted, Davidson posted a photo that had fans freaking out: He and Grande dressed up in Harry Potter robes. His caption read, "The chamber of secrets has been opened." Grande's response was incredibly suggestive...
11. She Really Went There
Only feeding the fire and confirming the rumors, Grande commented on Davidson's post, "u tryna slytherin (i'm deleting my account now)." This was only the beginning—but it was already doomed to a messy end.
12. He Was The Rebound King
You see, both Davidson and Grande were rebounding hard. Each of them had just ended long-term, serious relationships, with Grande breaking up with Mac Miller just before Davidson split with Cazzie David. So, how did these two even get together in the first place?
13. She Crushed On Him For Years
As it turns out Ariana Grande had a burning crush on Pete Davidson for years. Back in 2014, the two met on SNL when Grande was a musical guest, and then again in 2016, when she hosted the show. Their meeting must have left quite the impression, because once they started dating, Grande confessed everything.
14. She Foresaw Their Engagement
Ariana Grande told Jimmy Fallon, "I'm not a crush-y person, I don't have, like, crushes on people I don't know. But I left [Davidson's writing room at 'SNL'] and I jokingly said to my tour manager, I was like, 'I'm marrying him. A hundred percent.'" Little did she know, her early instincts were WAY more prophetic than she realized...
15. He Didn't Believe It
In early May 2018, Grande's manager, Scooter Braun, helped introduce her to Davidson. Backstage at SNL, Braun told Davidson that Grande had a deep-seated crush on him. He couldn't believe it.
16. They Had An Awkward Meet-Cute
The night Davidon and Grande finally came together was a little bit awkward, to say the least. He visited her apartment, where she was hosting a hangout with some mutual friends. When Davidson walked in, he said he had "zero expectations." Well, he was about to get a lot more than he bargained for.
17. He Paled In Comparison
Dressed in only a sweatpants and T-shirt, Pete Davidson came face to face with the flawless Ariana Grande, who had just come from the Met Gala. She was still decked out in her unforgettable Sistine Chapel dress.
18. He Almost Left The Party
For Davidson, he still couldn't believe that Grande was into him, even asking a friend if he should leave the party, stating, "She hates me right?" Well, one thing's for sure: She did not hate him...
19. He Wasn't Smooth
Before long, Davidson found himself playing a game of Quiplash with his stunning host and 10 other friends. But after two hours of fun and games, he was ready to get serious. However, it didn't go as smoothly as he'd planned.
20. He Made His Move
In an interview with Howard Stern, Davidson revealed that he's not the best charmer around, especially when it came to making his move with Grande: "I literally was like, 'Hi, can I kiss you please?' We played the game, everybody left, and then it was just me and her. And I was like, 'Well, if there was ever a shot, it would be now. Go for it.'"
21. He Wanted To Marry Her Immediately
Davidson and Grande moved fast. Apparently, right after meeting her, the comedian began shopping for a ring. He contacted jeweler Greg Yuna with his ring request and told him to keep it a secret. Yuna had no clue who the ring was actually for. But soon the entire world would know.
22. They Used Social Media To Announce It
Although rumors of their relationship had been circling for a couple of weeks, on May 30, Davidson announced his relationship on Instagram. Fans didn't have to wait long for more. The next day, Grande took to social media with her own gushy post.
23. They Didn't Shy Away From PDA
Grande posted an adorable couple photo: Davidson holding her in a loving embrace. But it was the caption that sparked even more rumors.
24. The Caption Was A Clue
Grande's caption read, "i thought u into my life ???? woah ! look at my mind," and it turned out to be a lyric from one of her unreleased songs from the album Sweetener. The song was all about Davidson. In fact, she didn't even try to hide it...
25. She Wrote Him A Song
Grande immortalized her relationship with Davidson by writing the song, "pete davidson." Unfortunately, for this happy couple, however, not everyone was thrilled with their relationship status.
25. He Struggled With His Mental Health
Before they'd even made it official, Davidson and Grande faced backlash. Many believed that because of his mental illnesses, he shouldn't be dating at all. As a result, he made a post so heartbreaking—it's unforgettable.
26. He Defended Himself On Social Media
To combat the trolls, Davidson took to his Instagram story and defended himself, with part of his post reading, "just because someone has a mental illness does not mean they can't be happy and in a relationship."
27. She Inspired His Tattoos
Davidson didn't let the haters get in the way of dating Grande. In fact, he even expressed his devotion to the pop star by adding some Grande-inspired tattoos to his collection: the bunny mask from her Dangerous Woman album on his neck, and a tell-tale "AG" on his thumb.
28. He Proposed
During her performance at Wango Tango, Grande was photographed with some new bling on her ring finger. Although barely anyone caught on, this couple had already taken things to the next level.
29. The Ring Was Enormous
The custom engagement ring Pete Davidson gave Ariana Grande did not come cheap. TMZ reported that it cost him almost $93,000.
30. They Commented On Each Other's Posts
Davidson and Grande's whirlwind romance was obviously mirrored in their explicit social media comments, captions, and photos—but his official engagement reveal might have been the sweetest post yet.
31. He Announced It To The World
On June 15, 2018, Davidson posted a subtle black and white photo of their overlapping hands—his new fiancé's gigantic pear-shaped diamond glinting for all to see. His romantic caption read, "u know what you'd dream it be like ? it's better than that," and she responded, "so much better." Swoon.
32. He Moved Into Her Lavish Apartment
Mere weeks after going public with their love, Davidson and Grande were engaged and moving in together—and their digs were downright resplendent. The comedian confirmed that they shared a Manhattan apartment that Grande had bought for a whopping $16 million.
33. He Joked About Their Relationship
Forever the joker, Davidson quipped about his new digs in a GQ interview: "She's really sweet. She's like, 'This is our house,' and I'm like, 'You're very nice for saying that. Thank you for letting me stay here." Very much swept up in the honeymoon phase, Grande had a lot more to give her new man.
34. Her Tattoos Shocked Everyone
When it came to Pete Davidson, Grande made a very risky decision. Just as he'd gotten tattoos in her honor, she went out and did the exact same thing for him. She got a tattoo reading "REBORN" which matched Davidson's, as well as a very delicate one on her ring finger that simply read "Pete." But that wasn't the most shocking tat of all.
35. Fans Noticed Something Unusual
While the couple was out galavanting in NYC, fans quickly spotted some new ink on Grande's foot. It read "8418"—a number incredibly important to Davidson, and for one heartbreaking reason.
36. She Paid Tribute To His Father
"8418" seemed to be a nod to Davidson's late father as it was his father's badge number. As a firefighter, Scott Davidson had tragically passed on September 11, 2001. But that wasn't all.
37. He Gave Her His Father's Badge
Davidson and Grande already had matching "8418" tats in memory of his father, but he was about to take this gesture one step further. He presented Grande with his father's actual firefighter badge—the one he'd passed in—and the backlash was unreal.
38. They Enraged The Public
Davidson posted a photo of Grande wearing his father's badge like a necklace and the consensus wasn't pretty. Many people found this to be utterly disrespectful. Faced with vicious criticism, the comedian shared his side of the story.
39. He Proved His Love
Davidson defended his choice to give Grande his father's badge by expressing his love for her. He also said, "My dad would be so happy and love her so much." But if you think that this was the end of the necklace drama...it wasn't.
40. The Fans Figured It Out
Some very observant fans began speculating that Davidson had given his father's badge to his ex-girlfriend, Cazzie David. And as it turns out, he did. Once again, he took to Instagram to set the record straight.
41. He Gave Her The Real Thing
According to Davidson, he'd had many replicas of his father's badge made—one of which he'd given his ex. However, the real badge was the one he'd given his fiancée: "The one that Ari has is the one my dad actually died in and the one he wore his entire career and the one I've worn for over 17 years. I've actually never taken it off other than for SNL or for work. So it means a lot to me."
Unfortunately, all of this social media criticism was just too much for the comedian—and it pushed him into making an extreme decision.
42. He Deleted All Of His Instagram Posts
Davidson's fans were shocked when they visited his Instagram profile, only to find all of his posts completely erased. This sent everyone into a speculative frenzy, but the truth was terribly disheartening.
43. He Lashed Out
Davidson's reason for deleting his social media became hauntingly clear when he shared that "the internet is an evil place and it doesn't make me feel good."
44. They Were All Over Each Other
Besides the fraught social media landscape, Davidson and Grande seemed like the picture of giddy young lovers, even making their first red carpet appearance as a couple at the MTV Video Music Awards. But little did they know, they were racing toward their inevitable end.
45. She Lost A Lover
In September, tragedy struck. Grande's ex-boyfriend Mac Miller passed and it left the singer completely wrecked with grief. Unfortunately, this changed everything.
46. He Knew It Was Over
In a 2020 interview, Pete Davidson confirmed that Miller's untimely passing sparked the beginning of the end: "I pretty much knew it was over after that."
47. They Avoided The Spotlight
In the weeks that followed Miller's passing, Davidson and Grande kept a low profile and failed to attend the Emmys. Behind the scenes, their relationship was completely falling apart.
48. He Covered Her Up
In mid-October, Davidson was spotted at Yankee Stadium with his bunny-ear tattoo covered by a heart—a small 'a' next to it. Well, eventually, even that tiny 'a' got covered up with an even tinier heart. The writing was on the wall. Davidson and Grande were over.
49. They Called The Engagement Off
On October 14, Davidson and Grande's split was officially confirmed. The comedian began covering up the rest of his Grande-inspired tattoos. But when it came to who broke up with who, both parties had a different story to tell.
50. They Had Different Stories
Ariana Grande claimed that before the breakup, she and Davidson were "up and down and on and off." Meanwhile, during one of his stand-up performances, the comedian bluntly said that he'd been "dumped." But even though the split was official, the drama still wasn't over.
51. He Joked About The Breakup
To nobody's surprise, Davidson used his failed engagement as comedic material. So, when he decided to joke about it during an SNL promo, it really got under Grande's skin...
52. She Didn't Take It Lightly
In the SNL promo, Davidson pretends to propose to musical guest Maggie Rogers who immediately rejects him. He looks into the camera and says, "0 for 3." Grande must have seen this little joke because, hours later, she took to Twitter to give him a piece of her mind.
53. She Deleted Her Tweet About Him
Grande bit back at Davidson's jokes by tweeting out, "for somebody who claims to hate relevancy u sure love clinging to it huh." She has since deleted the tweet.
54. She Said "thank u, next"
Although this relationship seemed to leave a bitter aftertaste, the song "thank u, next" positively addresses Davidson: "Even almost got married / And for Pete, I'm so thankful." Even so, it was about to get dark.
54. He Erased His Social Media
On December 15, 2018, Davidson deleted his Instagram account after getting involved in an online squabble between Ariana Grande and Kanye West. However, the last message he posted was extremely worrisome.
55. He Posted A Disturbing Message
Ariana Grande freaked out after reading Davidson's last message: "i really don't want to be on this earth anymore. i'm doing my best to stay here for you but i actually don't know how much longer i can last. all i've ever tried to do was help people. just remember i told you so." She tried to contact him and see him, but he wanted nothing to do with her.
56. He Moved On
For Pete Davidson, 2019 was a fresh new year. It was time to leave all the heartache of 2018 in the past—and with a new chapter came a brand new line-up of girlfriends. First up? Kate Beckinsale.
57. He Met Her At An After-Party
In January 2019, Davidson met Beckinsale at the Golden Globes after-party. They were seen flirting and eventually left the function together, sparking some fresh rumors.
58. He Couldn't Deny It
Only days later, the comedian made a subtle nod to his new flame. According to Us Weekly, one of the audience members screamed out Beckinsale's name. Apparently, Davidson beamed and simply said, "yes."
59. She Weighed In
By February, the couple had been photographed together on multiple occasions. Reporters were eager to get their claws into this sensational duo and even approached Davidson's ex, Ariana Grande, for her opinion on the new couple.
60. His Ex-Fiancé Approved
When TMZ asked Ariana Grande for her take on Davidson and Beckinsale, her reply was approving and warm: "So cute!"
61. They Made Out In Public
In early March, the couple publicly confirmed their romance by making out a New York Rangers hockey game. But not everybody was happy about it.
62. He Was 20 Years Younger Than Her
Fans and critics instantly honed in on the 20-year age gap separating Davidson and Beckinsale. To the rest of the world, their relationship seemed somewhat unconventional. But the two of them were far more serious than people realized.
63. She Introduced Him To Her Parents
In mid-March, Beckinsale and Davidson had dinner with her mother and stepdad. However, this wasn't their usual fun night on the town. This was the anniversary of her father's passing. It seemed serious—but sadly, this romance already had an expiry date.
65. She Kept Her Lips Sealed
Unlike Davidson's ex-fiancé, Beckinsale refrained from talking so openly about her relationship—and the one time she did, she didn't even mention her beau's name. However, it was so obvious who she was talking about...
66. She Finally Opened Up
In an interview with the Los Angeles Times, Beckinsale talked about how she'd never had to deal with so much media attention: "I've never been in this position before—never dated anybody who comes with their own bag of mischief. It’s all quite shocking, and something to get used to. I think if you liked the person less, you would bow out of it. If that were the main thrust of the relationship, there would be a problem. But it’s not."
67. It Was Short And Sweet
Well, as promising as these two seemed, this whirlwind romance came to an abrupt halt. By mid-April, Davidson and Beckinsale had amicably called it quits.
68. He Had A Summer Fling
Following his springtime heartbreak, Pete Davidson had the summer to look forward to, especially when it promised a fling with the stunning Margaret Qualley.
69. He Kept It Quiet
It really seemed as though Davidson had learned his lesson from his explosive romance with Ariana Grande. He and Qualley kept their fling private. Still, their romance was incredibly short-lived. Although they were spotted in September, enjoying a date night in Venice, the couple had split by October.
70. He Dated A Model
Only a month later, Davidson dove into another romance with another beautiful woman, model Kaia Gerber. But it was doomed from the beginning.
71. His Demons Ruined Everything
Later, Davidson confessed that during his time with Gerber, he had grappled with a lot of personal baggage. He said in an interview that he was "going through a lot." Although he managed to keep this relationship low-key, he did have one incredibly loving thing to say about his model girlfriend.
72. He Sang Her Praises
Davidson only had positive things to say about Kaia Gerber, stating that she was "beautiful, smarter than me…If anyone was worried that I was too smart or advanced for her, they do not have to worry at all. She was way, way smarter than I was."
73. He Seduced The Star Of Bridgerton
Pete Davidson soared into 2021 and almost immediately found his next flame—the up-and-coming star Phoebe Dynevor, who'd just made it big on Bridgerton.
74. He Visited Her Hometown
On March 21, Davidson and Dynevor were seen hanging out and looking rather intimate in her hometown of Altrincham, Greater Manchester. While romance rumors swirled, they never made their relationship official. After all, there was one huge obstacle that prevented their love from taking flight.
75. They Couldn't Handle The Distance
Although the couple was spotted kissing at Wimbledon in July 2021, they were over by August. You see, it was destined to be a long-distance relationship—something neither one of them could overcome.
76. They Had Instant Chemistry
Fast-forward to October 2021, and Davidson meets one of the most famous women in the world—Kim Kardashian. It was quite the interlude. Not only did Kim host SNL, but she and Davidson also shared a smooch during their sketch. Little did anybody know, this was the beginning of something big.
77. Their Hand-Holding Sparked Rumors
Not long after, Davidson was spotted out with Kim, Kourtney, and Travis Barker at Knott's Scary Farm. Everyone assumed they were just friends, but a snapped photo of Davidson and Kim holding hands on a rollercoaster had the rumor mill rolling.
78. She Invited Someone Special To His Party
In November, Kim Kardashian helped organize a very special birthday for Davidson. Knowing how much of a fan he was of Flavor Flav, she invited the rapper to the festivities. Flavor Flav later admitted, "I was the birthday gift." Unfortunately, there's at least one downside to Davidson and Kim's relationship...
79. She Came With Baggage
Kim Kardashian's ex-husband isn't pleased with her relationship with Pete Davidson—and has publicly tried to get Kim back on multiple occasions. At one of his concerts in December, he even asked her to "run right back" to him. And that isn't all.
80. Her Ex Doesn't Like Him
According to Entertainment Tonight, Kanye even dragged Davidson and Kim in one of his recent interviews: "How you gonna bring me to SNL and kiss the dude you dating right in front of me?" Of course, Kanye's bitterness doesn't end there.
81. He Feels Threatened
With his jealous behavior, it's no wonder that one of Kanye's leaked songs includes a lyric about how he wants to hurt his ex-wife's new boyfriend, Davidson. Allegedly, the scary lyrics have prompted the comedian to amp up his personal security...just in case.
82. They're Happy Together
Despite the negativity and the mounting Kanye drama, Davidson and Kim's relationship seems to be heating up nicely. Although Kim's home life is full of chaos, she and Davidson escaped from it all at the beginning of 2022.
83. They Ran Away
Davidson and Kim jetted off to the Bahamas for a much-needed getaway, and fans went wild after her latest sultry Instagram post.
84. He Might Be The Mystery Photographer
In one of her epic bikini shots, the shadowy silhouette of the photographer can be seen, and many believe that it's Davidson himself. Fans are starting to think that it won't be long before Kim makes the relationship Instagram official.
