Here's a complete timeline of Ariana Grande and Pete Davidson's whirlwind engagement and sudden split

Callie AhlgrimDec 21, 2020, 02:17 IST

Pete Davidson and Ariana Grande presumably met in September 2014.Neilson Barnard/Alberto E. Rodriguez/Getty Images

Ariana Grande and Pete Davidson began dating in May 2018, before either had confirmed they'd broken up with their longtime partners.
They got engaged shortly after, but split less than five months later in October.
Insider's timeline lists every milestone and revealing moment in their relationship, as well as major events and comments they've both made since their breakup.

Ariana Grande and Pete Davidson redefined the idea of a "rebound relationship" for the rest of eternity. Mere weeks after splitting up with longtime partners - and just 24 days after initial reports claimed the two were "casually dating" - it was reported and later confirmed that the two stars were engaged to each other.

Less than five months later, the couple had called it quits.

If their fast-forwarded romance has given you whiplash, here's the breakdown of everything that happened between them.

This post has been updated multiple times since its original publication.

September 2014: It's possible that Ariana Grande and Pete Davidson met for the first time.

Grande performed "Love Me Harder" with The Weeknd; Davidson was introduced as the "resident young person" on the "SNL" "Weekend Update." Ariana Grande/Saturday Night Live/YouTube

March 2016: Grande hosted "Saturday Night Live" and publicly interacted with Davidson for the first time.

Davidson and Grande onstage during the singer's opening monologue. NBC

November 2017: Davidson wore Grande's iconic "Dangerous Woman" mask for a "SNL" skit.

If this was unintentional, it's awfully coincidental. NBC / @arianagrande/Instagram

April 20, 2018: Grande posted the final photo with her then-boyfriend, Mac Miller.

The couple had been officially dating since September 2016. @arianagrande/Instagram

April 21: Davidson told the crowd during a stand-up performance he would probably marry his girlfriend.

Davidson and Cazzie David attend the 2017 MTV Video Music Awards. Christopher Polk/Getty Images

May 3: Davidson's then-girlfriend posted the final photo of the couple together.

There are no photos of David on Davidson's Instagram account. @cazziedavid/Instagram

May 7: Davidson and Grande had their first date and first kiss.

Davidson in a "SNL" sketch with Donald Glover on May 5; Grande at the Met Gala on May 7. Will Heath/NBC / Jason Kempin/Getty Images

May 9: News broke that Grande and Miller had ended their long-term relationship.

Mac Miller is the stage name of Malcolm McCormick. @ArianaGrande/Instagram

May 12: Grande and Davidson were spotted hanging out at a "SNL" after-party.

Clouds are kind of their "thing." @nctsweetener/@davidsonsource/Twitter

May 16: Davidson confirmed that he had split with his girlfriend of two years.

Peter Rosenberg and Davidson are good friends. Open Late/Complex

May 17: Davidson posted a photo that clearly showcased a new cloud-shaped tattoo.

He has multiple finger tattoos. @petedavidson/Instagram

May 17: Davidson covered up a tattoo of his ex-girlfriend.

"Did this crazy coverup last night on my boy," tattoo artist Jon Mesa captioned the photo. @jonmesatattoos/Instagram

May 18: It was officially reported that Grande and Davidson were dating.

Many fans originally responded with disbelief. Alberto E. Rodriguez/Kevin Winter/Getty Images

May 19: Around this time, Davidson commissioned a custom-made diamond ring.

Grande performing at the Billboard Music Awards on May 20. Kevin Winter/Getty Images

May 20: Davidson and Grande were spotted acting like a couple.

Davidson posted this photo - apparently taken on May 20 - for Grande's birthday on June 26. @petedavidson/Instagram

May 23: Grande called her former relationship with Miller "toxic."

Grande posted this photo on Instagram when the two were apparently still together. Ariana Grande/Instagram

May 24: Davidson hit back at people saying he shouldn't date Grande because of his mental illness.

Davidson often references mental health in comedy routines. Getty Images

Around this time, Davidson and Grande began to like and comment on each other's Instagram posts with a startlingly high frequency.

One of the more tame interactions. @petedavidson/Instagram

May 30: The couple made their official Instagram debut.

Davidson and Grande became Instagram official. Pete Davidson/Instagram

May 31: Not to be outdone, Grande followed with her own post.

A clear declaration of love. @arianagrande/Instagram

June 2: Davidson revealed a permanent homage to his new girlfriend - twice.

He didn't heed his tattoo artist's advice. @londonreese/Instagram

June 3: Grande publicly debuted her engagement ring.

The custom diamond took two weeks to make. Kevin Winter/Getty Images

Backstage at Wango Tango, Grande wore the same crewneck sweatshirt Davidson had worn six months previously.

Davidson in a photo from January; Grande backstage at Wango Tango in June. @petedavidson/Instagram / Jesse Grant/Getty Images

June 6: Grande joked about having kids with Davidson.

A screenshot captured by the eagle-eyed account @commentsbycelebs. @commentsbycelebs/Instagram

June 8: Grande and Davidson attended the "Kids See Ghosts" listening party and gave us another glimpse of the ring.

"I wasn't expecting an interview," Grande said. BigBoyTV/YouTube

June 9: Grande acknowledged that her Instagram is slowly transforming into a fan account for her boyfriend.

"we're so we're so REBORNNNNNN," Davidson commented. Instagram/arianagrande

Indeed, Grande's comment section has easily become the go-to spot for updates on Davidson's social media activity.

A selection of the recent interactions between Davidson and Grande in her Instagram comment sections. @arianagrande/Instagram

June 11: Multiple outlets reported Davidson and Grande had gotten engaged.

Fans were surprised - but also supportive. Jordan Strauss/Invision/AP; Alberto E. Rodriguez/Getty Images

June 11: The two continued their tour of affection in Disneyland.

Grande took photos with a fan at Disneyland. @arianagrandeupdatesx/Instagram

June 13: Grande's former costar Jennette McCurdy said they'd recently texted about the engagement.

The two stars were rumored to be feuding when the show ended. Ben A. Pruchnie/Getty Images

June 15: Nick Cannon claimed Davidson called him before popping the question.

Nick Cannon said he takes credit for "introducing" Davidson to the world of entertainment. Astrid Stawiarz/Getty Images

June 15: Davidson posted the official engagement ring reveal on Instagram.

The reveal was subtle, yet somehow obvious. @petedavidson/Instagram

June 16: The couple moved in together.

Fans have noticed that Grande, who has anxiety, was less bothered by paparazzi those days. Splash

June 18: Grande defended her decision to name a song "Pete Davidson" on her upcoming album.

Grande's album rollout included plenty of promo images. @arianagrande/Instagram

June 18: Grande and Davidson got tattoos in the same spot.

Grande tagged Davidson and three other friends in the video. @arianagrande/Instagram

June 18: Grande's brother gushed about their family's "big news."

The Grande siblings in 2015. Stuart C. Wilson/Getty Images

June 20: Davidson confirmed the engagement during an appearance on "The Tonight Show Starring Jimmy Fallon."

"I'm forever known as her plus one," Davidson joked. The Tonight Show Starring Jimmy Fallon/YouTube

June 25: Grande responded to "the hate and all the nonsense opinions."

They'd been stepping out together frequently. Splash

June 26: Davidson posted multiple Polaroids of the couple in celebration of Grande's 25th birthday.

Grande turned 25 in June; Davidson turns 25 in November. @petedavidson/Instagram

June 26: Grande debuted a new tattoo that matches one of Davidson's.

Grande posted this photo to her Instagram story on July 12, which clearly shows both matching tattoos. @arianagrande/Instagram

July 2: Grande reportedly got a tattoo in honor of Davidson's late father.

This is one of several tattoos Grande has. Splash News

July 5: Grande defended her fiance after he was criticized for joking about the Manchester bombing.

Grande had difficulty getting back onstage in the aftermath of the bombing. @petedavidson/Instagram

July 11: Grande debuted a new finger tattoo that appears to say "pete."

Grande already boasted several tattoos on her fingers. @nail_swag/Instagram

July 14: Davidson defended his decision to give Grande his late father's necklace.

8418 was Davidson's father's badge number. @petedavidson/Instagram

July 23: Davidson deleted all his Instagram posts after clashing with Grande's fans.

Davidson said he removed his Instagram photos and videos to avoid "negative energy." @petedavidson/Instagram

August 17: Grande released her fourth album, "Sweetener," complete with a song called "pete davidson."

In a video posted on Grande's Instagram page, Davidson said the song is "sick" and his second favorite on the album. Spotify

August 20: The couple made their red carpet debut at the MTV Video Music Awards.

Grande won for best pop video at the 2018 VMAs. Nicholas Hunt/Getty Images

September 7: Miller unexpectedly died from an accidental drug overdose.

Grande honored Miller with a touching black-and-white photo tribute on September 8. @arianagrande/Instagram

September 8: Davidson debuted a new tattoo that reads "Grande."

This is the third tattoo Davidson has commissioned that directly references his fiancee. Theo Wargo/Getty Images

September 18: The couple announced they would be taking some time away from the spotlight.

Grande also largely retreated from social media. Splash News

September 29: Davidson joked that he and Grande were going to break up during an appearance on "SNL."

Davidson on "SNL." NBC

October 10: People realized that Davidson covered up a tattoo inspired by Grande.

Davidson has several other tattoos, apparently still intact, inspired by Grande. London Reese/Instagram and Splash News

October 14: TMZ and People reported Grande and Davidson had broken up.

The two stars have reportedly split. Theo Wargo/Getty Images for Huffington Post and Alberto E. Rodriguez/Getty Images

October 18: Davidson joked about their failed engagement during a stand-up set.

Davidson often performs stand-up (pictured here in his special for Comedy Central). Comedy Central

October 30: Grande revealed new ink, which conceals a matching tattoo she had gotten with Davidson.

Grande and Davidson got the matching "reborn" tattoos in June. Jamie McCarthy/Getty Images and Ariana Grande/Instagram

November 1: Grande subtweeted Davidson after he poked fun at their engagement.

Maggie Rogers performed on the November 3 episode of "SNL," while Jonah Hill hosted. Rosalind O'Connor/NBC

November 3: Grande released a new song titled "thank u, next" - in which she explicitly names Davidson and three other exes.

The artwork for "thank u, next" references multiple media outlets that write about Grande's tweets. @arianagrande/Instagram

November 3: Davidson addressed the break-up on "SNL."

Davidson reportedly scrapped another sketch about Grande after reading her tweets. Will Heath/NBC

November 30: Davidson made an appearance in Grande's "Thank U, Next" music video.

It's unclear why Davidson's face is covered with purple markings. Ariana Grande/YouTube

December 4: Grande came to Davidson's defense after he said he was getting bullied.

"I really don't endorse anything but forgiveness and positivity," she wrote on her Instagram story. @arianagrande/Instagram

December 15: Davidson deleted his Instagram after making a worrying post and weighing in on a debate between Kanye West and his ex-fianceé.

Davidson appeared on "Saturday Night Live" just hours after posting a message that suggested he was suicidal. NBC

Since the split, Grande has described their engagement as "highly unrealistic." Davidson joked about it during a stand-up comedy special.

Ariana Grande performs during the 2019 Sweetener World Tour; Pete Davidson walks the runway at 2019 New York Fashion Week. Kevin Mazur/Getty Images / Steven Ferdman/WireImage

In early 2020, Grande began a new, more low-key relationship with Dalton Gomez. They now appear to be engaged.

Grande posted pictures wearing a new engagement ring on December 20. @arianagrande/Instagram

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