During the 2014 MTV Video Music Awards, they were caught on camera holding hands backstage, sparking rampant speculation that that they’re a couple. Check out a timeline of Ariana and Big Sean’s relationship. Brooks and Grande’s relationship began in 2012 when Brooks and his twin brother Luke, two members of the Australian boy band Janoskians, competed in a contest for who could get Grande’s attention first.
They even shared a smooch on stage at the Power 106 Powerhouse Concert on June 6. She met Graham when the two were teenagers starring in Broadway musical 13 that year. The pair dated for three years, before calling it quits in 2011. Since then, they’ve been on friendly terms, with Graham attending a few of Ari’s concerts. He didn’t cheat or anything, they just found it difficult to make it work. But it seems they’ve been IG official for quite some time, since Dalton’s been posting about quarantine on his private account, @dalton_jacob.
Ariana and Sean met two years before getting romantically involved while collaborating on music in 2012. To learn more about Big Sean’s complete dating history, scroll through the gallery below. Naya is commonly regarded as Sean’s most serious relationship, as the pair nearly got married in 2014 before deciding to call off their nuptials. According to the former Glee actress’ 2016 memoir, Sorry Not Sorry, she and Sean weren’t the best fit. “He is the type of guy she has been looking for,” a source exclusively told Us in August.
It was a simple black and white photo of Mac looking up at her. At the end of the video, Ariana and Dalton can be seen sweetly dancing together, hugging, and kissing in what looks like a bedroom. That was pretty huge for the couple, since it was their first sign of ~official~ relationship status.
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She and Big Sean reportedly started dating sometime after that. They broke up in late 2018, but it wasn’t confirmed until early 2019 — when Big Sean was spotted with Grande. After Big Sean’s relationship with Naya Rivera ended in April 2014, she got married to her longtime friend Ryan Dorsey in July 2014 and you might have wondered how Big Sean was dealing with that situation.
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The contest led to the trending Twitter hashtag #JaiVsLukeForAriana, which caught the attention of Grande’s mom, who showed her daughter the boys. Grande then messaged Brooks her phone number and the two began dating a few months later. After two months of phone and Skype calls, the two met in person for the first time in January 2013, which Grande documented in a video.
The former “Victorious” actress wasted no time at all finding herself a new man and began dating rapper Big Sean in October 2014. But things were short-lived for the artists and four months later they broke things off. Despite their toxic relationship being put out on full display, Grande and Brooks briefly got back together in May 2014, only to, unsurprisingly, breaking up for good four months later, according to Us Weekly. From dating rappers like Big Sean and Mac Miller to seeing comedian Pete Davidson, Grande certainly doesn’t have a type. However, after a matter of months of being engaged, Ariana and Pete split and Pete even deleted his Instagram account fuelling the rumours that it hadn’t ended on good terms.
Shortly after the break up, rumors began to spread about Grande dating Big Sean. The couple’s first sighting together was backstage at the VMAs when they were caught holding hands. The couple were also reportedly seen at The Grove in Los Angeles recently, getting intimate while watching a movie. The two attended the 2021 Grammy Awards together, where they were both nominees, and have most recently appeared together in the music video for Jhene’s latest single Tryna Smoke. After signing with Kanye West’s label, Big Sean released a number of mixtapes before releasing his debut album Finally Famous in 2011, which went platinum. Big Sean had fans questioning his relationship status after he was pictured with ex-girlfriend Ariana Grande as, until recently, the rapper was dating Jhene Aiko.
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After performing and accepting her award for Best Pop Video, the 21-year-old star runs backstage and she’s greeted by Sean. When she trips and stumbles in her excitement, he’s there to pick her up and hold hands. In October, unblock flirthookup 2013, Ariana debuted her visuals for “Right There,” and she went with the elaborate Shakespearean story line. Unfortunately, Sean didn’t play the Romeo to her Juliet at that point, but just look how quickly things changed!
In one photo from the evening, Sean is seen with his arm wrapped around her affectionately. “I share about one percent of my whole being with the internet,” Jhené explained to Essence in an interview at the time. A press release from Def Jam referred to the album as “the story of the highs and lows of a relationship, with insights into conflict, memories, love, sex, and more.” After cancelling his wedding to Glee star Naya Rivera, Big Sean and Ariana began dating in 2014, making their couple debut on the red carpet of the MTV VMAs. The day after his death on September 7, 2018, she posted a tribute to the rapper.
Yes, it’s true — her left tricep was now occupied by a sketch of Sean smiling and sporting a tuxedo and bowtie. If that doesn’t prove her feelings were running deep, I don’t know what will. In an interview with Billboard shortly after they launched TWENTY88, Sean and Jhené opened up about their relationship — and their statements definitely gave shippers hope. “It was pretty obvious after a while it was a date,” Jhené revealed to Flaunt Magazine.
Ariana’s relationship with Big Sean first gained media attention when they entered holding hands at the Grammy Awards in 2015. Big Sean banged up a romance with Ariana after his divorce from Naya Rivera in 2014. There was a verbal fight between the fans of the couple due to the rumors that Jai didn’t support his girlfriend during her grandparents’ death.
Sadly, by the time Jhené was finally single again, Sean no longer was. The next day, photos were published on a blog calling Jhené “Sean’s new Spanish girlfriend,” so she tweeted, “I’m not dating Big Sean LOL.” As they say, good things come to those who wait — and despite poor timing getting in the way of Sean and Jhené’s connection, they finally found their way back to each other in 2016. Since then, there’s been a few bumps but also many beautiful moments along the way. Here’s a deep dive into the legendary love story that is Big Aiko. Diehard Ari fans will remember her ’ship with backup dancer Ricky Alvarez from the infamous #Doughnutgate video, in which Ari licked fresh doughnuts at a California bakery in 2015.
In case you’re wondering what the cutest Valentine’s Day ever looks like, here are Sean and Jhené posing in front of the Magic Castle in matching Mickey Mouse sweatshirts. Jhené revealed in her IG post with this photo that it was Sean’s first trip to Disneyland, which made it an extra momentous occasion. They even got a couple’s caricature done, and TBH, it’s pretty impressive. Spending NYE with someone is kind of a big deal — not only because there’s always the potential for a midnight kiss, but also because the person you choose to kick off a new year with is usually pretty special. So, when Jhené posted a pic to her Instagram Story that shows them making silly faces at Jay-Z and Beyoncé’s New Year’s party, fans understandably freaked out. When Sean and Jhené showed up to Diddy’s legendary 50th birthday bash, they definitely looked like a couple — and they stayed by each other’s sides most of the night.
