American singer, actress and songwriter Ariana Grande is no alien to relationships and breakups. From falling head over heels for Mac Miller to being briefly engaged to Saturday Night Live star Pete Davidson, Grande has opened up her heart to love — and heartaches.

Graham Philips

Ariana Grande with Graham Philips

The Good Wife alum met Ariana who was 15 at the time in 2008 — while they were both starring on Broadway in 13: The Musical. The pair, who jointly composed a song called “Stick Around,” dated between 2008 to 2011. Despite going their separate ways, the former soulmates reunited in July 2016 for a dinner with friends from 13.

Jai Brooks

Ariana Grande with Jai Brooks

Grande and The Janoskians star’s relationship lasted only a short time. The pair started dating in August 2012 but split barely two months after in October 2013. Brooks took to Twitter to accuse the Disney alum of cheating on him with Nathan Sykes, saying:

“Yes I was cheated on. Yes it does suck,” he wrote in a lengthy rant. “Yes I was left for another man.”

Grande, however, responded to the claims by accusing him of threatening to retaliate if she chose to leave him.

“Woke up this morning in complete and utter shock …I guess I shouldn’t be so surprised. You said to me if I didn’t come back to you, you’d make me look bad to the entire world,” she responded in a Tweet. “I’m no longer afraid of you or your lies anymore.”

Despite the row, the pair got back together briefly in May 2014 — only to break up for good in August.

Nathan Sykes

Ariana Grande with Nathan Sykes

US Weekly disclosed that The Wanted singer and Grande began dating in August 2013 after the release of “Almost Is Never Enough” from the soundtrack: The Mortal Instruments: City of Bones.

Their relationship was short-lived, however, with the pair breaking up in December of that year. A source revealed at the time that the reason behind their split was because the two “hardly ever saw each other” while another noted, “They just weren’t into it anymore.”

But, three years later, they got together once again — to jointly compose a new version of his song “Over and Over Again.”

Big Sean


Ariana Grande with Big Sean

Following months of speculation, Grande confirmed she was dating Big Sean in October 2014, calling him “one of the most amazing men in the whole world.” “It’s gotten serious very fast,” a source revealed at the time. “They are much happier than in their previous relationships.”

Meanwhile, Glee star Naya Rivera, who was engaged to the “I Don’t F—k With You” rapper before they broke up in April 2014, later alleged in her book, “Sorry Not Sorry” that she found Ariana Grande at Big Sean’s home while she and Big Sean were still together.

Grande and the “Bounce Back” rapper ended their relationship eight months later in April 2015. The “No Tears Left To Cry” singer later mentioned Big Sean in “Thank U, Next,” a single Grande released in November 2018 where she showed gratitude for her previous exes: “Thought I’d end up with Sean / But he wasn’t a match.”

Ricky Alvarez

Ariana Grande with Ricky Avarez

The backup dancer photographer and Grande were first linked in the summer of 2015 following her breakup with Big Sean. The pair had been together when the “Love Me Harder” songstress made headlines in July of that year at the time she was caught on surveillance footage licking a donut in a store and saying she “hates Americans” and “hates America.”

Although Grande told Billboard magazine in May 2016, “I’m a very happy girl,” the pair brokeup two months later. But they remained on seemingly good terms. Following the release of “Thank U, Next,” Alvarez posted a clip of himself listening to the song and Grande jokingly responded, “IM SORRY U GOT THE WORST LINE … IT WAS MEANT V LOVINGLY,” referencing her lyrics, “Wrote some songs about Ricky / Now I listen and laugh.”

Mac Miller

Ariana Grande with Mac Miller

The “Weekend’” singer and the “Dang!” rapper — got together after they collaborated on “The Way” between 2016 to 2018. US Weekly confirmed in May 2018 that the pair had broken up. A few days later, Grande opened up about their split on Instagram alongside a photo of the former flames cuddling, and she captioned it, “I respect and adore him endlessly and am grateful to have him in my life in any form, at all times regardless of how our relationship changes or what the universe holds for each of us!”

Mac Miller shared his perspective in July. “I was in love with somebody. We were together for two years. We worked through good times, bad times, stress and everything else. And then it came to an end and we both moved on,” he told Beats 1 host Zane Lowe.

“And it’s that simple.” Following the September 2018 death of Mac Miller resulting from mixed drug toxicity, Grande wrote a touching tribute to him on Instagram: “I adored you from the day I met you when I was nineteen and I always will.” Grande also paid tribute to her ex in her song, “Thank U, Next,” singing, “Wish I could say, ‘Thank You’ to Malcom / ‘Cause he was an angel.”

Pete Davidson

Ariana Grande with Pete Davidson

The Saturday Night Live star and Grande embarked on a willy-willy romance in 2018 following their respective breakups from Cazzie David and Miller. Davidson made the revelation on Instagram in May 2018 that he and Grande were dating, sharing a photo of them posing in Harry Potter outfits, which he captioned, “The chamber of secrets has been opened.”

Us Weekly exclusively revealed that the comedian and Grande got engaged about a month later, with Davidson proposing with a $93,000 diamond ring. He later told Jimmy Fallon of their plans to wed, “I feel like I won a contest, so sick. It’s f—king lit.” The pair spent the summer ‘showmancing’ their romance, which included adopting a pig and moving in together in a luxury condo in New York City’s Chelsea neighborhood.

However, five months later Us Weekly confirmed that they had broken up, with a source telling Us at the time, “They realized it happened too quick and too early.”

Davidson spoke out about their split during Saturday Night Live’s “Weekend Update” segment on November 3. “I know some of you are curious about the breakup, but the truth is, it’s nobody’s business, and sometimes things just don’t work out, and that’s OK,” he told viewers. “She’s a wonderful, strong person, and I genuinely wish her all the happiness in the world.”

Grande, on her part, in “Thank U, Next” sang that she was “so thankful” to Davidson for at one time being a part of her life.

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