Into You: Ariana Grande's Romance Rewind — a Look Back at Her Past Loves

Grande and the Saturday Night Live actor began dating shortly after her breakup from rapper Mac Miller. On May 30, Davidson made their relationship Instagram official by posting a new photo of him and Grande posing in Harry Potter wizard robes. Grande returned the favor the following day, sharing a cuddly photo captioned, “I thought u into my life.”

And aside from showering each other with love on social media, Davidson shared a photo of his new neck ink that seemingly referenced the “No Tears Left to Cry” singer, and showed his support for her “lit” performance at Wango Tango on June 2. And on June 11, PEOPLE confirmed the stars were engaged.

 The couple — who collaborated on her 2013 single “The Way” — took their romance public in September 2016 when Grande shared a photo of her and the rapper hugging on the floor with the caption “baabyyy.” After two years together, PEOPLE confirmed in early May 2018 that the pair amicably split weeks before but will remain friends.

Just one month before their split, Miller Tweeted his support for Grande when she released her first single since the Manchester bombing: “very proud of this girl right here. Welcome back. We missed you. One of a kind.”

In July 2016, Grande and her former backup dancer called it quits after a year of dating. Though Grande and Alvarez rarely addressed their relationship, she opened up briefly about their romance for her May 2016 Billboard cover story. “We’re happy. I’m a very happy girl. I have a healthy life right now, and I think that’s all anyone cares to know. The end,” she told the trade publication.

While that may have been all she had to say in an interview, but she sure did let her lyrics do the talking: her hit “Moonlight” off her Dangerous Woman album was written about Alvarez. “I think it was after their first kiss,” Grande’s longtime friend and writing partner Victoria Monet told Billboard of the track. “He waited to kiss her for a long time, and she was really impressed. He’s such a gentleman, and the song is a great little bookmark of the start of their relationship.”

The public began to “focus” on Grande and the “Moves” rapper’s budding relationship in August 2014 when they were first spotted smooching at a movie theater. However, the pair called it quits in April 2015 after nearly nine months of dating due to a conflicting tour schedule, according to E! News. In a joint statement, the pair revealed they “care deeply for each other and remain close friends.”

Earlier that year, Big Sean appeared on On Air with Ryan Seacrest, where he spoke about his relationship with the singer. “That Ariana is very, very special. She’s very special to me,” he said. 

Before dating apps were ever a thing, Jai Brooks — an Australian YouTube comedy and member prank group The Janoskians — and his twin brother Luke challenged each other to see which one could grab Grande’s attention first via social media.

After all the effort Brooks put in Tweeting her and making a video for her explaining why she should date him in July 2012, Grande found she couldn’t say no. Grande and Brooks split in August 2014 after dating for two years.

Young love! Grande had her sights set on Sykes — a former member of boy band The Wanted — since she laid eyes on him early in her career on a red carpet, but it wasn’t until the music video shoot for their duet “Almost Is Never Enough” that sparks began to fly.

After months of speculation, both Sykes and Grande took to social media to confirm their relationship on Twitter. In January 2014, Grande confirmed in a radio interview that her and Sykes had decided to split after a five-month long relationship due to distance, but insisted that they remain close friends.

Grande and the Good Wife actor first met in 2008 when they starred alongside each other in 13: The Musical. Shortly after they had their first kiss together, the actor and the “Side to Side” singer began dating until their amicable breakup in December of 2011 after around three years of dating.


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