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. 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.
The couple — who collaborated on her 2013 single “The Way” and his 2016 single “My Favorite Part” — took their romance public in September 2016 when Grande took to Instagram to share a photo of her and the rapper hugging on the floor with the caption “baabyyy.” After years of a very loving relationship, PEOPLE confirmed in early May 2018 that the pair amicably split a few weeks prior.
Just one month before their split, Miller Tweeted his support for Grande when she released her first single since the Manchester bombing in May 2017: “very proud of this girl right here. Welcome back. We missed You. One of a kind.”
Miller tragically died of an accidental drug overdose in September 2018.
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 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 theatre. 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 gushed 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 the effort Brooks put in Tweeting her and making a video for her explaining why she should date him in July 2012, Grande couldn’t say no. Grande and Brooks split in August 2014 after dating for nearly 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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