A look back. Ariana Grande’s dating timeline includes more famous boyfriends than just Pete Davidson, Mac Miller and Big Sean. Grande has been around in Hollywood for more than 15 years. She made her Broadway debut in 2008 in the musical 13 before her move to TV 2010 as Cat Valentine in Nickelodeon’s Victorious.

However, music is where Grande really shined. Though she released her first single, “Put Your Hearts Up” in 2011, Grande didn’t shoot to pop stardom until 2013 when she released her single “The Way” with ex-boyfriend Mac Miller. After that, Grande released hit after hit with songs like “Bang Bang,” “Dangerous Woman” and “No Tears Left to Cry” before her first-ever number-one single in 2018 with “Thank U Next” following her breakup from Pete Davidson.

Like most celebrities of her star power, Grande’s relationships have been reported on quite a bit. “Love is a really scary thing, and you never know what’s going to happen. It’s one of the most beautiful things in life, but it’s one of the most terrifying. It’s worth the fear because you have more knowledge, experience, you learn from people, and you have memories,” she told Seventeen in 2014. We know the mainstays of her love life (a.k.a. Davidson, Miller and Big Sean) but what about her boyfriends in between? Ahead, we looked back at Ariana Grande’s dating timeline and relationship history, from her engagements to the breakups we’ll forever remember.

Graham Phillips (2009–2011)

Best known for his role on CBS’s The Good Wife, Phillips was Grande’s first famous boyfriend. The two met in 2008 when they starred in the Broadway musical 13 (where Grande had her first kiss) together when they were teenagers. After remaining friends for a year, Phillips and Grande began dating. After three years of dating—including an appearance at the 2010 Emmys together and several duets—the two amicably split in December 2011. Five years after their breakup, they reunited in July 2016 for a 13 cast reunion for.

Jai Brooks (2012–2014)

Source: Instagram

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. 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.

They continued dating long distance for a while, with the two flying back and forth between Australia and America, until the end of 2013 when Grande accused Brooks of breaking up with her over text in an interview with Complex. Shortly after, Brooks responded in a tweet, accusing Grande of cheating on him with Nathan Sykes, her duet partner. After a few months apart, the couple reunited at the beginning of 2014 and dated for around six months until they quietly broke up again.

Nathan Sykes (2013)

In the five-ish months that Grande and Brooks were broken up, the singer dated Sykes, one-fifth of the British boy band the Wanted. Grande first saw Sykes on a red carpet in early 2013 (“I saw him on a red carpet, and we locked eyes with each other all night. I thought he was cute as hell. Nothing happened obviously,” Grande told Entertainment Wise), but they didn’t properly meet until months later when they filmed the music video for their song “Almost Is Never Enough.”

After the singers reconnected as opening acts for Justin Bieber’s Believe tour later that year, they began dating. The two dated for about five months until they broke up at the beginning of 2014 due to the strain of dating long distance. There were no hard feelings, however, as the singers reunited as friends in 2016 to sing the duet “Over and Over Again” for Sykes’s debut solo album.

Big Sean (2015)

Grande’s next public relationship came in 2015 when she began dating rapper Big Sean. The two first met in 2014 when they collaborated on Grande’s song “Right There” from her debut album Yours Truly. After months of dating rumors (including about Grande’s getting into her first car accident on the way to Big Sean’s house), the two made their official debut as a couple at the 2015 Grammys. After eight months of dating, including Big Sean’s surprise appearance on Grande’s The Honeymoon Tour to perform “Best Mistake” and “Right There,” the two called it quits in April 2015. According to a source for E! News, the breakup was over conflicting schedules. Both artists planned to be on tour for the next year, which would make it hard for them to be together.

Ricky Alvarez (2015–2016)

Grande and Alvarez’s relationship was short-lived and not known by many of her fans—until Doughnutgate, the singer’s 2015 scandal in which she was videotaped licking a doughnut that she didn’t buy and calling America “fat.” The video also happened to feature Alvarez, one of Grande’s backup dancers, whom she was dating at the time. The two first sparked rumors when they kissed onstage for the first time at a 2015 Pride festival in June. Grande and Alvarez dated for about a year until July 2016 when Grande tweeted cryptic thoughts about “change” and liked fans’ tweets speculating that the two were no more and that Alvarez somehow did Grande wrong.

Mac Miller (2016–2018)

Miller, perhaps Grande’s most high-profile boyfriend before Davidson, and Grande go way back to 2012 when they recorded a cover of “Baby It’s Cold Outside,” which Grande posted on her YouTube channel. A year later, Grande released her debut single, “The Way,” featuring Miller. Though the music video for “The Way” featured a romantic kiss between Grande and Miller, the singer has denied that the two were romantically involved at the time, claiming that the kiss was scripted and the two were friends.

In 2016, four years after the release of their song, Grande surprised fans when she was seen kissing Miller outside a sushi restaurant in Los Angeles. After that, Grande was featured on Miller’s song “My Favorite Part” and directed an unreleased music video for her beau’s song, “Dang.” Miller also joined Grande on her tour in 2017 to duet “The Way” with her. The couple announced their breakup in May 2018. Though neither has revealed the reason for the breakup, Grande responded to fans on Twitter, calling her previous relationship “toxic” and “scary.” In September 2018, Miller died from an accidental drug overdose at the age of 28. In an interview with Apple Music in May 2020, Grande opened up about how Miller’s musicality inspired her. “I think that nothing mattered more to him than music, ever,” she said. “And he was the kind of person who woke up and rolled into the studio, tumbled out of bed, into the studio next door. Nothing was more important. Talk about losing track of time and forgetting to eat, remind yourself to take care of yourself and be a person. He was a person who gave literally every single second of his thought and time and life to his music.”

Pete Davidson (2018)

Grande’s relationship with Davidson is still evolving and might be her last. However, here’s a brief overview: The two met in 2016 when she performed on NBC’s Saturday Night Live, of which Davidson is a cast member. They didn’t begin dating until May 2018, the same month that Grande confirmed her breakup with Miller, and news broke that Davidson and his then-girlfriend, Cazzie David, had split. After two months of dating, Davidson confirmed that he and Grande were engaged in June 2018 on an episode of The Tonight Show Starring Jimmy Fallon. No word yet on when the wedding will be (or if Grande will wear her signature high ponytail for the ceremony). The couple split in October 2018. Grande went on to reference Davidson and other exes in her song “Thank U Next.”

Dalton Gomez (2020-Present)

Source: Instagram

Grande first started dating Gomez, a real estate agent who represents celebrity homes, in January 2020. The “Thank U Next” singer confirmed their relationship in May in her music video for “Stuck with U” with Justin Bieber. The video saw Grande and Gomez slow-dancing. The confirmation came after speculation the two were dating from Grande’s Instagram posts, which showed her and Gomez quarantined together amid the COVID-19 pandemic. In December 2020, Grande confirmed that she and Gomez are engaged via an Instagram slideshow of photos of them together. Among the pictures was a shot of her engagement ring, which featured an oval-shaped diamond and a pearl given to her by her late grandfather. “forever n then some,” she captioned the post.

A version of this post was originally published in 2018.

from StyleCaster