Before Dalton Gomez, Ariana Grande Probably Said “Thank U, Next” to These Guys

Ariana dated the Riverdale actor for almost three years after meeting on the set of their 2008 Broadway musical 13. The two have remained friends since then, and Graham even defended Ariana during her #Doughnutgate scandal in 2015. “I think the whole thing is hilarious,” Graham told People at the time. “She’s such a sweet girl. It’s tough. We all say things that we regret. I don’t think it speaks to her character at all.”

Ariana moved on with The Wanted singer shortly after, and the two dated for four months in 2013. The couple even collaborated on Ariana’s song “Almost Is Never Enough.” It’s unclear what went wrong, but in February 2014, Ariana confirmed in an interview that they had split. “We broke up a little while ago, but he’s a really good friend,” Ariana said. “He’s so talented. I am so glad to have met him and have a friend like him in my life. He’s an amazing person. It was very civil. It was mutual.” In 2016, they collaborated again, only this time it was for Nathan’s song “Over and Over Again.”

Big Sean struck up a romance with Ariana after calling off his wedding to Naya Rivera in 2014. The pair made their public debut as a couple when they were spotted holding hands at the MTV VMAs, and the singer even made a cameo in Big Sean’s “Patience” video.

However, eight months later, Ariana and Big Sean called it quits in April 2015. “They both deeply care for each other and remain close friends,” their reps told Us Weekly in a joint statement. “We kindly ask that the media respect their wish for privacy regarding this personal matter at this time.” While neither Big Sean nor Ariana ever revealed the reason for their breakup, sources said “they made the decision to part ways because of their conflicting touring schedules.”

Three months later, Ariana was linked to her backup dancer after they were shown kissing in Ariana’s now infamous #Doughnutgate video. Ariana and Ricky dated for a year before parting ways in July 2016. “She broke up with him. He didn’t cheat or anything, they just found it difficult to make it work. They are still friends though,” a source told E! News at the time. “[She] is happy to be single and do her for a little while.”

Still, it wasn’t very long until rumors that she was dating Mac Miller began swirling. The pair initially started off as friends and collaborated on music together, but in August 2016, the duo were spotted kissing during a romantic sushi date in Encino, CA. There were also rumors that the couple might have gotten engaged after Ariana debuted a diamond sparkler on her ring finger during her Manchester concert in June 2017.

Neither Ariana nor Mac ever confirmed the reports, but by May 2018, the pair had gone their separate ways. “Hi! This is one of my best friends in the whole world and favorite people on the planet Malcolm McCormick,” Ariana wrote on Instagram, confirming their split. “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! Unconditional love is not selfish. It is wanting the best for that person even if at the moment, it’s not you.”

Sadly, Mac died from an accidental drug overdose at age 26 in September 2018.

Ariana moved on with the Saturday Night Live star in May 2018, and they got engaged a few weeks later. However, their romance was short-lived as they broke up in October 2018. According to People, they split after realizing “it was way too much too soon.” Ariana later referenced the breakup in her Mean Girls-inspired “Thank U, Next” music video, where she dedicated a page in her burn book to Pete. His page read: “I love u always” and “Sry I dipped.”

Rumors of a romance between Ariana and Mikey first began swirling in August 2019 when they had a steamy makeout session in the singer’s “Boyfriend” music video. The two were then spotted hanging out together on multiple outings, and Mikey even joined Ariana on her Sweetener world tour with his band, Social House. It wasn’t until a month later, though, that Ariana’s brother, Frankie, confirmed their relationship to Us Weekly. “I love Mikey. I think he’s a really sweet guy. So talented. So kind and so caring,” the 36-year-old told the outlet. “He’s a great guy.” However, he later backtracked in a now-deleted tweet, saying Ariana is single. In February, though, they were spotted walking arm in arm at Disneyland, but they broke up days later.