1. Big Sean

Contrary to popular belief, Sean and Ariana did not turn business into romance right off the bat. The pair first met at Wango Tango in 2012, where Ariana gushed that he was "so cute" in an interview. In 2013, the pair collaborated on "Right There," a single from Grande's debut album, Yours Truly. Since then, they have collaborated numerous times on "Best Mistake," "Research," and Big Sean was the uncredited whisper on Grande's smash hit, "Problem" featuring Iggy Azalea. In 2014, the romance between the two heated up backstage at the VMAs and they made their first red carpet appearance together at the 57th Annual Grammy Awards the following year. However, their relationship came to an end due to "conflicting schedules" as they were both set to go on tour and couldn't see each other as often.

2. Ricky Alvarez

Although it was short-lived, Ariana Grande's romance with her past back-up dancer Ricky Alvarez was an impactful one For those of you who are not entirely familiar with Alvarez, or specifically when he dated Miss Grande, he was right by her side during her doughnut-licking scandal when the singer stated she "hated America." Rumors first sparked when they kissed onstage for the first time at a Pride festival in June 2015. It is also rumored that "Moonlight" and "Forever Boy" off of Grande's 2016 record Dangerous Woman were inspired by their relationship.

3. Pete Davidson

Ariana Grande and Pete Davidson were perhaps the most sought-after couple of 2018, when their whirlwind romance took the world by storm. It all happened so fast. They first met in 2016 when was the host and musical guest on NBC's Saturday Night Live, of which Davidson is a cast member. In an interview with Jimmy Fallon, Grande claims that she "always knew she was going to marry Pete" (that thought didn't age well, Ari). However, their romance didn't begin until May 2018, the same month that Grande broke up with rapper Mac Miller.

Around the same time, Davidson and his then-girlfriend, Cazzie David, had also called it quits. After only two months of dating, Davidson confirmed that he and Grande were engaged during an interview with Jimmy Fallon. Unfortunately, the engagement didn't last long as the couple split mid-October, which urged Grande to grace us with "thank u, next" mere minutes before SNL aired on November 3, 2018.

4. Malcolm, AKA Mac Miller

As we all know, the petite pop pioneer and Pittsburgh rapper go way back. Like, waaay back. In 2012, Grande had uploaded a festive duet of "Baby, It's Cold Outside" with Mac Miller on her YouTube channel. The next year, Grande's debut single, "The Way," also featured Miller and instantly became a hit and put her name on the map for super-stardom. The pair has also collaborated on a remix of Grande's Dangerous Woman hit "Into You" and Miller's "My Favorite Part" off his 2016 record The Divine Feminine.

The two have been there for each other in times of desperation, Miller comforted Grande shortly after the Manchester attack and Grande had continuously supported his sobriety on the road to recovery. Unfortunately, the pair broke up in May 2018 when Grande claimed their relationship was "toxic," and Mac Miller allegedly overdosed a few months later in September. Since then, Grande has paid tribute to her late ex-boyfriend, saying he "should be here" and that he is an "angel."