Ariana Grande's well-publicized relationships have been frequent, fiery, and fleeting—plus, they're now immortalized in one of the most epic pop breakup songs of all time, the 2018 anthem "Thank U, Next." With the release of that track, not to mention a song literally named after one of her exes in 2019, Grande has placed herself within a small crew of specialists that includes Taylor Swift and Adele.
But no matter how impressive Ariana Grande's rebounds might seem, as she dives headlong into another relationship hot on the heels of the last or drops another diss track celebrating her independence, the fact remains that she's a confirmed serial monogamist with an impressive string of boys in her past.
It's hard not to imagine that wherever she goes, Ariana isn't on the hunt for her next fling. Keep scrolling for 15 pics of Ariana Grande with her exes, plus 5 when she's clearly single and hunting.
20 Mac Miller
Perhaps Ariana Grande's most publicized relationship was with the late Mac Miller. Following their breakup, Miller's decline was sad and shockingly swift, something many fans attributed to his split from Grande. But while they were together, the two were funny, quirky, and definitely cute, often posing for photos to show off their feelings.
19 All Dressed Up
Mac Miller's rap career began in his hometown of Pittsburgh, though both he and Arian Grande ended up becoming jet-setters enjoying the music life across the entire globe. Even when they dressed up to the nines, though, both let their unique attitudes shine through. Only Ariana knows what really went down between the two that led to their breakup.
18 Nathan Sykes
Ariana Grande's relationships are sometimes quick and painless, which seems to be the case with former British boy-band member Nathan Sykes. As reported by Seventeen, the two spotted each other on the red carpet and ended up performing a duet for the film Mortal Instruments: City of Bones. But Sykes wouldn't last long.
17 The Forgotten Man?
Ariana Grande has become akin to Taylor Swift and Adele, two other pop singers who air their dirty laundry out in breakup songs. But many Ariana fans have noticed that Nathan Sykes was conspicuously absent from his ex-girlfriend and singer-songwriter's 2018 smash "Thank U, Next" and have concluded that maybe she holds less of a grudge about this guy.
16 Single And Looking: Over Here, Over There
For serial monogamists like Ariana Grande, the moments without a serious significant other can seem eternal. But on the other hand, for famous starlets like Ariana Grande, those moments of loneliness can easily be brought to an end—the only problem is the immense publicity and paparazzi attention that she draws whenever she's spotted with a guy of the right age.
15 Graham Phillips
Graham Phillips is one of Ariana Grande's less-publicized boyfriends, known mainly for his roles on Riverdale and in Evan Almighty. Maybe their relationship was more of a career move for the child actor trying to make his way into the big leagues—it happens in Hollywood—though the two managed to stay out of the tabloids more than some other pairings.
14 Changes Ahead
It seems like every Hollywood star these days has a few websites dedicated to their transformations over the years. Here, Ariana's former looks are on full display in an early pic with ex Graham Phillips. The two dated from 2008 to 2011, so maybe Grande would say she has matured naturally since then.
13 Single And Looking: Okay, Go
In this shot, Grande looks like she's just spotted someone from across the room and everyone knows that when she sees it and she likes it, she wants it and she's gotta have it. From the way she described her first glimpses of Pete Davidson and Nathan Sykes, she seems like the kind of person who does just that.
12 Ricky Alvarez
Ariana Grande clearly isn't above fraternizing with the help, as evidenced by her relationship with her backup dancer, Ricky Alvarez. TMZ caught the two kissing in a donut shop, which came after fan speculation had already begun circulating after a well-publicized kiss during a live performance at the 2015 New York LGBT Pride festival in 2015.
In 2018, paparazzi discovered that Ariana and Ricky Alvarez were hanging out again, though apparently they are just friends now. Most fans of the pop singer apparently believe that the two broke up in July 2016, when Ariana posted and liked a few suspicious comments on various social media accounts.
10 Jai Brooks
The strict definitions of celebrity have changed in the last decade, which makes it seem more reasonable that a pop star like Ariana Grande might be willing to get hooked up with a prank video star from Australia. According to Ariana Grande's Fandom Wiki, she met Jai Brooks strictly online before an in-person introduction in 2012.
9 Single And Looking: Hang Up Right Now
This candid photo looks like a photographer snapped a pic at the very moment that a bad decision was hatching. From the oversized sweatshirt to the coffee cup on the ground, this looks more like the kind of call a sorority sister might make at the end of a long night than something a pop princess might have to do to get the guy she wants.
8 Accusations And Reconnections
Boys seem to flit in and out of Ariana Grande's life at warp speed, something that might make it seem likely she's a serial monogamist who might find the new thing before the old thing is over. Jai Brooks accused her of cheating on him with Nathan Sykes in 2013, though fans would probably believe Ariana's word over that of a professional prankster.
7 Big Sean
Probably the biggest name in Ariana's crowded closet is Big Sean. The rapper had featured on a few of her songs and she often quoted his work during interviews of her own. After plenty of speculation swirled for years, before Grande admitted they were dating to The Telegraph in 2014.
6 On Again Off Again?
In more recent times, Grande and Big Sean have been spotted together again, though both apparently say they aren't back together. It would be surprising if the duo got back together, though not entirely unheard of, especially after Us Weekly reported that they only broke up because of scheduling conflicts and remained close.
5 Single And Looking: Thigh Highs
This recent shot of Ariana Grande is recognizable as being from the "Thank U, Next" era thanks to the increased size of her upper lip. The question is whether releasing a string of breakup songs will dissuade any potential suitors from getting involved with the kind of girl who might air her dirty laundry happily for the whole world to see and hear.
4 Jordan Viscomi
Dancing clearly brings performers closer together and given the provocative nature of Ariana Grande's live shows, it's no surprise that she's developed some chemistry with her backup dancers. Just imagine all those long rehearsals, which clearly led to Grande developing feelings for short-lived boyfriend Jordan Viscomi, which she revealed in a Just Jared Jr interview.
3 Pete Davidson
Ariana's relationship with Mac Miller was barely over before speculation began to grow that she'd developed a new fling with comedian and SNL cast member Pete Davidson. The two were later engaged, before breaking up by October 2018. Davidson is well-known as part of the "Thank U, Next" diss track and even has his own song named after him now.
2 Real-Life Struggles
As much as Ariana Grande may have tried to play cool and suave after her breakup from Pete Davidson, he seems to have handled things slightly better. It's hard to believe that she's not upset after the breakup songs, while he has gone on to date Kate Beckinsale and Kaia Gerber. Ariana's famous lollipop photo seems to suggest the nature of his attraction with women that most men can only dream of.
1 Single And Looking: Those Boots, Though
No matter how happy Ariana might want everyone to think she is without a boy-toy to tote around, most people just aren't buying it. Sure, she's a strong-willed woman who has earned her financial—not just spiritual—independence, but everyone knows what boots that go up over the knee mean, especially when they're high-heeled.
Sources: Just Jared Jr, The Telegraph, Us Weekly, and Ariana Grande Fandom.