A Look Back at Ariana Grande’s Dating History

When it comes to love, Ariana Grande has experienced her fair share of ups and downs.

From falling head over heels to having relationships only last a few short months, Grande is no stranger to having loved and lost.

Ariana Grande
Ariana Grande | Photo by Kevin Mazur/Getty Images for AG

Grande’s teenaged romances

Though Ariana Grande has had her fair share of romances throughout the years, the singer’s first known relationship wasn’t too long ago.

Back in 2008, the singer dated actor Graham Phillips.

Ariana Grande and Graham Phillips
Graham Phillips and Ariana Grande| Graham Phillips via Instagram

The pair met while they were both starring on Broadway in 13: The Musical and went a few years maintaining a pretty solid relationship.

However, in 2011, Grande and Phillips decided to go their separate ways due to their hectic schedules and no longer having the time to spend with one another.

Despite having ended their relationship, the former couple has remained close friends throughout the years and continue to maintain their friendship to this day.

One year after calling it quits from Graham Phillips, Grande began dating The Janoskians star, Jai Brooks.

Ariana Grande and Jai Brooks
Jai Brooks and Ariana Grande| Jai Brooks via Instagram

While the couple dating for a little more than a year, they eventually broke up in October 2013 after Brooks took to Twitter to accuse Grande of cheating on him with The Wanted’s Nathan Sykes.

“Yes I was cheated on. Yes it does suck,” he wrote in a lengthy rant. “Yes I was left for another man.”

Though Grande and Brooks got back together the following year, they broke up for good in August 2014.

The singer’s romance with Big Sean

One of Ariana Grande’s most notable romances was her eight-month relationship with rapper, Big Sean.

The two started dating in October 2014 following months of consistent speculation.

Grande confirmed their relationship that same month by admitting during her interview with The Telegraph that Big Sean was, in fact, her boyfriend.

 “He is one of the most amazing men in the whole world, and that includes my grandfather and my brother,” she said. “I think the world of him, and he’s an amazing person. That’s kind of all there is to it.”

Big Sean and Ariana Grande
Ariana Grande and Big Sean |Photo by Jason Merritt/Getty Images

While it still remains unclear how Ariana Grande and Big Sean came to be a couple, the rapper’s ex-fiancée, Naya Rivera, alleged in her book, Sorry Not Sorry, that she found the singer at his home while she and Big Sean were still in a relationship, which ended in April 2014.

Though things between Ariana Grande and Big Sean were going strong in the beginning, the couple eventually ended their romance after only a few months.

Her undeniable connection with Mac Miller

Although Ariana Grande most likely experienced love with all of her past boyfriends, her relationship with Mac Miller was on a completely different level.

The “Breathin” singer and “Self Care” rapper first met in 2013 after collaborating on Grande’s song “The Way.”

The couple started out as being friends and officially began dating three years later.

Throughout their two year relationship, fans could see that Grande and Miller were the happiest when they were together.

From always laughing when they were with each other to constantly showcasing their love on social media, fans were certain this relationship was going to last for years to come.

Ariana Grande and Mac Miller
Ariana Grande and Mac Miller| Ariana Grande via Instagram

Though Ariana Grande was hopelessly in love with Mac Miller, the singer broke off their relationship in May 2018 due to his constant drug use.

Despite their split, Grande and Miller continued to support and love each other leading up to the rapper’s unexpected death in Septemeber 2018.

Since his death, Grande has continued to honor Mac Miller’s memory in many different ways, one of which included her paying tribute to him in her song, “Thank U, Next,” singing, “Wish I could say, ‘Thank You’ to Malcom / ‘Cause he was an angel.” 

A short-lived engagement to Pete Davidson

Shortly after her relationship with Mac Miller ended, Ariana Grande began dating Saturday Night Live comedian Pete Davidson.

The pair first met in 2016 when Grande was the host and musical guest at SNL.

Two years later, Davidson confirmed their relationship by sharing a photo of him and Grande posing in Harry Potter outfits on Instagram.

After a month of dating, it was revealed that comedian and Grande had gotten engaged, with Pete Davidson proposing with a $93,000 diamond ring.

Throughout summer 2018, the couple constantly flaunted their romance as they were always spotted walking hand-in-hand and never being afraid to pack on the PDA.

Pete Davidson and Ariana Grande| Photo by Nicholas Hunt/Getty Images for MTV

The couple eventually moved into a lavish NYC condo together and even adopted a pet pig.

Though things were going well for the couple, their relationship shockingly came to an end a few short weeks after Mac Miller’s death.

Who is Ariana Grande dating now?

A few months after taking a much-needed break from dating and relationships, Ariana Grande is now giving love another try.

The singer is currently dating Social House member, Mikey Foster, who recently collaborated with Grande on her hit song, “Boyfriend”.

While the couple was rumored to be dating shortly after the release of their collaboration, it wasn’t until recently that their relationship was confirmed.