Rapper Big Sean has had a handful of public relationships throughout his successful career in the music industry. The “Single Again” artist’s dating history includes off-and-on girlfriend Jhené Aiko, Ariana Grande, Naya Rivera and more.
Naya is commonly regarded as Sean’s most serious relationship, as the pair nearly got married in 2014 before deciding to call off their nuptials. According to the former Glee actress’ 2016 memoir, Sorry Not Sorry, she and Sean weren’t the best fit.
“I started to realize that I was dating an incredibly selfish person. I shook Sean awake and told him that Cory [Monteith] had just died. He just said, ‘Oh man, babe, I’m really sorry about that,’ and rolled over and went back to sleep,” Naya, who tragically died on July 8, 2020, penned at the time.
“I was crying and kept coming in and out of the room as I went out into the hallway to make phone calls, and he never got out of bed or even so much as sat up and turned on the light,” she continued. “This still blows my mind to this day.”
Naya also alleged that Sean began seeing Ariana Grande while they were still together. However, the “Imagine” singer didn’t officially start dating Sean until August 2014. The A-list duo dated for nearly a year before breaking up in April 2015. By all accounts, Ariana and Sean are still on good terms to this day.
In fact, the lyrics of her hit 2018 single “Thank U, Next” read: “Thought I’d end up with Sean/ But he wasn’t a match.” Additionally, in the music video, Ariana wrote “could still get it” in her mock Burn Book á la Mean Girls next to a picture of Sean.
Of course, that led to some mild dating speculation but the two seemingly never got back together. As for Sean’s dating life in 2020, he and ex-girlfriend Jhené Aiko appear to be back together after splitting in 2019 — at least it seemed that way in the spring.
In March, Sean gave the “Triggered” artist an incredibly heartfelt shout-out for her birthday. “Happy 3.16, Queen Jhene Aiko. Always proud but never surprised cause I know how great you are at everything you do,” he gushed. “Even though we gotta be inside [in] quarantine, you even make that sound good. I love you from [the] past life to the next.”
To learn more about Big Sean’s complete dating history, scroll through the gallery below.