While rapper Big Sean is known for his hit songs, he’s also well-known for his messy relationships. These drama-filled romances often make their way into his songs where the rapper doesn’t hold back.
Here’s the truth about Big Sean’s messy dating history.
Young Love
Sean Anderson was born in Santa Monica, California, and a few months after his birth, his family moved to Detroit, Michigan. At the age of 16, Sean Anderson met Ashley Marie. During an interview with Power 106, he explained that they didn’t start dating until two years later, and from that point on, he was head over heels. He said, “She was definitely my first love, she was somebody that supported me.”
As Sean started to experiment more with music, he started recording mixtapes and performing in Detroit. One person he could always count on to be in the crowd was his girlfriend Ashley. He told Power 106 that sometimes, she was one of the few people in the crowd and Sean called her one of his biggest supporters.
From Detroit to global success
In the summer of 2005, one of Sean’s friends called him and said Kanye West was at the local radio station and that he should go down to see if he could get signed. Sean told MTV he raced to the radio station and used his relationship with one of the staff members to get close to Kanye and asked if he could rap for him. Kanye initially denied him because he was in a rush and had to leave. Sean told him, “Man, please. You’re my hero. Let me rap for you? Just let me spit for you.”
Kanye softened up and allowed Sean to rap for him as he walked out of the radio station. Before they made it to the exit, they stopped in the doorway and Kanye turned to Sean and started bobbing his head.
Kanye was impressed, but he wasn’t signing any new artist to his G.O.O.D. Music label at the time. They lost contact until two years later in 2007 when Kanye brought Sean out on the road with him and finally signed him.
A startling allegation
He moved out to Los Angeles to kickstart his new career, and his first official mixtape entitled Finally Famous was released in June 2011. It debuted at number three on the Billboard chart, selling over 80,000 copies in the first week. He and Ashley were still going strong, and she even moved to Los Angeles to be with him. However, Sean was truthful about his codependency issues. He told Complex magazine, “I’ve always been the type that had a girlfriend. I’ve never really been single.”
In August 2011, Big Sean was on Wiz Khalifa’s Rolling Papers tour when he found himself in hot water. Sean and local Detroit rapper Willie Hansbro were accused of forcing themselves on a 17-year-old girl. According to MTV, the girl claimed the men touched her without her consent and unlawfully imprisoned her among other things. They were charged with several misdemeanors and released after posting $500 bail each.
According to Rolling Stone, the more serious charges were dropped in October, and he and Willie accepted a plea deal, which required him to simply plead guilty and pay a $750 fine.
It was a slap on the wrist, and the issue was behind him. Things began to crumble in his personal life though. In 2013, he told Necole Bitchie that Ashley didn’t enjoy living in Los Angeles and she wanted to move to New York. Sean pleaded for her to stay in L.A. with him, but she told him they could stay together and be in a long-distance relationship. Sean told the website, “For me, it was a little too hard.”
He told Power 106 they were too young to keep their relationship afloat, but he still had love for her. He said, “I made a lot of mistakes, she made a lot of mistakes, and, unfortunately, it didn’t work out.” After close to seven years together, it was over.
Finding love on Twitter
Before the dust could settle on his old relationship, Sean had already moved on with actress and singer Naya Rivera. Naya told Access Hollywood she followed him on Twitter, and he sent her a DM letting her know he was a fan. Naya said, “We went to dinner and the rest is history.”
They made their debut in April 2013 during a red carpet appearance. Not only did they look great together, but they also worked well together. Sean collaborated with Naya on the song, Sorry, where Naya took some shots at his exes. But Sean admitted to Billboard that he still had love for his ex-girlfriend Ashley Marie. In August 2013, he released his album Hall of Fame, which included a heartfelt tribute to his ex, entitled “Ashley,” which he wrote while they were still together. On the track, Sean admits to cheating on her. He told Billboard he played the song for Naya, and she loved it.
After about six months of dating, Big Sean proposed in October 2013, and Naya said yes. In December of that year, she told People magazine that planning for the wedding and their future was simple because Sean was eager to please her. Naya said, “He knows ‘happy wife, happy life!’ So, he’s kind of like, ‘Whatever you want, babe!’” She also said that Sean was very involved in the planning, and they were so in love and looking forward to becoming husband and wife.
A canceled wedding
But things didn’t work out. Sean’s rep released a statement to People magazine in April 2014, stating, “Sean has made the difficult decision to call the wedding off.”
How did things go so wrong? Well, sources claimed Sean had cheated with one of Naya’s castmates on the hit show Glee. Sean’s rep denied that accusation in a statement to People magazine.
Perhaps he wasn’t cheating with one of her co-stars, but Naya did find proof of another woman in the picture. She later disclosed in her memoir entitled Sorry Not Sorry that she and Sean were arguing for five days straight while he was traveling. When he returned to Los Angeles, he didn’t want to see her, but she had a key to his house so she let herself in. Naya wrote, “I walk in, go downstairs, and guess what little girl is sitting cross-legged on the couch listening to music? It rhymes with ‘Smariana Schmande.’” Naya also wrote that she learned their engagement was off from the internet and not from Sean himself.
Even though their relationship was over, the drama ensued. In a since-deleted tweet, Naya accused Sean of stealing her Rolex, while Sean’s sources told TMZ he simply took back a Rolex that he had loaned her.
Naya ended up marrying her longtime friend and actor Ryan Dorsey just three months after Sean ended their engagement. Sources state she tied the knot on the same day she and Sean were supposed to get married.
Sean & Ariana
Instead of taking some time to heal from back-to-back messy relationships, Sean didn’t stay single for long. He immediately jumped into a new romance with Ariana Grande, which pretty much confirmed Naya’s allegations that she caught Ariana in Sean’s house back when they were together.
A source told E! News that after working on Ariana’s song entitled “Problem,” they hit it off and became friends before entering into a full-blown relationship. In September 2014, Sean told US Magazine they had great chemistry, but he wouldn’t confirm if they were a couple or not. That same month, his single “IDFWU” was released, which many thought was aimed at Naya. He also rapped, “I got a new chick that I gotta thank God for.”
A month later, Ariana confirmed she and Sean were indeed a couple in an interview with The Telegraph. She added, “He is one of the most amazing men in the whole world.” Sean had strong feelings for her as well. In January 2015, he told Complex, “This is something special and I appreciate every moment of it.”
However, by April 2015, it appeared their romance was over. A source told TMZ Sean broke up with her because he thought she was immature. Sources also said Sean would make time to go see her and Ariana wasn’t reciprocating the effort.
There was a chance they would reconcile, but Sean reportedly ditched that plan after he believed Ariana set up a stunt where Justin Bieber jumped on stage while she was performing and grabbed her from behind. Sean believed Ariana orchestrated the whole act to hurt him, so he knew it was time to move on.
Moving on again
Of course, he didn’t stay on the market for long. In 2016, he teamed up with Jhené Aiko and released a joint album called Twenty88. Jhené told BBC Radio they had been friends for a while, but she was always in a relationship. She got married to producer Dot da Genius in 2016, but after 11 months of marriage, they divorced and she and Sean were finally able to step out as a couple.
Only a week after her divorce from Dot, Jhené got Sean’s face tattooed on her arm. In March 2018, there were allegations Sean was getting a little too cozy to singer Nicole Scherzinger at an Oscars’ afterparty. Shortly after the rumors emerged, Sean and Jhené took to social media and slammed the reports as “fan fiction”.
Behind the scenes, Sean was going through a lot. He ended up canceling a scheduled tour, and in June 2018, he told Billboard he was taking some time to nurture himself after battling depression and anxiety. He also got candid on his Instagram, where he revealed that after turning 30, he felt lost, and even his love for music wasn’t making him happy anymore. After speaking with a therapist and receiving spiritual guidance, he found out his life was lacking some clarity.
Sean and Jhené never officially confirmed their breakup, but in November 2018, Jhené covered up her Sean tattoo. By this time, Sean had removed everything involving the two of them from his social media, except for the cover of their joint album.
In November 2018, Ariana released a song called, “Thank U, Next,” where she sings, “thought I’d end up with Sean, but he wasn’t a match.” Despite the song, Sean was spotted in the studio with her in February 2019. A month later, Jhené officially confirmed they were over.
Since then, they’ve collaborated on more music together and they appear to be on-again-off-again. However, it looks more promising this time around. They appear to be back together and their relationship is stronger than ever.
There was a sad and unexpected turn in July 2020 after Naya suddenly passed away. In a touching Instagram statement, Sean wrote that he appreciated and cherished everything that happened between them. We send our condolences to Naya’s loved ones.
What’s next for Big Sean?
These days, Sean is making his mental health a priority. He told Ssense website he meditates every day and keeps a journal where he writes down affirmations.
After spending the bulk of his adult life in back-to-back relationships, he told the website he finally knows the difference between conditional and unconditional love. He also said he used to think material possessions were worth everything, but now he knows the truth. He said, “What’s worth everything is the emotion of real love from your family, from the people who will be there no matter what.”
Despite all he has gone through in his past relationships, we wish Sean the best on his journey to becoming the best version of himself.