Sean Michael Leonard Anderson, known by his stage name Big Sean, has caught fans’ attention for various reasons, including his music career and messy love life.

Big Sean began his music career in 2007 after signing to Kanye West Good Music and Def Jam Recordings label. Big Sean became a household name in 2010 following the release of his debut studio album “Finally Famous.”

Big Sean’s dating history consists of his high-publicized relationships with singers Jhené Aiko, and Ariana Grande, the late actress Naya Rivera, and his high school sweetheart Ashley Marie.

Who is Big Sean Dating Now?

Big Sean is currently dating his longtime girlfriend, Jhené Aiko. The pair, who have musically collaborated in the past, have had an on-and-off relationship since 2016. Sean and Jhené Aiko recently welcomed their first child together in November 2022.

Aiko and the Detroit rapper revealed the news by sharing similar pictures and touching captions on their social media page.

Big Sean’s Dating Timeline

Although Sean has currently settled down, his past relationships have led to very public dramas. He’s repeatedly been accused of cheating or allegedly being involved with someone in a relationship.

Take a stroll down memory lane of Sean’s dating history, which involves his current girlfriend, Jhene Aiko, and exes Ariana Grande, Naya Rivera, and Ashley Marie.

Jhené Aiko and Big Sean. (Photo: @jheneaiko/Instagram)

Big Sean and Jhené Aiko (2016-Present)

Big Sean began dating Jhené Aiko in 2016, years after the pair met at producer Ernest “No I.D.” Wilson’s studio.

Sean and Aiko’s first encounter occurred in 2012 when they collaborated on the rapper’s “Beware” and “I’m Gonna Be” tracks. “Beware” was featured on his “Hall of Fame” studio album, which was released in August 2013. The song “I’m Gonna Be” was on the rapper’s 2013 album “Good Music Chicago.”

In 2016, Aiko told Flaunt magazine that shortly after meeting Big Sean and getting to know each other, they went on a date even though the singer was romantically involved with another guy.

She said, “We went on a date. We went to a Lakers game. It was a long time ago […] first of all, I had a boyfriend and me and Sean had already met. We were friends. So he asked me to go out with him, and even though I had a boyfriend.”

Although it is unclear if anything happened between Big Sean and Aiko, the pair continued to collaborate on more music. In 2015, Aiko and Big Sean starred in the rapper’s “I Know” video off of his “Dark Sky Paradise” album. The following year, Big Sean and Aiko released their joint album “Twenty 88.”

The couple would later spark dating rumors after fans noticed Big Sean and Aiko’s undeniable chemistry in their music videos, even though she was married to producer Dot da Genius at the time. Aiko and Big Sean added more fuel to the rumors by sharing a kiss on stage in June 2016 following their performance at Power 105.1’s Powerhouse festival. 

Aiko and Dot da Genius married in 2014 but split in August 2016 after the singer filed for divorce. Aiko’s divorce was finalized in October of that same year. Following Aiko’s divorce, the singer and Big Sean would go on public outings and display their love on social media or in interviews. 

All appeared to be going well with the couple until early 2019, when fans noticed Big Sean and Aiko were silent about their once-public relationship. Aiko confirmed in a comment shared on The Shade Room that she and Big Sean had split. There was no reason presented for the breakup at the time. 

The split appeared to have been short-lived, because the pair would ultimately be back together in early 2020. Two years after reconciling, Sean and Aiko would welcome their first child, a son named Noah Hasani.

Screenshot of Ariana Grande’s ‘Right There’ featuring Big Sean.

Big Sean and Ariana Grande (2014-2015)

Sean dated American singer Ariana Grande in 2014. News outlets reported that Sean and Grande were friends and longtime collaborators before their romance. 

The pair first met in 2012 at a Wango Tango concert. Sean and Grande would keep in contact over the years and record songs together. The rapper first appeared in Grande’s “Right There” single off of her debut album “Yours Truly.”

The pair’s relationship would blossom in 2014 after Sean and Grande recorded songs “Best Mistake” and “Problem” for the singer’s “My Everything” album. The Boca Raton native and Sean would ignite dating rumors after they were spotted backstage holding hands at the VMAs in August 2014. 

A month later, the couple was caught kissing at iHeart Radio Music Festival and other locations. Despite the evidence, Sean and Grande wouldn’t publicly confirm their relationship until October 2014. Grande would finally spill the beans during an interview with The Telegraph. 

Sean and Grande ultimately made their red carpet debut as a couple at The Grammy Awards in February 2015. After that, Big Sean and Grande would parade their love whenever they could on social media and in press junkets. 

Months following their red carpet debut, Grande and Sean would go their separate ways in April of that same year. At the time, TMZ reported that Sean and Grande’s breakup stemmed from the singer’s immaturity and unwillingness to make time for him. 

Their relationship lasted nine months. Despite breaking up in 2015, Sean and Grande would temporarily reunite years later in 2019 following his split from Jhené Aiko. 

Big Sean and Naya Rivera. Photo:@nayarivera/Instagram

Big Sean and Naya Rivera (2013- 2014)

Naya Rivera dated rapper Sean in 2013 after the pair met and exchanged messages on Twitter. Following their social media interaction, Sean and Rivera would ultimately meet and go out to dinner. A short time later, the stars became an item. 

Big Sean and Rivera would make their red carpet debut in April 2013 after attending the premiere of Jackie Robinson’s biopic “42,” starring Chadwick Boseman, at the TCL Chinese Theater in Hollywood, California.

The television personality and Sean took their relationship a step further by collaborating on Rivera’s single “Sorry,” which was released in September 2013. One month later, it was announced that the couple was engaged after Rivera was spotted rocking a diamond ring at Latina magazine’s Hollywood Hot List Party. 

All appeared to be going well for Sean and Rivera until April 2014, when the rapper revealed on Twitter that the engagement was over. After sharing the news, rumors began circulating online that Big Sean may have cheated on Rivera. At the same time, TMZ reported that Big Sean called it quits because of Rivera’s allegedly violent and controlling behavior. 

Soon after their breakup, Rivera got into a relationship with her longtime friend and actor Ryan Dorsey. Rivera and Dorsey got married in July 2014. The couple would welcome their only child, a son named Josey Dorsey, in 2015. Rivera and Dorsey would ultimately split in 2018. 

As for Sean, following his breakup with Rivera, the rapper would go on to date Grande. Rivera accused him in her 2014 memoir “Sorry Not Sorry: Dreams, Mistakes, and Growing” of cheating on her with Rivera. 

On July 8, 2020, Rivera would pass away after she drowned while boating with her son Josey. Big Sean would pay tribute to her and send his condolences to her family and fans in a heartfelt Instagram post. 

Big Sean and Ashley Marie (2006-2013)

Sean met his high school sweetheart Ashley Marie in 2004 when the rapper was 16 years old at Cass Technical High School, but the pair wouldn’t date until two years later in 2006. The Detroit native recalled during an interview with Power 106 Ashley Marie as his first love and opened up about the endless support she gave him when he first started out in the music industry.

Although limited details are known about Big Sean and Ashley Marie’s relationship, it was revealed that the couple split in early 2013 after the rapper was spotted hanging out with the “Glee” star Rivera in March of that same year.

In April 2013, Sean shared with DC’s radio station 93.9 WKYS that his relationship with Ashley Marie ended because the pair grew apart during their long-distance relationship.

He said, “I’ve always kinda been in a relationship, since I was 18 or 19 when I got with her, and things didn’t work out, not because of this music stuff. Sometimes when you’re with somebody, and you’re 18, you grow up. And it was long distance. She lived in NY, I lived in L.A. — you grow apart as people. Nothing more or nothing less, it wasn’t like I changed. We just really had our differences.”