Big Sean's romantic history is one of the most talked-about in hip-hop. The Detroit rapper has been linked to four women — his high school sweetheart Ashley Marie, Glee actress Naya Rivera, pop star Ariana Grande, and singer Jhené Aiko — across a love life that spans two decades. His relationships have consistently intertwined with his art, from chart-topping collaborations to public breakups that fueled his music.
Who is Big Sean?
Sean Michael Leonard Anderson, born March 25, 1988, is an American rapper performing under the stage name Big Sean. He was born in Santa Monica, California, and later moved to Detroit, Michigan at two months of age. He met Kanye West as a teenager and signed with his record label GOOD Music in 2007. His albums Dark Sky Paradise (2015), I Decided (2017), and Detroit 2 (2020) all debuted atop the Billboard 200 and received Platinum certifications. He goes by @bigsean on Instagram, where he has 17 million followers.
Big Sean's Ex-Girlfriends: A Full Timeline
Big Sean's dating history includes his highly publicised relationships with singers Jhené Aiko and Ariana Grande, the late actress Naya Rivera, and his high school sweetheart Ashley Marie. He was engaged to Naya Rivera from October 2013 to April 2014. Big Sean and Jhené Aiko had been together close to a decade and share a child together.
Ashley Marie — The High School Sweetheart (2006)
Ashley Marie was Big Sean's girlfriend during his high school days in Detroit. Their relationship began in 2006, well before he reached massive fame. Big Sean's song Ashley is reportedly based on his relationship with her, according to BET. Sean said in an interview with BET that he still loves her and has no doubt she still loves him too. The relationship did not survive his rise to fame, but it clearly left a mark on his music.
Naya Rivera — The Cancelled Engagement (2013–2014)
The actress and the rapper made their relationship official in spring 2013 and announced their engagement in October of that same year. The couple met on Twitter. The engagement was one of the fastest in celebrity circles. The couple got engaged just six months after going public with their romance. In April 2014, Big Sean called off the engagement amid rumours that he had cheated on Rivera. A publicist for the rapper released a statement to Us Weekly: "After careful thought and much consideration, Sean has made the difficult decision to call the wedding off."
Rivera later shared her side in her memoir Sorry Not Sorry: Dreams, Mistakes and Growing Up, claiming that she learned of their split from the internet. The split turned acrimonious. Rivera claimed in the book that she found Ariana Grande at Big Sean's home not long before he called off their wedding. Big Sean's rep denied cheating allegations entirely, telling Us Weekly, "Sean did not cheat on Naya and the allegations are 100% false and untrue." Rivera tragically passed away in July 2020 after drowning in Lake Piru in California. Entertainment Tonight reported that Big Sean "liked" several tweets hoping for Rivera's safe return.
Ariana Grande — Eight Months and a Grammy Debut (2014–2015)
Sean and Grande first met in 2012 at a Wango Tango concert. News outlets reported that they were friends and longtime collaborators before their romance. In August 2014, the rapper and Grande were rumoured to be dating after paparazzi spotted them holding hands backstage at the 2014 MTV VMAs. Ariana started dating Big Sean in 2014 and they made their public debut at the 2015 Grammys. They dated for eight months, releasing their hit track Best Mistake. After eight months of dating, the two called it quits in April 2015. According to a source for E! News, the breakup was over conflicting schedules.
The overlap between the Rivera and Grande chapters was never far from the headlines. The breakdown of their relationship made headlines, with there being interactions between Jhené and Ariana whilst the pop star was still with Sean, most famously at the Grammys in 2015, just before the breakup. Grande later name-dropped Sean in her viral 2018 track thank u, next. He is one of the exes she mentioned, with the lyric: "Thought I'd end up with Sean / but he wasn't a match."
Jhené Aiko — Nearly a Decade, a Son, and a Split (2016–2025)
Big Sean began dating Jhené Aiko in 2016, years after the pair met at producer Ernest "No I.D." Wilson's studio. Jhené was featured on two songs from Sean's sophomore album Hall of Fame, and their relationship blossomed from there. The couple would later spark dating rumours after fans noticed their undeniable chemistry in music videos, even though she was married to producer Dot da Genius at the time. Aiko and Big Sean added more fuel to the rumours by sharing a kiss on stage in June 2016 following their performance at Power 105.1's Powerhouse festival.
Jhené and Sean first met in 2012, when the singer and rapper were both in different relationships, working solely as music collaborators. It wasn't until 2016, following the release of their joint album under the stage name Twenty88, that the couple confirmed they were dating. In August, Aiko filed for divorce from Dot da Genius, citing "irreconcilable differences." By this point, she and Sean had been photographed looking cosy together at numerous events.
Whilst they did have an on-and-off relationship dynamic, they seemed like each other's real love, always coming back together. Aiko confirmed in a comment shared on The Shade Room that she and Big Sean had split in early 2019. 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.
In 2022, the couple announced they were expecting their first child together on stage at Coachella. Two years after reconciling, Sean and Aiko welcomed their first child, a son named Noah Hasani.
Why Didn't Big Sean Marry Jhené Aiko?
This is the question fans have asked most. In an early 2024 interview, Big Sean claimed they hadn't got married because "there's a lot of work that needs to be done." In August 2024 on the Out of Context podcast, Sean was questioned if he and Jhené had secretly exchanged vows. The rapper dismissed it and added: "It's a little personal, you know what I mean? But just like to be real with you, just like any people who have dealt with love, we've had our ups and downs." The rapper continued by saying that marriage is the best part of any relationship.
The November 2025 Split
After more than ten years of love, music, and collaboration, Big Sean and Jhené Aiko reportedly called it quits in November 2025. When the split was first reported, it was alleged that the reason was because Aiko was upset with Big Sean for not moving towards marriage. The pair had supposedly been going through some issues over marriage, with Jhené offering up several ultimatums in the past. A source noted that Sean and Aiko are not having any dispute as a result of the breakup. "They both respect each other too much to let things get messy. They just want to do what's best for their child." Speculation about a possible split began after Jhené shared a song on Instagram featuring what many interpreted as subliminal lyrics about heartbreak and a breakup.
Sources allege that the split centred on marriage: "She wanted marriage — she wanted the commitment," one insider told AllHipHop. "Sean loves her deeply, but he just never wanted to take that final step." Aiko reportedly made "multiple ultimatums" before making her final decision.
Was Big Sean with Ariana or Jhené First?
Big Sean was engaged to Naya Rivera from October 2013 to April 2014, dated Ariana Grande from July 2014 to April 2015, and has been with Jhené Aiko since April 2016. So Ariana Grande came first, directly after the Rivera engagement ended.
Is Big Sean Currently Single?
As of 2026, reports suggest Big Sean and Jhené Aiko split for good as of November 2025, following an alleged disagreement over marriage after almost ten years together. Neither artist has issued a formal statement. Jhené Aiko has since stirred up dating rumours with rapper Larry June, after posting pictures to Instagram featuring the singer wearing a necklace with the rapper's iconic symbol, an orange.
Ultimately, Big Sean's romantic history has proven to be just as much of a focal point in the public eye as his chart-topping music career. From high-profile whirlwinds with Naya Rivera and Ariana Grande to a deeply collaborative, decade-long partnership with Jhené Aiko, his relationships have consistently intertwined with his art and personal growth. As he navigates this newly single chapter in 2026, it is clear that these profound personal connections—spanning two decades of love, heartbreak, and fatherhood—will continue to leave a lasting legacy on both his life and his music.
