Sean Michael Leonard Anderson, known globally as Big Sean, has navigated a high-profile career in music alongside a series of significant romantic relationships that have often garnered public attention. His journey through love has seen him move from long-term high school romance to highly publicized engagements and, ultimately, to a profound partnership that has shaped both his personal life and his artistry.
Big Sean's earliest known public relationship was with his high school sweetheart, Ashley Marie. The couple began dating in early 2006 and maintained their relationship for nearly seven years, a significant period that spanned his early career ascent. Reports indicate that the challenges of a long-distance relationship, with Ashley in New York and Sean in Los Angeles, contributed to their eventual split in early 2013. Sean later penned the song "Ashley," reflecting on their time together.
Following his long-term relationship, Big Sean began dating actress Naya Rivera in April 2013. They initially connected on Twitter, with Rivera following him and Sean sending her a message, leading to their first dinner date. Their romance quickly escalated, and they announced their engagement in October 2013.
However, their engagement was short-lived, with the couple calling it off in April 2014. The breakup was notably public and at times contentious, with Rivera later alleging in her memoir that Sean had cheated on her. Despite the difficult end, Big Sean paid a heartfelt tribute to Rivera following her tragic passing in 2020, acknowledging their shared history.
Soon after his split from Naya Rivera, Big Sean's relationship with singer Ariana Grande became public in October 2014. The two had been friends and musical collaborators for some time, working on tracks like "Right There." Their romance was highly visible, with the couple frequently seen together at events and in public, often holding hands.
Their relationship lasted for approximately eight months, concluding in April 2015. Despite the breakup, both artists have maintained that they remained on friendly terms. Their collaboration and public appearances marked a notable period in both of their careers.
Big Sean's most enduring and significant relationship has been with singer Jhené Aiko. Their connection began as a professional one, with Aiko featuring on Sean's songs as early as 2012, including "Beware" and "I Know." While Jhené was in another relationship when they first met, their undeniable chemistry led to speculation.
In 2016, their musical partnership evolved into the collaborative duo Twenty88, releasing a joint album that further fueled rumors of a romance. It became evident that their relationship extended beyond music, and they publicly confirmed their romantic involvement around this time. Their dynamic has been described as an on-again, off-again journey, marked by deep affection and mutual support.
The couple has often spoken about their profound connection, with Jhené Aiko revealing that she saw qualities in Sean that reminded her of her late brother. In 2020, Big Sean shared in his song "Deep Reverence" that Aiko had experienced a miscarriage, a testament to the personal depth of their bond. Their relationship has been a source of inspiration for both artists' work.
In 2022, Big Sean and Jhené Aiko welcomed their son, Noah Hasani, into the world, marking a new chapter in their lives. Despite their long-standing relationship and the birth of their child, they have not yet tied the knot. Big Sean addressed the topic in a recent interview, stating that while he desires marriage, there's "a lot of work that needs to be done" within their relationship, acknowledging the ups and downs they've navigated.
"To me, marriage symbolizes like the best relationship," Big Sean stated, emphasizing the personal growth and navigation required.
Their journey continues to be one of the most closely watched in the music industry, characterized by their deep personal connection, shared artistry, and evolving family life. Big Sean's romantic history reflects a progression from youthful love to mature partnerships, culminating in a profound bond with Jhené Aiko that has become a cornerstone of his life.