The Women Who Defined Big Sean's Love Life: Inside The Breakups, Babies, And The Latest Jhené Aiko Drama

Few celebrity dating histories have been as public, passionate, and ultimately dramatic as that of rapper Big Sean. Sean Michael-Leonard Anderson, known professionally as Big Sean, has navigated a high-profile love life that has intertwined with some of the biggest names in music and television, leading to hit records, celebrated collaborations, and heart-wrenching public breakups.

As of December 2025, the conversation around Big Sean’s romantic status is once again dominating headlines, specifically concerning his long-term relationship with R&B star Jhené Aiko. With fresh, conflicting reports emerging about a recent separation, fans are looking back at the full timeline of the women who have shaped his life and career, from a whirlwind engagement to a global pop star relationship and a deeply meaningful, decade-long partnership.

The Defining Women: A Full Biography Profile

Big Sean’s romantic history is defined by three powerful, talented, and highly influential women, each of whom left an indelible mark on his life and public narrative.

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• Jhené Aiko (Ex-Partner & Collaborator)
  • Full Name: Jhené Aiko Efuru Chilombo
  • Born: March 16, 1988, Los Angeles, California, U.S.
  • Career Highlights: Grammy-nominated R&B singer-songwriter; known for albums like Chilombo and Souled Out; member of the duo Twenty88 with Big Sean.
  • Relationship with Sean: Began as friends and collaborators, transitioned to a romantic relationship in 2016. They share a son, Noah Hasani.
  • Current Status: Rumored to have recently separated in November 2025, though Big Sean has publicly denied rumors of a "new girlfriend."
• Ariana Grande (Ex-Girlfriend)
  • Full Name: Ariana Grande-Butera
  • Born: June 26, 1993, Boca Raton, Florida, U.S.
  • Career Highlights: Global pop superstar, Grammy winner, known for albums like Sweetener and Eternal Sunshine. Currently starring as Glinda in the upcoming film adaptation of Wicked.
  • Relationship with Sean: Dated for approximately eight months from 2014 to 2015.
  • Current Status: Continues to be one of the world's most successful artists, balancing her music career with major film roles.
• Naya Rivera (Ex-Fiancée)
  • Full Name: Naya Marie Rivera
  • Born: January 12, 1987, Valencia, California, U.S.
  • Died: July 8, 2020, Lake Piru, California, U.S. (Cause: Accidental Drowning)
  • Career Highlights: Actress and singer, best known for her groundbreaking role as Santana Lopez on the TV series Glee.
  • Relationship with Sean: Dated and was briefly engaged from late 2013 to early 2014.
  • Legacy: Tragically passed away in 2020 after reportedly exhausting herself saving her young son's life while boating on Lake Piru.

The High-Profile Whirlwind: Naya Rivera and Ariana Grande

Before his deep connection with Jhené Aiko, Big Sean had two of the most talked-about relationships in Hollywood, both of which ended abruptly and dramatically.

The Engagement That Ended on the Internet (Naya Rivera)

The relationship between Big Sean and Glee star Naya Rivera was a rapid-fire romance. They began dating in 2013 and were engaged just six months later, creating a media frenzy. The engagement was called off in April 2014, just a few months before he began dating Ariana Grande.

The breakup was famously acrimonious. Rivera later revealed in her memoir, Sorry Not Sorry, that she learned the engagement was off through the internet, not directly from Big Sean.

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The drama was further immortalized in music. Shortly after the split, Big Sean released the highly successful, yet controversial, track "I Don't F*** With You" (IDFWU). Though he has since stated he would not have written the song if he knew of the tragic events that would later occur, the track remains a permanent fixture in the narrative of their painful split.

Rivera’s life tragically ended in July 2020. Her death by accidental drowning while saving her son, Josey Hollis Dorsey, in Lake Piru, sent shockwaves through the entertainment industry, prompting an outpouring of grief and respect for her final heroic act.

The Pop Star Romance and the 'Thank U, Next' Mention (Ariana Grande)

Following his split from Rivera, Big Sean and pop sensation Ariana Grande confirmed their relationship in late 2014. The pair, who had collaborated on tracks like "Right There" and "Best Mistake," were a powerhouse couple for about eight months.

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Their split in April 2015 was attributed to conflicting tour schedules and, reportedly, Big Sean's raunchy lyrics about the pop star in his music.

Despite the breakup, the two maintained a level of mutual respect. Their relationship was immortalized in pop culture history when Grande famously name-dropped him, along with other exes, in her 2018 hit single "thank u, next." The lyrics "Thought I'd end up with Sean / But it wasn't a match" cemented their place as one of the most memorable pairings of the mid-2010s.

The Ultimate Partnership: Jhené Aiko and the 2025 Breakup Drama

The connection between Big Sean and Jhené Aiko is arguably the most significant and enduring relationship of his career. It transcended simple dating, evolving into a creative partnership, a co-parenting unit, and a long-term romance that lasted nearly a decade.

From Collaboration to Commitment: The Twenty88 Era

Big Sean and Jhené Aiko first worked together in 2012 and formed an immediate, undeniable creative chemistry. In 2016, they solidified their bond by forming the duo Twenty88 and releasing a self-titled concept album that explored the complexities of a relationship between two characters.

Their professional partnership soon became personal. They began dating in 2016, and the relationship was characterized by deep affection, public declarations of love, and a natural, seemingly unbreakable bond.

The Joy of Noah Hasani

The ultimate symbol of their commitment came on November 8, 2022, with the birth of their son, Noah Hasani. This milestone cemented their status as a family, even as their relationship faced the typical stresses of two demanding careers.

The Latest, Conflicting 2025 Updates

In a surprising and dramatic turn of events, reports surfaced in November 2025 suggesting that Jhené Aiko and Big Sean had ended their nearly ten-year relationship.

Sources close to the couple indicated that the primary reason for the split was a fundamental difference over commitment, specifically that Jhené Aiko desired marriage, while Big Sean was reportedly unwilling to take that "final step."

However, the narrative immediately became complex. Following the initial reports, and rumors that Big Sean had already moved on, the rapper took steps to publicly address the speculation. Big Sean vehemently denied claims that he had a "new girlfriend" and called out the negativity surrounding the breakup rumors, suggesting the situation was more nuanced than the media portrayed.

As of late 2025, while the status of their romantic relationship remains ambiguous amid reports of a separation, it is clear that their bond as co-parents to Noah Hasani remains paramount. The ongoing saga between Big Sean and Jhené Aiko is a testament to the challenge of maintaining a private, committed relationship under the intense scrutiny of the public eye, leaving fans to wonder if this is truly the end of the Twenty88 era or just a temporary pause.