Timeline of Big Sean’s Relationship with Girlfriend Jhene Aiko

Big Sean and Jhené Aiko have been an on-and-off couple for a long time. Their relationship may have started in 2016, but they have known each other for longer. Let’s take a closer look inside their relationship.

Big Sean, named Creative Director of Innovation for the Detroit Pistons in 2021, was born Sean Michael Leonard Anderson on March 25, 1988. The rapper began his music career in 2007 but gained popularity in 2010 before the release of his 2011 debut studio album “Finally Famous.”

Jhené Aiko Efuru Chilombo is a singer and composer born on March 16, 1988. The mother of one who started her career in 2002 is also known for her short film “Trip.”

Big Sean and his girlfriend Jhene Aiko at the NAMI West LA Moroccan Gala Honoring Jhene Aiko on May 20, 2018 | Source: Getty Images

MAY 2012

In an interview, Aiko revealed that she and Sean became friends in 2012 after her brother passed away. Aiko’s brother was diagnosed with an inoperable brain tumor in 2010 and died at 26 in 2012.

She had just met him, and they worked on “Beware” with Lil Wayne and “I’m Gonna Be.” Aiko said Sean wanted to take her out on a date. She had a boyfriend but informed him before going on a date with Sean as a friend.

The date was also the first time she was courtside at a basketball game, and she said Sean was incredible. However, her relationship with her then-boyfriend fizzled after discovering he was secretly married to his baby mother.

By the time Aiko was ready to give Sean a chance, he was already in another relationship, but they remained friends. Eventually, they became closer than friends.

2016

2016 was the year Aiko and Sean became closer. In March, they formed a new music group, TWENTY88, and on April 1, 2016, they released a joint album, “Twenty88.” Def Jam, in their press release, described the album as:

“The story of the highs and lows of a relationship, with insights into conflict, memories, love, sex, and more.”

Aiko and Sean did not confirm their relationship status when their album was released. However, she had been separated from her producer husband, Dot Da Genius, whom she married on July 26, 2014.

Despite not confirming their relationship status, they were already obsessed with each other and supported each other when they had to perform at shows. In an interview, Sean said:

“Jhené is more than just a friend. I don’t know how else to describe it — me and her are just cool like that. I love her and I know she loves me. I was down to make that commitment — something that will last and be different from the rest.”

Even though Aiko separated from her husband in June 2015, she only filed for divorce in August 2016, and this further fueled the speculations and rumors that she did it because of Sean.

OCTOBER 2017

Aiko’s divorce was finalized on October 3, 2017, and less than a week later, a photo of her with a new tattoo of Sean surfaced on the internet. However, there was no detail as to when she got the tattoo.

In the picture, Aiko waved to a crowd during a performance when fans spotted the tattoo. The tattoo showed Sean wearing a bowtie and tuxedo, and it was done by celebrity artist Miryam “The Witchdoctor” Lumpini.

NOVEMBER 2018

While their relationship took a steamy turn in February 2018 with suggestive Instagram comments by Aiko, by November 2018, there seemed to have been trouble in paradise.

Aiko returned to Lumpini to cover Sean’s face on her arm. Lumpini shared Aiko’s new tattoo, a swirling galaxy with a rocketship and twinkling stars. Her actions instantly triggered speculations that they had gone their separate ways.

MARCH 2019

By March 2019, Aiko and Sean had called it quits. Soon after, there were rumors that he hung out with his ex-girlfriend Ariana Grande. A source revealed that Aiko and Sean split in mid-December 2018. The source said:

“I wouldn’t say it was amicable. But now they are civil towards each other.”

Sean was reportedly seen with Grande when leaving a recording studio in his car. The duo, who dated for eight months and broke up in October 2015, had spent hours at the studio.

MAY 2019

In early May 2019, Aiko released an emotional ballad titled “Triggered,” it was apparent what the song was about. The song was a freestyle full of emotions and focused on the familiar feelings one feels after a breakup.

Despite fans thinking that she threw shots at Sean, Aiko revealed that she usually shares about one percent of her whole being with the internet. Even when she sings, she’s generally focusing on one moment and how she felt in that moment.

However, she revealed that when Sean heard the song, he was stunned. He told her he was not her friend, and she told him it was just a song and how she felt at that moment, and it was not 100 percent about him.

NOVEMBER 2019

In November 2019, Aiko released a new song, “None of Your Concern,” and her fans were shocked because she featured Sean. The introspective music touched on their relationship, and in his verse, Sean revealed that he doesn’t think any average Joe deserves her.

Shortly after their collaboration, fans spotted them hanging out together when they grabbed dinner at a fancy restaurant sparking rumors of their reconciliations.

JANUARY 2020

By January 2020, Aiko and Sean had not confirmed if they were back together, and they continually kept their fans guessing. Aiko fueled the speculations further when she posted a picture of them together on New Year’s Day.

Aiko, who wore a festive “Happy New Year” headband, shared a picture of them cozied up in a selfie and making funny faces at the camera as they welcomed the new year together.

SPRING 2020

In March 2020, when Aiko celebrated her birthday, Sean took to his Instagram to post several pictures of them, including a sweet throwback photo, and wish her a happy birthday. In the caption where he called himself lucky, he said:

“Happy 3.16 Queen @jheneaiko! Always proud but never surprised cause I know how great you are at everything you do. Even tho we gotta be inside n quarantine, you even make that sound good. I Love you from da past life to the next . 32 the Magic year.”

During a live Instagram session during the quarantine, Sean told Aiko that she looked good, and she jokingly replied, “why don’t you marry me?” Without mincing words, Sean replied, “it’s in the works. Don’t even trip.”

AUGUST 2020

In August 2020, Sean released a single titled “Deep Reverence” featuring the late Nipsey Hussle. In his verse, Sean said:

“What’s coming is going if it don’t give you more, it drains you. Should be a billionaire based on the time off I’m not taking. Probably why this […] with me get crazy and we lost a baby.”

Even though Sean did not mention names, the line about losing a child through a miscarriage had fans speculating that he was expecting a child with Aiko. However, she never responded to the rumors.

JULY 2022

While the couple never addressed the topic of the miscarriage, in July 2022, Sean and the Chilombo singer were spotted walking in Beverly Hills, and she had a baby bump. Aiko representative said:

“The couple is overjoyed and looks forward to this next chapter.”

Rumors that they were expecting their first child together began in June after a fan took to social media to reveal that he saw the couple at a Whole Foods store and Aiko was pregnant.

While the couple has not officially announced their pregnancy, Sean wished his mother and Aiko a Happy Mother’s Day in May 2022. On July 3, 2022, Aiko posted a throwback picture of herself as a child, but she was holding her stomach, hinting at being pregnant.

Fans took to Aiko’s comments section to congratulate her. While this would be Sean’s first child, Aiko welcomed her first child, Namiko Browner, with her ex-boyfriend actor O’Ryan Omir Browner on November 19, 2008.

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