Inside Big Sean And Jhene Aiko's Relationship

Sean Michael-Leonard Anderson, professionally known as Big Sean, and Jhené Aiko Efuru Chilombo both had star-studded dating histories before they found a love story in each other.

The "Triggered" singer dated singer O'Ryan Browner (brother of Omarion) between 2005 and 2008 and gave birth to their daughter Namiko Love. The R&B artist later confirmed she was married to producer Dot da Genius in March 2016, but was divorced by October 2017, according to Hot New Hip Hop. 

Prior to dating Aiko (the first time), Big Sean was publicly dating Ariana Grande and Naya Rivera. Rivera, who died in the summer of 2020 from drowning in a lake, was considered Sean's most serious relationship as he and Aiko were famously on-again-off-again between 2012 and 2019. 

However, the couple — jointly known as TWENTY88 — ultimately found their groove in late 2019 and have been going strong since. Keep scrolling to get the inside details of their union. 

According to Elite Daily, Big Sean and Jhené Aiko's relationship began as a friendship in 2012. Though Aiko expressed in a 2016 interview with Flaunt Magazine that she and the Detroit rapper did in fact go on a date, they were just friends. In a Billboard interview, the "Lightning and Thunder" singer considered it a positive since the two "were forced to really, really get to know each other on a friendship level." 

The friendship was ultimately a benefit as the two went on to release an album together in 2016 titled TWENTY88, their joint musical moniker. The project solidified their rumored romantic relationship, which was later confirmed by multiple social media shout-outs and even their own PDA.

Sometime in 2017, the mother of one got a portrait tattoo of the rapper's face, however the tat was covered up with a space- and dragon-themed piece the following year. The coverup sparked breakup rumors, which Us Weekly confirmed in December 2018. 

Their romantic timeline gets a little fuzzy around spring 2019. While the two were reportedly separated, Aiko clearly still had feelings for her ex and openly shared them. 

"You are so special. To me. To the world. While we're both still on this planet I just want to say... I love you beyond measure," she wrote in an Instagram comment, per Complex. "Even tho I get big mad and u trigger the f*** out of me. U make me feel. And I appreciate that."

Big Sean and Jhené Aiko's breakup may have seemed less than concrete because the two were still, well, friendly. Despite Aiko's vulnerable breakup single "Triggered," the singer was adamant that she wasn't hating on her ex. 

"I share about one percent of my whole being with the internet," she explained in a 2020 Essence interview. "Even in my songs, that's literally one moment that I'm talking about or when I felt that way. People hear a song like 'Triggered' and they're like, 'Oh, do we hate him now?' In the grand scheme of things that was like a moment." She later shared a photo of the two at the beach laughing seemingly to say "no hard feelings."

They also collaborated together again in November 2019 on Aiko's song "None of Your Concern," which sparked rekindling rumors, especially since the "Blessings" rapper bragged about making the California native climax nine times in one day. Um, okay big Sean.

It wasn't long before Jhené Aiko and Big Sean were back to popping up on each other's social media profiles. In December 2019, they attended Diddy's 50th birthday party together and weeks later brought in 2020 at Jay-Z and Beyonce's New Year's Eve party, per Hollywood Life. 

It was pretty obvious they were back on the up and up again and solidified their cuteness with a Valentine's Day trip to Disneyland. Who doesn't love matching outfits? And while they didn't confirm their relationship, the pet names were on full display by March when Big Sean promoted Aiko's album Chilombo on his Instagram, writing, "congrats baby, you earned this one."

In April 2020, the rapper crashed Aiko's Instagram Live with fans and handled the marriage question like a champ. Aiko probed, "Why don't you marry me?" To which Big Sean replied, "It's in the works. Don't even trip."

Then there's the subtle hint in the music video for their collaboration "Body Language" off of Big Sean's album Detroit 2. In the video, they portray couples from '90s Black films including Poetic Justice and Love Jones. In the final movie portrayal, The Best Man, Big Sean is at a bachelor party. Could this be another sign of a potential real-life final hoorah? Only time will tell, but as of late 2020, it looks promising.