Jean Elie, ‘Insecure’ alum and star of upcoming ‘Send Help’ is engaged!

'Insecure’s Jean Elie is engaged to longtime love Randal Bailey and ready to plan a traditional Haitian wedding with loved ones and local cuisine. 

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Insecure alum Jean Elie, who played “Ahmal Dee,” younger brother of lead character Issa, has found his person—and is now happily engaged to her! Elie’s girlfriend, Randal Bailey, said “yes” when the actor popped the question last month during their vacation in Greece. 

Jean Elie, right, and fiancée Randal Bailey
Photo: Sara Popovic

During an interview with Essence, the Haitian-American actor shared that it was tricky to find the perfect time and setting to propose. He said, “I was sweating bullets all day because I knew I wanted to propose on our way to Mykonos,” but he ruled out doing it [right] “out the shower,” or “at dinner” because those also felt like “corny” options.

However, when fireworks went off unexpectedly beside the ocean while the couple enjoyed drinks, Elie knew it was the right moment to ask for Bailey’s hand in marriage. He described it as “beautiful,” deciding, “it can’t be anything better than this.” So, he went for it.

Elie recounted the proposal, “I said, ‘There’s a lot of things I want in life, and right now the only thing I want is you. Will you marry me? She said yes, and then she was like, ‘This is f-king really happening’ I said, ‘Yes. the f-k it is.’”

Jean Elie and Randal Bailey theGrio.com
Photo: Sara Popovic

With that said, Elie and Bailey have different wedding philosophies for the big day. For Bailey, a large wedding with any “pomp and circumstance” is unnecessary; she would be fine simply going to the courthouse if it meant being married to the love of her life. Elie, on the other hand, is set on a sizable ceremony with loved ones and many Haitian traditions. His long list, of course, also includes plenty of his favorite Haitian foods.

“We’re going to have some griot, lambi, tassot. We’re going to have the whole gamut of Haitian food” he said. “We’re going to have Haitian music playing.” Fortunately, the two have already learned the importance of compromise in their relationship. For instance, Elie knows Bailey “doesn’t like to dance much,” but she’s been willing to practice some Compas (modern merengue dance music of Haiti). This is ideal preparation, as Elie’s family enjoys partying, meaning the atmosphere will be festive on the big day. 

Much like an episode of the much-beloved Insecure, Elie and Bailey’s relationship began as lowkey complicated, as they first crossed paths during a bonfire at Dockweiler Beach in Los Angeles. Bailey was getting over a “rough breakup,” but decided to join her cousin for the gathering that day. While venting to her cousin about the upsetting breakup, Bailey didn’t realize she had an uninvited audience member—Elie. 

He was walking behind the two women and learning all about Bailey’s relationship with her ex, which isn’t a typical meet-cute, by any means. What happened next was even more surprising: Elie gave Bailey some relationship advice that would change the course of their lives forever.

He advised her to “get rid of that guy” and referred to him as a “loser.” Then, as fate would have it, Elie and Bailey ended up at the same party. However, the two failed to exchange numbers that night—so Bailey found Elie on social media and slid into his DMs. They dated for a bit, but he wasn’t ready for a serious commitment—yet. 

Despite temporarily parting ways, the spark didn’t go out between them and after Insecure ended filming for its final season, Elie decided to shoot his shot one more time with Bailey. This time, he was the one to message her on social media, sure he had “found his person.”

Jean Elie and Randal Bailey theGrio.com
Photo: Sara Popovic

This engagement news may come as a surprise to some Insecure fans because Elie’s character, Ahmal, was openly gay. However, as Elie previously explained to many fans (and thirsty DMers), the persona was simply a function of the role, as he identifies as heterosexual. In fact, as he told The Advocate in 2020, he partly modeled his interpretation of Ahmal after a close friend and his boyfriend, saying, “I want my relationship with my girlfriend to [mirror] their relationship because their relationship is so dope.”

While keeping his romance with Bailey primarily private for years, news of the couple’s engagement is very public. Elie even shared the moment on Instagram, which got major love from Insecure co-star Amanda Seales, who commented, “AYYYYEEEE!!!!” 

The engagement news also comes just after the debut of the trailer for Elie’s upcoming dark comedy series on ALLBLK, Send Help, set to premiere on Thursday, August 11. Elie is both lead actor and co-creator of the half-hour dramedy, which, according to a press release, follows character “Fritz Jean-Baptiste (Elie), a first-generation Haitian American actor who is on top of the world, since landing a starring role on fictional hit TV show, This Can’t Be Us…all while being the sole support system for his incredibly demanding Haitian family, reeling from a recent tragedy.”

“I am extremely excited to finally share this series with the world, as it’s been a labor of love for the last several years. As a first generation Haitian American, I was honored to bring this, first of its kind, Haitian American story to the big screen,” said Elie in a statement. I’m so grateful to the community of dedicated creators that are bringing Send Help to life. From the writer’s room, to the incredible cast, to everyone behind the scenes—we can’t wait to bring you along Fritz’s journey to figuring out how to get out of his own way.” 


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