Who Has Chloe Bailey Dated?

Like her mentor Beyoncé, Chloe Bailey seems to believe in keeping her work life separate from her personal life. She’s consistently kept the details of her dating life and relationships under wraps. But, as is the case with so many celebrities, some information has managed to come up. Here’s everything we know about who Chloe Bailey has dated.

Chloe Bailey of Chloe X Halle
Chloe Bailey of Chloe X Halle performing at an event in December 2020 | 2020 Billboard Women In Music/Getty Images for Billboard

Chloe Bailey’s dating history, revealed

In the time since she broke out in 2016 as a member of Chloe x Halle, Bailey has only been linked to one person. She sparked rumors in 2019 that she was dating Diggy Simmons, whom she met when they were cast as love interests on Freeform’s Grown-ish.

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The rumors emerged that August when she and Simmons were photographed at a Dave & Busters and were allegedly seen kissing. Neither of them ever confirmed anything, but the speculation continued for months, especially after Halle Bailey hinted on Instagram Live that the singer had dated an unnamed Grown-ish co-star.

But by the following year, the rumored romance was over

Breakup rumors surfaced after the June 2020 release of Chloe x Halle’s second album, Ungodly Hour, where Bailey repeatedly called out an ex.

A lot of the speculation came from the song “Busy Boy,” which features lyrics about a two-timing boy with a baby on the way. Simmons had previously rapped in the 2018 song “Momma Love” about being told he’d impregnated an unnamed woman. But it doesn’t appear he ever commented on it after that.

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Chloe was eventually asked whether the song was created from actual experiences in an Instagram Live interview with Alabama radio station 95.7 Jamz. In response, she said:

“What I love about creating music is that we can put our experiences in the music and that’s how we share our personal life and it’s fun because that’s how our fans can kind of see what we’ve been dealing with. But yeah…”

Halle chimed in, “Well, a lot of the themes — or half of them are about being in love and being happy with that. And half of them are about what happens after the love, after your heart is broken. So some of our experiences were inspired by what had happened to us. So talking about ‘If you break my heart. I will do this to you. Just letting you know.’”

But there’s no official confirmation that the songs were about Simmons.

What’s Chloe Bailey’s relationship status now?

While participating in a Q&A session on Instagram Live in January, Bailey confirmed she’s still single. Asked why, Bailey said she’s simply enjoying life as a single woman.

“I’m single by choice, my love and that is because right now, I’m focusing on myself,” she explained. “I’m in my primetime of my life. And I don’t know… whenever the right one comes along or if they’re here and I don’t know it yet, then that’s what happens.”