When the dynamic sisterly pair Chloe x Halle initially gained notoriety for their YouTube song of Beyonce’s ‘Pretty Hurts,’ it was nearly unimaginable to anticipate that they would reach such heights of fame. Queen Bey herself signed them to Parkwood Entertainment a year later, in 2015.

Their pop-cultural impact has exploded since their debut release. The two young women have recorded two albums, multiple mixtapes, and EPs soundtracked a major motion picture, and joined the cast of the popular adolescent program Grown-ish in just five years.

Halle Bailey and Chloe Bailey are most known for their roles as the twins Skye and Jazz Forester in the hit drama. They’ve even performed the show’s theme tune and spent the last three seasons growing their fan following.

The Bailey sisters thrived under Beyonce’s tutelage, and they, like their instructor, believe in keeping their work and personal lives distinct. Halle’s love life looks to be non-existent, but Bailey, who is older, has a different story to tell.

Previous Relationships of Chloe Bailey

The ‘Do It’ singer appears to be quite private about her dating past and keeps her personal life hidden. In the past, she has deftly evaded probing questions, but reports of her alleged connection with fellow Grown-ish actress Diggy Simmons erupted in 2019 after they were sighted at Dave and Buster’s. During their date night, they were even seen kissing.

On the renowned adolescent show, the two had starred as the cutest pair. Despite the media attention, neither Chloe nor Simmons have commented on the purported romance.

Another time when Halle read a question on Instagram live, “Have you all dated anyone from Grown-ish in real life?” it sent fans into a frenzy. Chloe was dumbfounded as a result of this.

Following the release of Ungodly Hour, rumors about Chloe’s relationship grew even stronger, as the song’s lyrics appeared to be directed at a minor ex-boyfriend.

There were also breakup rumors following the release of the song ‘Busy Boy’ from the album Ungodly Hour, which has lyrics about an unfaithful lover set to become the father of another woman’s child. On his tune ‘Momma Love,’ Simmons rapped about getting someone pregnant in 2018, although it was never confirmed if the song was based on a true story.

However, there is insufficient information to draw any conclusions about what actually occurred.

The Single Life of Halle Bailey

Chloe x Halle went on an Instagram Live interview with Alabama radio station 95.7 Jamz after the release of their second album, Ungodly Hour. Chloe was asked if the songs were influenced by any real-life events during the interview, and she said yes.

The sisters also stated that they were both singles throughout the conversation. Halle admitted she was still unmarried while engaging in an Instagram Live Q&A session earlier this year, and when asked why she said this.

The Bailey sisters may be seen in season 4 of Grown-ish, which premiered on June 8.