Diggy Simmons and Chloe Bailey played on screen boyfriend and girlfriend on the show Grown-ish.
But was there ever any romance between them off screen as well?
When the show first aired in 2018, it didn’t take long for viewers to speculate if the pair’s chemistry was so good because the two actors were actually falling for each other in real life.
Are Diggy Simmons And Chloe Bailey Dating?
It’s not unusual for fans to hope that the people playing their favorite characters end up having a real romance, too.
And it’s also not unusual for that to happen.
Kirsten Stewart and Robert Pattison, Miley Cyrus and Liam Hemsworth, Ryan Gosling and Eva Mendes all met and fell for each other while they were on set.
According to PopSugar, it looks like that was also the case for Diggy and Chloe.
In August 2019, the co-stars were spotted having lunch together at Dave & Busters.
A source even told The Neighbourhood Talk that they saw them kissing.
A few months later, a video of Chloe and Diggy dancing at a Christmas party sparked more rumors that they’d started dating each other.
But if there was something going on between them, then they must’ve tried really hard to keep things under wraps.
Because the two weren’t seen in public again after that.
Halle Bailey Hints At Chloe’s Love Life
However, that following year, whispers of their alleged secret romance started to get louder when her sister Halle mischievously suggested something on an Instagram Live.
One of their followers asked them if they’d ever dated one of the other cast members of Grown-ish.
Halle looked at her sister and asked- “Chloe?”
Chloe looks back at her sister in disbelief and asks- “What?!”
Suggesting that it was not something that she wanted to talk about in the public eye.
The sisters have dropped hints about their love lives in their music.
Were Chole Bailey’s Lyrics About Diggy?
And there was one song from their 2020 album Ungodly that really got people’s tongues wagging.
Because Metro reported that Chloe was singing about one of her exes, who a lot of fans suspected was Diggy.
In the lyrics of the song Busy Boy, Chloe sings about a guy who is going out with a bunch of different girls at the same time.
Though there’s been no confirmation that the player was Diggy, the song helped fuel the fire that there could’ve been a fling between him and Chloe at one point.
It’s no secret that the Bailey sisters write their song lyrics based on the relationships, romances and important moments that they’ve gone through in life.
The Metro report revealed that Chloe once said that what she loved about creating music was that they could put their experiences in the music.
And that was how they’d share their personal lives.
She added that it was fun, because that way her fans could kind of see what they’d been dealing with.
But that means that there is also a lot of room for interpretation.
And since the two singers don’t often confirm or deny the gossip surrounding their songs, it’s up to the listener to decide if it’s true or not.
Will Diggy Simmons And Chloe Bailey Make Music Together?
Diggy and Chloe may have worked together as actors, but the pair have never made any music together.
But it’s reportedly not something that’s off the table either.
In an interview on the Kreative Klout podcast, Diggy said there was absolutely a possibility that he would collaborate with Chloe on music.
He shared that a lot of the Grown-ish cast members were pretty musical, and that they’d always be messing around on set, beatboxing, rapping and banging on tables together.
So he confirmed that there was a big chance that they’d one day make some music with each other.
Diggy Simmons And Chloe Bailey’s Relationship
What’s not clear is what kind of relationship Diggy and Chloe have now.
In an interview with Essence, Diggy gave his opinion on the different ways that a breakup can go.
He revealed that when relationships end, people never quite know how they are going to end.
He asked: “Can you just be cool or is it just this straight up, ‘No, we’re not good. We’ll never be good?’”
Since the rumored fling between him and Chloe, Diggy hasn’t really been seen with anyone else.
Diggy Shares Intimate Details About Type Of Woman He’s Looking For
When speaking with BET, he gave some pretty intimate details about the kind of person who he was looking to have a romantic relationship with.
He admitted that a dealbreaker for him would be someone who couldn’t navigate through different spaces.
Diggy explained that he would often find himself in different rooms, traveling a lot, and doing different kinds of work.
Which was why he was hoping to meet someone who he could bring along with him and know that they would be able to get along with people.
When he was asked if long-lasting love still existed, he confessed that he thought that it did.
Diggy said: “I think that if you find the right person and you’re able to focus on them, without having anything come between the two [of you], it’s possible.”
Chloe Said, ‘I’m One Thousand Percent A Hopeful Romantic’
Funnily enough, Chloe is reportedly still single now, too.
During an interview with COSMOPOLITAN, Chloe admitted that she was single at the time, and that she hadn’t seen anyone for almost a year by that point.
Her theory for her being single was that she was working on herself.
She explained that when people haven’t mastered the art of loving themselves, they question why others would love them.
Chloe went on to add that she couldn’t expect someone to love her wholeheartedly when she was not there yet within herself.
When asked what she was like when she was in love, she revealed that she was such a mush ball, and she loved cuddles.
She shared: “I want someone to be just as madly in love with me as I am with them. I’m one thousand percent a hopeful romantic.”
Her interview with COSMOPOLITAN wasn’t the first time she’d brought up her single status and understanding the importance of your self-worth
When speaking to E! News in 2022, she said that she was learning that self-love was the greatest form of love that someone could ever receive.
She added: “Any man who is lucky enough to come into my life will have to compete with that.”
Who Is Chloe Bailey Dating Now?
But is there a man in the picture?
The last time that Chloe was linked to someone was toward the end of 2023, when she was seen leaving a club with rapper Tyga, per the Daily Mail.
After they exited the venue, the duo got into a luxe black car together.
But they haven’t been spotted together since.
Chloe’s love life made headlines in 2022 when she was rumored to have dated Gunna.
According to J-14, she admitted that her song, For The Night, was written about the rapper.
She revealed that she knew she might regret saying it, but she confessed she could live with the secret being out there because it might help the song get streams.
Reportedly, she wrote the song after she heard Gunna speaking on an episode of the Breakfast Club.
In the interview, he denied the rumors that the pair were dating, by claiming that they were just really good friends.
But the lyrics of For The Night make it sound like they were more than just pals.
In the song, Chloe sang about laying on a man’s chest in her bed, and how she loved when he called her baby, and made her feel like his lady.
Chloe Bailey Speaks Out On ‘Boring’ Accusations
The Washington Post reported that Chloe recently came under fire for her reputation of being ‘boring.’
She addressed the claim by saying that she could never do enough.
She liked to keep her inner circle small and her business to herself.
Chloe claimed that the reason some people labeled her as uninteresting was because she’d keep certain things hidden and private.
The performer admitted that being boring was a good thing.
She stated that she didn’t take any illegal substances, or anything scandalous like that, and added that she’d much rather be boring.
The Washington Post also asked her to describe herself.
Chloe shared that she was a melting pot of things.
She said: “I am like this big burst of energy around the ones who make me feel the most safe. And my outlet for any frustration is my art.”
