Key Takeaways
- Chelley Bissainthe and Ace Greene’s split left "Love Island USA" fans heartbroken.
- La La and Carmelo Anthony’s divorce showed that even long-term love stories can come to an end.
- Usher and Chilli’s breakup, along with Nick Cannon and Mariah Carey, sparked major online conversations long after they called it quits.
Thanks to the internet, we follow our favorite celebrities so closely that we end up invested in everything they do: how they’re spending their time, what they’re working on, and, more strangely, who they’re dating. Just like the couples we know in real life, plenty of stars across music, sports, and entertainment have dated and later split. Whether we wanted to admit it or not, we enjoyed seeing them with that person and got used to them being together.
Take “Love Island USA” Season 7 couple Michelle “Chelley” Bissainthe and Ace Greene, who announced their breakup in December 2025, as one example. Going back a bit further, there are iconic couples from the 2000s and 2010s, like Usher and TLC’s Chilli, and Nick Cannon and Mariah Carey.
In putting this list together, we chose couples who mostly parted on good terms, stayed friends afterward, or didn’t publicly share why (because, as much as we’d like the details, not everything is everyone’s business). Without further ado, here are 10 celebrity breakups that left fans feeling a bit heartbroken.
1. Michelle “Chelley” Bissainthe and Ace Greene
“Love Island USA” is responsible for matchmaking some of the cutest couples we can think of — Serena Page and Kordell Beckham, as well as Olandria Carthen and Nicolas Vansteenberghe, for starters — but to be fair, most of them don’t last. Although, considering Chelley and Ace happened to meet a month before appearing on Season 7 (and the fact that we dedicated a round-up to their cutest couple moments), it was a bit of a heartbreaker to learn they’d split.
“It really was a tough decision for the both of us and very hard to decide, but, you know, when you love someone, sometimes loving someone means letting go,” Chelley said in an interview with SiriusXM’s Page Six Radio, after announcing they had “decided to part ways.”
2. La La and Carmelo Anthony
After watching La La walk viewers through nearly every moment leading up to her wedding day on “La La’s Full Court Wedding,” it was a bit of a shock that her marriage to Carmelo Anthony didn’t go the distance. The former couple tied the knot in 2010, followed by her filing for divorce in June 2021 due to “irreconcilable differences.”
As La La later recounted on Alex Cooper’s “Call Her Daddy” podcast, Melo being traded to the New York Knicks in 2011 was "the start" of their unraveling. “Things got tough with New York, just constantly being under the spotlight and people watching every little thing,” she explained. On the bright side, the two welcomed their son, Kiyan, who turned out to be an incredibly talented baller.
3. Michael B. Jordan and Lori Harvey
“You can meet the right person, and be at the wrong time, and it just doesn’t work out,” Michael B. Jordan told GQ in 2025. While we may never know who he was referring to, the Creed actor’s love life update came a little over two years after he and Lori Harvey split. According to sources, the pair just weren’t on the “same page,” and that’s completely okay.
That said, with both of them ranking on REVOLT’s sexiest men and women alive lists, plenty of us would’ve loved to see them continue as the hottest couple around.
4. Big Sean and Jhené Aiko
We always pictured Big Sean and Jhené Aiko growing old the way they do in the “I Know” video. While it’s never too late for that to happen, the “Beware” collaborators once called it quits in 2019, followed by him releasing “Single Again.” As you can imagine, the internet was devastated, mostly because they had been such a great rap-R&B pairing, and it could have derailed plans for a sequel to TWENTY88.
The artists did fortunately find their way back to each other the following year, with Aiko welcoming their first child together, Noah, in 2023.
5. Taraji P. Henson and Kelvin Hayden
Taraji P. Henson and Kelvin Hayden were so close to tying the knot, and had they not needed to postpone their wedding due to the COVID-19 pandemic, it’s possible they would’ve made it down the aisle. Unfortunately, the couple decided to split two years after he proposed, even after doing “the therapy thing.”
“I’m dedicated to the Black man, y’all. I just turned 50 and I mean, I hadn’t said it yet, but it didn’t work out,” Henson said on “The Breakfast Club.”
6. Wiz Khalifa and Amber Rose
In her own words, Amber Rose and Wiz Khalifa were “very immature” when they got married in 2013. Due to outside factors like fame and their families, the two divorced just a few years later. That being said, Rose has described them as “best friends,” and they definitely gave us some unforgettable couple moments.
“I think that me and Wiz are [such] best friends now that... we’re so far past being in love that I can say that now, right? It’s not like anything that we would circle back to or anything. We’re just friends and co-parents,” Rose said on the “Tamron Hall Show.” Like several other former couples mentioned here, they share a son: Sebastian.
7. Mariah Carey and Nick Cannon
Nick Cannon and Mariah Carey’s many red carpet moments — and their super adorable Halloween costumes — always come to mind when we think about their relationship, which saw them marry in 2008 and file for divorce in 2014. Their divorce was finalized in 2016. Thankfully, those six years also gave them a family. They welcomed twins, Moroccan and Monroe, during their marriage.
8. Usher and Chilli
If “R&B power couple” had a textbook example, Usher and Chilli in the early 2000s would probably be the photo you’d see. The TLC singer popped up in his “U Remind Me” and “U Got It Bad” videos, they attended the Grammys together, and then, for reasons still not fully known, they split in 2003.
Even though people love insisting Confessions was about her, Chilli told Us Weekly that they “were together when he recorded that album.” She also said she’ll “always love” Usher. Fun fact: the Grammy-winning musician proposed before they ultimately went their separate ways, so who knows how different things might’ve been if they had tied the knot.
9. Serena Williams and Common
Having starred in his “I Want You” video in 2007, Serena Williams and Common dated until around 2010. Years later, during an interview on “The Meredith Vieira Show,” Common joked that they had a “mutual breakup, but she initiated it.” He added, “We got a great understanding, and I care about her as a person.”
It was good while it lasted, and thankfully, both Common and Williams have moved on to new chapters in their lives.
10. Solange Knowles and Alan Ferguson
Although Solange is one of the more private celebrities mentioned on our list, her — and probably all of the Knowles family’s — love life is something people have always been invested in. After getting married in 2014, the “Cranes in the Sky” artist shared that she and the music video director decided to call it quits five years later. In an Instagram post, Solange wrote, “11 years ago, I met a phenomenal man who changed every existence of my life. Early this year, we separated and parted ways.”