Un-Break Our Hearts: Couples We Hoped Would Last

Weezy and Toya, Diddy and Kim and more.


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Jesse Williams and Aryn Drake-Lee - Tabloids would be out of business if it weren't for celebrity breakups, but there are a few A-list couples we wished stayed together.This is definitely the most shocking split of the year (so far!). After five years of marriage, two kids and being together for a total of 13 years, Jesse Williams filed for divorce from Aryn Drake-Lee. Sadly, the divorce has already gotten messy with the former couple in a custody battle.  (Photo: John Shearer/Getty Images for GQ Magazine) 


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Brad Pitt and Angelina Jolie - They seemed to be happy in love — but there was always a side-eye at this relationship because, as legend has it, Brad hooked ip with Angelina while he was still married to Jennifer Aniston. Nonetheless, Brangelina were Hollywood's hottest couple. They were together since 2006, married in 2014 and Angelina filed for divorce in 2016.  (Photo: Anthony Harvey/Getty Images) 


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Safaree Samuels and Nicki Minaj - Safaree Samuels and Nicki Minaj were hip hop's hottest couple for years. They were together one and off for 12 years and reportedly colloborated on her 2014 album The Pink Print. However, they broke up that same year. Samuels was by her side during her intense rise to superstardom, no one saw that break up coming. (Photo: Astrid Stawiarz/Getty Images for Mercedes-Benz Fashion Week Spring 2014)

Toya Wright and Lil Wayne - Meeting when they were just teenagers, Toya and Weezy welcomed a daughter, Reginae Carter, in 1998. They made it official in 2004, but divorced just two years later. In 2011, Toya married entrepreneur Mickey "Memphitz" Wright.  (Photos from left: Rick Diamond/Getty Images, Jason Merritt/Getty Images)

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Lil Wayne and Toya Carter - Lil Wayne and Toya Carter are one of those couples. The YMCMB rapper and the Tiny and Toya star were high school sweethearts and welcomed daughter Reginae Carter when they were just teenagers. They married on Valentine's Day 2006 but divorced just two years later. Still, the couple stayed on good terms for the sake of their daughter and even became friends again. "He always keeps a good friendship with me no matter what," she says. "He's a great man."(Photos from left: Rick Diamond/Getty Images, Jason Merritt/Getty Images)

Grammy Winner - In 2003, Badu won her fourth Grammy, this time for "Love of My Life (An Ode to Hip Hop)," featuring Common. She's been nominated for more than a dozen Grammys throughout her career.(Photo: Evan Agostini/Getty Images)

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Common and Erykah Badu - When a politically-conscious rapper and a neo-soul queen get together, they're bound to make beautiful music. That's exactly what this couple did on their ode to hip hop, "Love of My Life." Sadly, they broke up in 2002 after two years of dating, and according to Common, it didn't end well. "She called me and was like, 'Hey, I don't want to be in this relationship no more. I be liking somebody else,'" the rapper recalls. Surely, a breakup like that inspired some sad love songs.  (Photo: Evan Agostini/Getty Images)

Loves Me, Love Me Not - Kanye West was engaged to Alexis Phifer back in 2007. The couple attended various events together and appeared to be happy, but the engagement was later called off. (Photo by Thos Robinson/Getty Images for Island Def Jam Records )

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Kanye West and Alexis Phifer - Don't get us wrong, we love seeing Kanye with his self-proclaimed soul mate Kim Kardashian and their beautiful baby North, but sometimes we reminsce over the rapper's humbler days, when he was with former fiancée Alexis Phifer. There's no denying Yeezy was more grounded — though not nearly as entertaining — when he was with the fashion designer, who (as of now, at least), is the person who came closest to becoming Mrs. Yeezy. (Photo: Thos Robinson/Getty Images for Island Def Jam Records )


7 / 8

Regina King and Malcolm-Jamal Warner - This relationship never got its happy ending. King and Warner, who were child actors on 227 and The Cosby Show, respectively, seemed like a match made in sitcom heaven. The couple were happy for two years before Warner called it quits on King. "She's heartbroken," a friend said at the time of the split. "She really thought this would last forever." Sigh, so did we. (Photo: Stephen Shugerman/Getty Images)


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Chilli and Usher - This R&B power couple fulfilled many fans' fantasies when they got together in 2001. Though their romance ended in 2003 (reportedly because of Ush's repeated infidelities), the exes have dropped enough hints in the press over the years to have us believing they never fully got over each other. Considering their both single now, maybe it's time to give love a (second) chance?   (Photo: Evan Agostini/Getty Images)