The Hook Up: Diddy (then Puff Daddy) and J Lo met in 1999 and engaged in a whirlwind romance that lasted for nearly two years.
The Break Up: J Lo reportedly initiated the breakup with Puff as a result of the negative press that the pair earned as a result of the Club New York shooting that Puff and his artist Shyne were involved in in 2001.
The Mess They Left: This breakup left a lot of gossipmongers wondering, 'What could have been?' Despite going through several high-profile relationships, Diddy has never married. And as recently as this year, he's said that he still loves J Lo. And who can forget his "All I touch is J Lo's" line from the recent "O Let's Do It" remix?!
The Hook Up: Though they never officially came out as a couple, Chris Breezy and Rih-Rih started dating sometime in early 2008 and appeared out in public together many times.
The Break Up: You know the story by now. Chris and Rihanna were involved in an episode of domestic violence in January 2009 that was so tragic that it changed both of their legacies foreve
The Mess They Left: CB will probably never live down the incident that took place just before the 2009 Grammy Awards. Unfortunately, neither will Rihanna.
The Hook Up: After meeting through record executive L.A. Reid in the summer of 2005, Bow Wow and Ciara started dating seriously, recorded the hit single, "Like You," and even appeared on the cover of the November 2005 issue of VIBE together.
The Break Up: Reps for both artists said the split was amicable. But some speculated that Ci-Ci broke up with Bow after she spotted him cavorting with another female in Los Angeles in early 2006.
The Mess They Left: A year's worth of "Do you miss Ciara?" questions for Bow Wow and a steady stream of constant comparisons between his new flavors of the month and the R&B singer. Good grief.
The Hook Up: The-Dream wasn't Milian's first celebrity boyfriend. She met Cannon during the filming of the 2003 film, Love Don't Cost A Thing, and dated him for more than two years.
The Break Up: Milian reportedly found out Cannon was cheating on her in 2005 and dumped him. Cannon later insisted that he never wanted to get into a serious relationship with her in the first place.
The Mess They Left: From her relationship with Cannon to her relationship with hip-hop producer Dre to her relationship with The-Dream, Milian has become—fair or not—a sympathetic figure when it comes to celebrity relationships.
The Hook Up: The St. Louis rapper and the R&B starlet met at the MTV Video Music Awards in 2003 and started dating secretly shortly afterwards.
The Break Up: Amidst reports of Nelly cheating, the hip-hop power couple split sometime during the summer of 2009. But they revealed very little about their relationship publicly.
The Mess They Left: You could make the argument that both former superstars saw their stock plummet in the music industry as a result of their relationship. Because neither of them acknowledged much about their personal life, they've both been off the scene for a few years now.
The Hook Up: Before Wayne broke out in a big way in 2005 thanks to his album, Tha Carter II, he started a relationship with the Baddest Bitch that lasted for about a year.
The Break Up: Some rumors say Trina had a miscarriage during their relationship. Others say Wayne was starting to spend more time on his career. Whatever the case, the couple called it quits in 2006.
The Mess They Left: Post-relationship, both Weezy and Trina struggled to find love. Wayne started "dating" a number of girls, including Karrine "Superhead" Steffans, and Trina fell into the arms of NBA star Kenyon Martin. But none of the relationships have worked out for either of them.
The Hook Up: After meeting in the late 1990s, Swizzy and Mashonda got hitched in 2004 and had their first and only child Kaseem Dean, Jr. in January 2007.
The Break Up: This breakup was serious. Swizz apparently began an extramarital affair with R&B superstar Alicia Keys in late 2007 and split from his wife in April 2008. The two were officially divorced earlier this year.
The Mess They Left: Didn't you read last week's VIBE.com cover story with Mashonda? If not, READ IT NOW. It's the very definition of "messy."
The Hook Up: The rap star and the R&B starlet began dating in 2003 and were married in 2005, making them the biggest hip-hop power couple of the pre-Jay-Z and Beyonce era.
The Break Up: Another super messy breakup. Kelis filed for divorce from Nas in April 2009 citing irreconcilable differences—when she was pregnant with the couple's first child, who was later born in July 2009. Their divorce was made official less than two months ago.
The Mess They Left: A huge one. Nas and Kelis continue to battle in court over how much spousal and child support the rapper should be paying every month.
The Hook Up: Dupri and Jackson met sometime in 2002 and began dating shortly afterwards.
The Break Up: Following the death of her brother Michael Jackson, Janet announced that she and Dupri had split amicably.
The Mess They Left: These two actually remain on pretty good terms (at least, from what we've seen). But let's hope JD found out a way to cover up that strange "Janet as the Virgin Mary" tattoo that he got done on his torso just a few months before she pulled the plug on the relationship. Ouch.