1. Tyra Banks and Will Smith
Before he married Jada, rumor has it that the two stars of Fresh Prince of Bel-Air famously dated while on the show.
2. Rihanna and Shia LeBouf
In 2007 before either of the two became household names they went on one date together but decided not to pursue anything due to lack of chemistry.
3. Tupac and Madonna
Madonna has said that she used to date Pac in his early days. We’re not totally sure if Pac would define it as dating but…
4. K. Michelle & Idris Elba
The reality star famously went on a media spree detailing the relationship between she and one of Hollywood’s most desirable bachelors. She even went so far as to release a video inspired by their relationship.
5. Rihanna and Leonardo DiCaprio
Although not confirmed the rumor mill has been swirling since the famous stars were seeing leaving the same venues together.
6. Michael Ealy & Halle Berry
After her breakup with Michael Ealy in 2005, Halle Berry told Instyle “I will never, never get married again.” Gaining perspective on their summer fling, she added, “After my last relationship [with Michael Ealy] broke up I was feeling like, well, it wasn’t that I didn’t want to be in a relationship, it’s just that I thought it would be okay to be on my own.”
7. Meagan Good & Joseph Gordon-Levitt
Meagan Good and Joseph Gordon-Levitt reportedly dated for six months in 2004 after meeting on the set of Brick. These days, Meagan is married to DeVon Franklin and Joseph is still single.
8. Joshua Jackson & Rosario Dawson
Joshua Jackson dated Rosario Dawson for about a year back in 2002.
9. Gabrielle Union & Ludacris
These two reportedly dated back in 2007 for a while and was her first serious romance since her split from her husband Chris Howard in 2005.
10. Kylie Minogue & Lenny Kravitz
Kylie Minogue and Lenny Kravitz made quite the attractive couple in 1991, and to say time has been good to the two is an understatement!
11. Shemar Moore & Toni Braxton
Shemar Moore dated Toni Braxton in the early ’90s, even appearing in her music video for her song How Many Ways. But the hot couple reportedly only lasted about a year — they were done by 1995.
12. Jessica Biel & Derek Jeter
Before there was Minka Kelly, there was Jessica Biel! Yankee stud Derek Jeter and Jessica Biel were spotted getting cozy in 2006, but the athletic couple didn’t last long — they were done by 2007.
13. Eddie Murphy & Toni Braxton
Eddie Murphy and Toni Braxton reportedly started dating each other in 2012. Reportedly is about all there was to it. Eddie finally set the rumor straight but stating they were just friends.
14. Seal & Tyra Banks
Tyra Banks dated Seal, 11 years her senior, back in 1996. Though the two made a cute pair when they showed up together at the Essence Awards, their romance lasted less than a year.
15. Danny Wood & Halle Berry
Who couldn’t resist New Kids on the Block back in the day? Certainly not Halle Berry! The Oscar-winning actress dated New Kids on the Block singer Danny Wood all the way back in 1989.
16. Diddy & Sienna Miller
Diddy and Sienna Miller kicked the romance rumor mill into overdrive when the party pals were spotted looking cozy at a number of events in 2007, including a lavish party in Ibiza when he reportedly escorted her back to her hotel room at 9 a.m.
17. Jada Pinkett Smith & Wesley Snipes
Long before she became Mrs. Smith, Jada Pinkett reportedly dated Wesley Snipes in the ’90s. The two even made a formal public appearance together at the 21st Annual AFI Lifetime Achievement Awards honoring Liz Taylor in 1993.
18. Rashida Jones & Mark Ronson
Rashida Jones got engaged to celebrity music producer Mark Ronson in February 2003, when he reportedly popped the question using a custom-made crossword puzzle that spelled “Will you marry me?” But the sweet gesture wasn’t enough to keep the attractive couple together — they broke up about a year later, but remain good friends.
19. Kim Kardashian & Nick Lachey
Back when Kim Kardashian wasn’t a household name, she briefly dated Nick Lachey after his highly publicized divorce from Jessica Simpson in 2006. Lachey even brought her to a screening of The Da Vinci Code, an official outing for the couple.
20. Tobey Maguire & Rashida Jones
Tobey Maguire and Rashida Jones dated in 1997. They lasted a solid three years before calling it quits in 2000 — right before Maguire became a household name thanks to Sam Raimi’s Spider-Man.
21. Thandie Newton & Brad Pitt
Brad Pitt dated Thandie Newton in 1994 when the two met filming Interview with the Vampire. The gorgeous couple broke up after a year, but reportedly still remain friends.
22. Minka Kelly & Donald Faison
Minka Kelly dated actor Donald Faison for about a year from 2004-2005.
23. Marlee Matlin & John Stamos
John Stamos reportedly dated Oscar winner Marlee Matlin in 1989, when the two were routinely photographed holding hands. They’ve obviously remained good friends, as Matlin recently tweeted a photo of the two hugging with the caption, “Mr. @johnstamos gives good hugs.”
24. Tiger Woods & LeAnn Rimes
Tiger Woods reportedly dated LeAnn Rimes in 2002. According to an Us Weekly source, the relationship ended when LeAnn’s dad thought Tiger, seven years her senior, was too old for her at the time.
25. Fergie & Justin Timberlake
Cougar Alert! Fergie dated Justin Timberlake when she was 23 and he was just 16 years old.
26. John Stamos & Paula Abdul
Paula Abdul dated “Full House” heartthrob John Stamos in the early ’90s.
27. Wesley Snipes & Jennifer Lopez
Clearly, J. Lo has a thing for bad boys! Jennifer Lopez was linked to her Money Train co-star Wesley Snipes briefly in 1994.
28. Usher & Naomi Campbell
These two dated for a few months back in 2005. There are conflicting reports about why they split and who dumped who.
29. 50 Cent & Vivica A. Fox
They dated back in 2003. He said for a year, however, Vivica said it was only for a month or so.
30. Taraji P. Henson & Common
Taraji has been linked with many handsome men, mostly her co-stars. She adamantly denies all the rumors but Common. They met when they were working on the ‘Testify’ video together. It didn’t work out but they are still friends.
31. Omar Epps & Sanaa Lathan
They met while filming Love and Basketball. They were together for around 3 1/2 years.
32. Kim Kardashian & Nick Cannon
Long before he was father to “dem babies” with wife Mariah Carey, America’s Got Talent host Nick Cannon dated Kim Kardashian. The two briefly dated for a couple of months in late 2006.
33. Ray Liotta & Jill Marie Jones
Reportedly, Jill Marie Jones & Ray Liotta had a steamy six month affair way back in the day. However, at the time of their romance she was living in California and he was on the East Coast. So, this is a maybe but probably not.