He was a player back in his 'Justified' days
Post-Britney Spears, Timberlake has generally refused to discuss his personal life with the media, as a result of which his relationships have been the subject of much speculation in the tabloid and celebrity press. Prior to Spears, he was briefly romantically involved with Beyoncé Knowles[107] and singer-actress Stacy Ferguson.[108] He was romantically linked with Janet Jackson (in July 2002),[109] actress-dancer Jenna Dewan (in mid-2002),[109] and actress-singer Alyssa Milano (between September and October 2002).[109] Timberlake began dating actress Cameron Diaz soon after they met at the Nickelodeon Kids' Choice Awards in April 2003. Regular rumours of break-ups reported in the tabloid press were either ignored or occasionally denied.[110][111] On the December 16, 2006 episode of Saturday Night Live, Diaz introduced Timberlake as the night's musical guest, and the couple officially split shortly afterwards. After the tabloid press alleged an affair between Timberlake and Scarlett Johansson, with whom he had shot the video for his single "What Goes Around.../...Comes Around Interlude",[112] Diaz and Timberlake issued a joint statement on January 11, 2007:[113] Later in January 2007, Timberlake was linked to Jessica Biel when pictures surfaced of the two snowboarding in Park City, Utah during the Sundance Film Festival.
source: en.wikipedia.org/wiki/Justin_Timberlake