Cameron Diaz and Justin Timberlake
In 2003, after Justin’s infamous breakup with Britney Spears, Justin Timberlake began dating actress Cameron Diaz, who was eight years his senior, which in Hollywood might as well be a lifetime. The two were one of the most popular couples in the tabloids, but the ended up breaking it off in 2007. She is now married to Good Charlotte band member Benji Madden and Timberlake is married to actress Jessica Biel.
Michael Keaton and Courteney Cox
Courteney Cox is best known for her role as Monica Geller on beloved sitcom Friends. Before she was a household name however, she dated actor Michael Keaton, 13 years her senior. They two were together for six years, breaking up in 1995. She then moved on with David Arquette, who she ended up marrying and later divorcing. She is currently linked to Snow Patrol band member Johnny McDaid.