Date of Fucking: January 2008
Pre-Fuck: Doing Things With NSYNC and Then Bringing Sexy Back on His Own.​
Post-Fuck: *Acting*

Justin Timberlake is probably the most famous man Lindsay Lohan has had sex with. Though not as well-documented as his relationship with Cameron Diaz or his marriage to Jessica Biel, here is one salacious and weirdly precise headline: "Justin Timberlake Lindsay Lohan Sex One-Night Stand January 2008." This busted website is the only one that comments confidently about the Lindberlake relationship: "According to an explosive scoop from Star Magazine, the bisexual vamp has been dishing dirt about seducing the attached 'SexyBack' star into a one-time intimate encounter last January to pals around Hollywood for months." An insider is quoted saying they did it on the couch, another detail we didn't ask for but… Thanks.