Sex partner: Unidentified "boyfriend"
Year it leaked: 2009
The tape was made, reportedly, when Meester was 18-years-old, and the scandalous rumor about it was that she performed a sex act —can we say "foot job"? OK, a foot job—on the nameless boo. 

Real or fake?: Stills released from the tape suggest it's real, but we may never know, as the company trying to obtain it for distribution,, never closed the deal.