Be careful about lying to someone about you having an STD.  You might just end up like 71 year old Thomas Redmond of California, who just had his appeal denied, after a jury found him responsible for $6.75 million for infecting his ex-girlfriend with herpes.  Yeah, it even sucks to be millionaire sometimes.

Redmond infected his ex-girlfriend with herpes after telling her he's "clean." Long story short, she sues him for $6.7 million dollars for physical damage, emotional distress and medical bills past and current. Nothing says unprotected sex like herpes, and nothing says "F*&$ You" like a $6.7 million lawsuit for giving someone herpes after you said you were clean.

This wasn't the only multimillion dollar lawsuit of it's kind though.  The most famous cases include Tony Bennett, who was sued for $90 million for infecting a partner with herpes in 1985; Robin Williams, sued for $6.2 million in 1986; and Michael Vick, sued for an unknown sum in 2005. Williams and Vick settled out of court. Bennett produced medical records claiming he did not have herpes, and countersued for defamation for $100 million.

ABC News