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1.
The ultimate homosexual sexual conquest. This is where a gay man seeks to have sex with a straight man because of its almost impossible nature. The Holy Nail can be two things. One, it's the journey and desire to have sex with a straight man. The other is the actual act of having sex between a gay man and a straight fellow.
Loren: "Gay guys really want to do straight guys. They're the Holy Nail."

Shelby: "So gay guys like to do other gay guys?"
Corrine: "Yes, but they would rather do a straight guy. You know, the Holy Nail."

Matthew: "Damn, you see Fred over there? He's looking fine tonight."
Seth: "Yeah, too bad he is with his girlfriend."
Matthew: "I know! He's my Holy Nail."

Keith: "If I finally nail a straight dude, would that be considered a Holy Nail?"
Caitlin: "Not sure, because if he has sex with you he might be gay."
Keith: "Yeah, then it wouldn't be a Holy Nail."
by Noullet776 November 30, 2013
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