When a man is not really gay but is extremely awkward around women, becoming nervous, tongue-tied etc. like the way Gilligan would react to Ginger on "Gilligan's Island"
Last night at the bar this really hot chick was hitting on my friend Steve, but he got all Gilligan Gay on her and totally blew it.
When one uses one's big toe (right or left should work in an equally fine manner. Just choose your favorite!) to penetratethe anus of his or her partner.
Both big toes is called a coconut creme pie.
"If Steve really loved me, he'd bake me a long, jagged coconut creme pie until the early hours of the morn', but he's just been passing me the sloopy gilligan for like, two weeks. Guess I'd better kill myself. *raises noose*"
1)to spend time with beautiful women coming on to you with no possible consequences (it was the sixties), and yet avoid getting laid for seven years. I mean, WTF?