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1.
Gilwad is an acronym which stands for ‘Grandpa I’d Let Wine And Dine Me, Pay For Bigger Breast Implants, And Then Fuck Them Until I Come Silicone’. This term was first mentioned in the film Another Gay Movie.
Buffy: “Dude’s a fucking Gilwad, girl.”

Susie: “What a Gilwad, Buffy?”

Buffy: “G.I.L.W.A.D. Grandpa I’d let wine and dine me, pay for bigger breast implants, and then fuck them ‘til I come silicone.”

Tiki: “That is’a too’a many letter, Buffy. Does not’a add up.”

Buffy: “I am a cheerleader, Tiki. Not a calculator.”
by Lorenzo Kinderfeld August 04, 2007
 
2.
G.I.L.W.A.D, similar to milf Short for Grampa I'd let wine and dine me, pay for bigger breast implants, then fuck them till I cum silicone.
Dudes a fucking GILWAD, girl.
That GILWAD is coming over to us.
by Eggatha March 01, 2007