Happy Gilmored

Happy Gilmore is known for the way he takes 6-7 steps up to his golf ball before driving it further than humanly possible. Happy Gilmoring/Happy Gilmored piggy backs off this idea in that you take your fully erect penis and sprint right towards the bent over ass of the person you are trying to have sex with. The intent is to have your dick go further up the vagina/asshole than any other cock that has been in there in the past.

Dude: Yo man my chick drank so much and passed out leaning on the bed last night.

Friend: Did you do anything weird to her?

Dude: Weird? No. But I happy Gilmored the shit outta that ass. Got like 3 inches deep!

by Uncle Gary's Potato Farm May 18, 2017

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Freaky Gilmore

Happy Gilmore but instead his name is Freaky Gilmore.

And instead of playing golf, he puts golf clubs up his ass.

“Woah Momma, Now that’s what I call a Freaky Gilmore!!!”

by Skibiti Keiler April 27, 2024

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Happy Gilmored

To be happy gilmored is to have a golf ball thrown at your crotch, but you were unaware the other person had said golf ball. Especially when, but not limited to being hit in the balls specifically.

“Emma happy gilmored me”

by simonbeatles722 March 28, 2025

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Sad Gilmore

When you accidentally cut your ballsack open while shaving and a ball falls out.

Example:
Two friends catching up after a few days.
Friend 1: Dude where have you been? I haven’t heard from you in days.
Friend 2: Yea man I was in the ER for a few days after I suffered a Sad Gilmore.

by Munty Jelqmore May 23, 2024

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