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In several 12-step fellowships, it is generally looked down upon and discouraged (not by everyone) to sleep with someone under a year clean, especially if you have over a year clean. The loophole refers to catching the "newcomer" before he/she even gets clean, therefore providing a valid excuse for the incident(s) to be perfectly moral and justified.
Yo man, I'm thinking about trying to fuck Sheila, she's only got like 37 days though..." --"Definitely do it, who gives a shit what people say, that's 37 days too many in my opinion. I just fucked a girl who had zero days a few nights ago, real talk." "Word, that's awesome - you found the loophole.
loophole by pure insistence April 3, 2011
A part of scripture that works really well where u can get him off without going to hell
Cause The Bible says premarital sex is wrong
But Jason says that guys can't wait that long
(but there's a loophole)
The act of penetrating the anal instead of vagina in order to keep an women's virginity.
Nic: Man I just loopholed a bitch

Minx: Nice!
Loophole by Dollardolbey13 April 20, 2017
A sexual position where the female contorts her body so that her vagina is over her head.
Last night I was fucking this bitch, and she hit me with a Loophole ;)
Loophole by pam666 May 29, 2017
The policy doesn't saying anything about taking the pictures of staff. Or anything about using the pictures they took of themselves.
I found a loophole. It was easy.
Loophole by Hym Iam December 30, 2020
When the bong bowl doesn't pull through fully and you can't take out the remaining weed; so you must light and pull through.
"Why is there a loophole still in my bong?"
loophole by Trple G July 28, 2021