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The Friday Night Dilemma 

When your with your friends on a Friday night, and walk around town hopelessly in search of something to do. It usually ends in failure, making everybody wanting to go home hoping tomorrow will be a better day. Worse of all, its a complete waste of your Friday night
Boy 1: Shit dude, we're stuck in the Friday night dilemma again.. WHAT CAN WE DO!?"

Boy 2: How about we go over my house and play COD?"

Boy 3: Fuck COD dude, If i wanted to stay in tonight I would've.. how about we walk over down to the mall and try to get some girls? Maybe we'll get lucky!

Boy 4: Screw your shit, we did this last week. Listen, I'm going home, tonight fucking sucked.

Boy 1: OH COME ON! Listen, how about we smoke some of my bud and we'll go watch a movie at my place?

Boy 2: Fuck it, I don't even want to. Tonight sucks and you know it, peace bro.
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The Diceman 

When you ejaculate in a girls hair and then slick it back. Then follow up with sayin "OHHHH!" (like Andrew Dice Clay)
I fucked this broad the other night and made her look like the DiceMan "ohhhhhhh!"
Related Words
Indicates an individual who has as many personalities as the possible outcomes of rolling a dice. He/she/they can be your friend, ally, enemy, dictator, delusional to reality human, etc. He/she/they have a ‘hidden’ agenda which is very transparent. In this person’s head you have a specific role to play and should stick to it without challenging the status quo.
Saw the diceman today, he’s in a good mood today. I’m not sure how long that will last before he rolls his personality dice again…
Diceman by Bettyboo22 August 22, 2021

Pride/Shame Dilemma 

A situation where you feel deeply proud of an action only to realise that the act, however magnificent or unique, cannot be shared with others without revealing something private and shameful.
He emerged from the public restroom feeling liberated and youthful. His mind often returned to the girthy behemoth that he'd left behind. He reflected with pride at how much of his product was above the waterline. His reverie was cut short by the realisation that despite his Herculean effort, this was far too shameful to share with his friends.

"What are you thinking about?"

He smiles, gazing fondly into the distance before dropping his head, feeling the full weight of his pride/shame dilemma, and quietly muttered,

"Nothing"

bishop's dilemma 

bish-uhp's di-lem-uh

n. a type of piercing of the penis that penetrates the Urethra, rusulting in multiple streams
Check out that guy's bishop's dilemma! Oh shit! He got himself in the eye.

dilemmanade 

When life gives you dilemmas, make dilemmanade.
dilemmanade by Omar O. Ungh January 21, 2011

roy's dilemma 

Everything was going great at the orgy until I was faced with Roy's Dilemma.
roy's dilemma by The Reverend Roysus September 30, 2013