When you're in the middle of two asses and don't know which one to choose first.
DRAMON: AYE YO NIGGA I WUZ KICKIN IT WIT DEEZ TWO THICK ASS WHITE BITCHES BUT THEN THEY PUT ME IN AN ASS DILEMMA AND I WAZ THEIR TRYNA FIGURE OUT WHAT ASS I WANNA FUCK FIRST, SHIT WAS SO HORD IT WUZ LIEK AN SAT UP IN DIS MUHFUCKA!

Tom: Whoa man that's sick, I 'm very intrigued!
by Cartah Hoffah December 16, 2015
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facing a choice between two equally undesirable alternatives
The lion was on the horns of a dilemma, deciding what he should do in such a risky situation.
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Angst experienced by most serial kidnappers, rapists and lorry drivers after spending some considerable time with their female abductee.
Sarah had spent the best part of six months chained to the radiator in the cellar. Bubba Lou was plagued by the fisherman's dilemma. 'Do I kill it, or do I let it go?'
by manoftrent November 28, 2017
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The known sentiment that there is a 50/50 chance of a word's definition on UD either being mildly amusing or critically unfunny.
Tom: Bro! I just looked up a word on Urban Dictionary

Michael: And as such you have fallen into the Urban Dilemma
by KeinDragon September 9, 2020
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The issue when you butter one piece of toast and the butter melts but when you proceed to the second piece it has cooled leaving you with a brick of butter
Tommy was sad due to the butter dilemma, now this will haunt him all day
by Switch Mane September 22, 2020
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aka. R.D.D. When an individual has a romantic crush on somebody, but does not know how to tell them how they feel about them. It often happens to people who have never asked someone out and has not been in a romantic relationship previously.
Alan: Hey Dima. What is the matter? You have not been yourself all day.

Dima: I have a romantic disclosure dilemma. I've had a crush on Kailani for months now and I want to ask her out before the semester is over, but I have no idea how to tell her how I feel about her.
Alan: You should go on Wikihow and look it up. They usually provide good advice on how to do stuff like that.
Dima: Thanks for the help. I'll try that.
by Vanguard 1998 February 27, 2021
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The situation one faces when deciding whether or not to stroke and if so, for how long. It is usually present when another more important activity should supersede stroking, but one wants to make time for stroking nonetheless. It is more commonly encountered during the day (when one has more to do) than at night for those who are not nocturnal.
I resolved my stroker's dilemma by affirming to myself that it's a normal and healthy activity - like eating or sleeping. I'll catch the next train.
by goyo May 2, 2017
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