a descriptive phrase for attempting any hopeless task. If you've ever tried to push water uphill you'll understand the concept.
literal-Part of my job involves clearing water from the floor of my work station. Because the floor is pitched away from the drain, it takes an inordinate amount of time to clear the water, because I'm always pushing it uphill.
figurative-Asking your boss for a raise in these times of tight money makes as much sense as pushing water uphill.
by earpuller January 16, 2006
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This is a phrase you say when everything is going your way - things are looking up - there are challenges ahead but it is looking more and more likely that you will be able to overcome them. It can also be used as an action phrase - "time to get the ball rolling uphill".
"Looks like we finally got approval for our innovative but risky product! The ball sure is rolling uphill!"

You actually don't have to take that test today! The ball is rolling uphill!

We really need to get the ball rolling uphill if we are going to get done on time.
by mad rat April 12, 2023
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Trying to do the near impossible due to having or being given the wrong tools or insufficiency of time.
Usually preceded by "like pushing...".
The refusal of management to see the blindingly obvious despite it being pointed out and insisting upon something inappropriate.
A:"Can you get this new program to print?".
B:"No, I've told the service centre every day this week but they still say it's ok; dealing with them is like pushing diarrhoea uphill with a rake".
by MoLincs September 20, 2009
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When you are banging a girl while standing up that is taller than you.
Tom: "I'd hit that standing up."
Steve:"How? She's like a foot taller than you."
Tom: "Easy. I'll be fucking uphill!"
by Djsparty May 11, 2010
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A person that thinks they are always right and others are wrong
Uphill Stanley ran uphill and anyone that runs downhill is wrong
by Yelnats May 23, 2020
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The act of chilling with your significant other and continuing to have hardcore sex with them to the point where they disintegrate and spawn at a place of higher elevation
Yo, did you chill uphill with Brianna?
Yeah dude she said she ended up on hieters hill!
by captain swaggy December 17, 2015
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