What is Shawshanking?
1.
To slowly chip away at getting to know someone in order to get into a relationship with them, in the way Tim Robbins' character slowly chips away at his prison cell to eventually brreak out of jail in the movie The Shawshank Redemption.
"Ray's a bloody shawshanker! He's been shawshanking my girlfriend for the past three months!
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2.
When you are stuck in a miserable job, working for the devil (aka - the warden) and you slowly start to chip away at your escape while plotting to take the boss down when you leave.
"How do you put up with that bitch on two legs?"
"Don't worry about me...I'm
shawshanking ."
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