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A really hard situation that is harder than any other problems ever encountered. A much more difficult circumstance than a hardship, which is more painful than just a plain difficult situation.
1 - "Man, dating 5 girls at a time is the hardestship I've ever had!"
2- "Your Public Speaking final might be hard, but that Calculus final will be the hardestship you'll ever face!"
by austinhaws December 15, 2008
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