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A favorite of mine from a couple sessions ago... "I flip off the balcony."
I should mention that this player is notorious in my lodge for rarely rolling higher then a 5 for anything. Initiative, to-hit, skill checks, random "did I just see the boulder that hit my face" checks... He rolls 5 or less every time. Doesn't help that he took 7 in Int and Wisdom.
That session he face planted from a 2nd floor drop three different times, only one of them wasn't due to his intentional actions. One of the times he failed a DC 5 acrobatics check to jump off shack's roof safely. The quote was when he tried earlier in the session to awe the npc with his acrobatic greatness by preforming a Jackie Chan or Bruce Lee style flip from the 2nd floor balcony to the ground below. He rolled a 1.

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My first character i made was traveling with a bard a fighter and a cleric (all males except for my rogue). We were trying to secure passage on a boat and didn't have enough money so we were brainstorming ideas. After a minute of silence the bard all of a sudden said "[b]why dont we offer the ugly chick for a night.[/b)" the boat captain was blind

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My Daughter and I played several scenarios with another player whose character used a wooden stake as a weapon. The first, maybe, 4 scenarios, that player would only be able to threaten with his stake, or maybe wave it around, then in the 5th he finally did damage with it. Well my daughter had a revelation that he was actually waving around a stake, and said out loud that the last couple of sessions, she couldn't understand why anyone could be afraid of a piece of meat (steak).