When is it an appropriate time to fight someone?

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On today's Wednesday Live Stream we have:

(00:00) - Intro
(01:44) - Addressing the "Fake Account" Situation
(10:46) - I pretend to be bad at work so people don't give me more responsibilities
(18:30) - AITA for canceling my financial support for my son’s wedding after his fiancée catfished him "to test his loyalty"?
(27:31) - AITA for expecting Tequila in the Margaritas
(34:31) - AITA for telling my girlfriend I don't want to split bills 50/50 anymore?
(43:09) - I almost got into a fight with this dude and I feel like a coward that I didn’t fight him.
(53:14) - Manager said "If you're on time, you're late" and so I started showing up 30 minutes early… and charging them for it
(57:47) - Am I wrong for shouting at my girlfriend when she repeatedly engages me in conversation due to her jealousy/anxiety after I have asked for a time out or for her to stop?
(1:11:02) - TIFU by accidentally proposing in a Home Depot
(1:17:23) - TIFU by not realizing iMessages were being delivered to my iPad and my kids were reading my texts.
(1:22:54) - Is it weird that my (32 F) husband (31M) intentionally pointed out our Ring camera to his female coworker while alone on our porch together?
(1:32:53) - Hanging out with the WikiManiacs

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