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When you get your ideas from the Bards' Guild
(ttrpg.network)
This comic follows on from the Previous comic which might help provide context.
Technically any poker depicted in a comic strip qualifies for this.
Would she get advantage on the roll if she pointed out that practice under stressful but safe circumstances is both responsible and good preparation for unforseen stressful and potentially dangerous situations? So, really, playing strip poker is the mature and responsible course of action here.
as a DM, I normally give situational advantage to anyone who makes an argument that appeals to the values of the person to be convinced.