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The only type of "weird" captions that have us [scratching head] are the ones that come completely from out of left field and seem to have no correlation whatsoever to the screen capture they're supposedly captioning.
To protect the guilty, I won't cite an example - but I'm sure the regular readers of this board certainly know the type I'm referring to.
I've been giving serious thought to possibly celebrating the first anniversary of the Caption This! board in January by having a poll to pick the best caption of the past year. However, the list of nominees would probably be picked by the admin/mods (with the winner then voted on by the forum's members), so anyone who might like us to consider one of their captions for the poll might want to stay on our good sides.