In a HU match when is it acceptable to request a reload?

[Ship Ship McGipp]

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meh I am prolly -EV with short stacks so I have no problem asking them to reload at any time.

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man this is so true, sometimes when they get to 25 bbs i'm just giving them the next 25 so they can play with at least 50, but they're too bad to leave and i need to drag them on incase they go nuts to rebuy 100 or w.e