Whenever you think that this is as good as it gets with the person -- they couldn't ever know you better or like you more. That's the best time. And do it fast before they start to forget you or you do some **** that pisses them off.
As early as humanly possible, and as proximate to the experience as humanly possible. If the time of our interaction was short, then you want to ask before our memory of the experience fades. Many of the people writing your letters are inhumanly busy, and LoRs are a low but recognized priority. Giving a wide time window makes us appreciate you more. But give hard deadlines so we have something to put in our planner.
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