A non-automated version of this existed for a time: EA Pen Pals. I used it a couple of times and enjoyed it. Might be worth talking to the people behind that project to learn about their experiences.
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Less Wrong (text)
Less Wrong (link)
A non-automated version of this existed for a time: EA Pen Pals. I used it a couple of times and enjoyed it. Might be worth talking to the people behind that project to learn about their experiences.