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Is it permissible for a man to be at a woman's home at night if both of her parents are at home, but sleeping? What if they are awake?

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see here: sie.org/library/article_cdo/aid/2312231/jewish/… -- check out the footnotes as well --- it's not an exact answer, since it only discusses if one of the parents are there, not if both are. I didn't look up the footnotes, so I don't know if they discuss it there. –  Menachem Jan 26 at 6:04

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They would have to be in the same room as either the man or woman. In the same house is not enough, since a closed door is effectively a different place. Since you can not see into it from outside. While sleeping only works if the person is easily roused - a deep sleeper is not an effective shomer. And in a different room is certainly not enough while sleeping, even if it may be OK if the person is awake and you expect they might enter unannounced.

A shomer is not a "game" - the person must actually guard, so anything that prevents that (loud noise, closed door, deep sleeper, etc) negates what they do.

This is on top of all the restrictions in what Menachem linked to.

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Citations to sources would vastly increase the value of your answer. –  msh210 May 13 '12 at 8:28
Who says a Shomer is not a "game"? Baalah BaIr "could be" –  Shmuel Brin Feb 19 at 4:15

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