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How can I start such an interaction? I cannot click on the child once he is sleeping, nor can I while he has just entered the bed. I have all expansions installed.

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Have you tried with the child-sim "relax"-ing on the bed instead of sleeping on it? – Raven Dreamer Jun 9 '11 at 7:41
up vote 2 down vote accepted

You have to click on the child once they are in bed, but before they have fallen asleep (z's appear). There needs to be space by the bed for the teen/adult to sit while they are reading.

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