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I've been reading about all the problems people are having on the official site and someone said they have to make sure their singer is in their work clothes, otherwise they can't do the sing a grams. Maybe try getting her to change into that outfit before attempting them.
have you checked if the sim you're delivering to isn't in a rabbithole? sometimes the game gives you the opportunity to deliver a sing-a-gram while the sim is outside but then he enters a rabbithole.