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I think it's gotten overused. I've seen it on shows and girls have told me guys used it on dates.
Maybe too it's how you're introducing it. Like if the date and conversation is flowing and you bring it up its just a small thing. If you're struggling for conversation and the date is spiraling downward and you bring it up.. It could appear you want to ask questions to make conversation.
I know routines have gotten a bad rap, but I kinda like the question game. It's just another little tool in your toolbox is all. Like you said, if it's a last ditch effort, then it may not go down the road you'd like it too. I wouldn't push away people from using it though.
Like with all things OP, adapt to the times. You could probably inject the question game without actually saying "hey lets play the question game", you can just throw in the questions in there while you're having a fun flirty conversation. Women don't know how they get picked up when they are in the moment. "It just happened" .