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Your day. It's simple, and that's what it breaks down to in the end. If you start by asking him what he did today, even if he gives a simple answer, he'll at least ask you what you did, and that will open you up to tell him. Give him some details, but not a lot and hopefully something that one of you says will spark something that the other one is thinking about. Never ever ask what he's thinking about though, its a wast of time, and he'll always say either "nothing" or some variation of that, and he'll get annoyed at you.
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