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Boredom has an important function, because pushing through it can unleash creativity.
When you are wondering whether to say something negative about someone - even if it is true - the best rule to follow is, "I'll think about doing this tomorrow."
We human beings are definitely capable of loving more than one person, but it seems to go more smoothly if we don't love more than one person at a time.
You should not be hovering in the background, inflating the drama. Simply envelop him in love and affection and let him know that you will support his efforts, whatever they are.