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"The best thing about how you play Monopoly is that you let the kids win."
The reason to mention this—oh so casually—is not so much about the particular board game as it is about the dark, insidious spider web of associations that goes along with it. For example, let's say your spouse's father was a business tycoon who mocked his young son for not being tough enough, and forced him to play rounds of impossible-to-win, ego-shriveling chess. Naturally, your spouse is terrified of growing up to be just like his dad. To help him with this daily horror, you can always say, "You're not like your dad," over and over, but the repetition will dull the point. Furthermore, in my wee experience, saying it so overtly will mean that he will never believe you. Insecurities are like this: they resist the truest, easiest solution to their madness. A roundabout affirmation that he is not the person he least wants to be, on the other hand, will make him think, "I'm not like my dad!" And as all of us know too well, we humans tend to believe that voice in our heads above all other voices. Bonus point: He may also let you win...