Winsome is not a bad word. But like any virtue, we can unwisely corrupt winsomeness into a dangerous vice. Untethered winsomeness can be sinful. It’s like the virtue of being gentle. It’s good to be gentle, but in some cases it would be sinful to be gentle. It’s good to be gentle as a general character trait, but it would be sinful to be gentle to a pit bull while it is attacking your daughter. The right virtue in that instance would be valor—courage in the face of danger to forcefully neutralize a lethal threat….
Winsomeness is sinful when you shift from winning some in a God-honoring way to selfish people-pleasing. There’s a difference between loving your neighbor according to the standard of God’s word and making your neighbor feel loved. That’s a shift from the objective to the subjective—from truth to feelings. Winsomeness is sinful when you try to win the approval of certain people the wrong way.
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