You can risk being uncool or you can risk being cruel. Only one of those follows you around.

Both options cost you something in the moment, which is why they get treated as an even trade. They are not even. Being uncool is temporary and almost entirely about how a handful of people see you this year. Cruelty lodges in somebody else and in your own memory, and it keeps turning up long after the room has forgotten the joke.

When the choice arrives, and it tends to arrive fast, take the uncool side by default. You can always decide later that you overcorrected; the other direction does not offer that option.