Saying “I’m proud of you” to a friend, face to face, feels weirdly risky. Say it. They’ll replay it for years.

Sincerity is riskier among friends than an insult, because the ordinary register is jokes and stepping out of it leaves you standing there with nothing ironic to hide behind. That is why it feels so strange to say something warm and completely straight to somebody’s face. It also explains the effect. People hold on to sentences like that for years and take them out again on bad days.

Say it to one person, in person, with no joke attached and no follow-up to soften it. Then let the pause be awkward.