It’s partly why the most popular brand of best man or maid of honor toast is the gentle roast. The best man leans on personal stories to insult and haze the groom he knows well, then gushes vaguely about the bride he doesn’t.
The goal here is making the target cringe, but not too much. But — and here is where I make my stand — not too little. That’s not just because a speech benefits from drama. It’s also that the more you tease, the more likely you are to get a laugh. Roasting gives you credibility when you pivot to a more emotional sentiment.
Funny, funny, schmaltz. That’s the classic structure of a wedding toast. People always say that comedy is harder than tragedy, but with toasts, the schmaltz is just as tough to get right. The key is to understand that the two are inextricably linked.
I recently learned that from Simon Rich, the writer behind the Broadway hit “All In,” who also worked on the movie “Inside Out.” When I asked in a recent interview what he learned at Pixar about how to get audiences to cry, he told me, “I don’t want to give away tricks, but the biggest one is to disarm them, ideally with comedy.” He continued: “You need to get them by surprise. You need to lull them into a kind of emotional complacency.”
The best toasts, like the best art, break convention. And the funniest ones say something true. The hardest idea to accept? It’s OK to bomb. Comedians do it constantly. So do artists and writers. It’s never as bad as you think it will be. But among the benefits of bombing — and there are some — is this one: It produces more memories than most versions of success.
In her 2017 book “Wedding Toasts I’ll Never Give,” Ada Calhoun, a good friend who has written about love, marriage and most recently divorce, offers kind words about the train wrecks of bad toasts.
“Maybe messy toasts feel good because we know that relationships often go off the rails too,” she wrote over email. “Love is messy and marriages are messy. Toasts that, in form or content, nod to that are not only more entertaining: They’re also more honest.”
