Raise a Glass to the Messy, Cringey Wedding Toast

The Art of the Wedding Toast: Balancing Humor and Heartfelt Moments

A prevalent style for best man or maid of honor speeches involves a gentle roast. Typically, the best man draws upon personal stories to playfully tease the groom he knows well, while offering generalized compliments to the bride.

The Gentle Roast: A Popular Toasting Style

The aim is to evoke mild embarrassment from the groom, but within limits. Critically, the humor should not be understated. This balance is essential not only for enhancing the speech’s dramatic impact, but also because effective teasing builds anticipation for the subsequent shift to sincerity. A roast lends credibility to more sentimental expressions that follow.

Humor as a Foundation for Emotional Connection

Humor, humor, then sentimentality – this represents the classic framework of a wedding toast. While comedy is often said to be more challenging than tragedy, achieving genuine sentiment in a toast is equally complex. The crucial understanding is the intrinsic connection between these two elements.

Insights from a Comedy Writer: Using Humor to Evoke Emotion

This concept was recently highlighted by Simon Rich, the writer behind the Broadway production “All In” and contributor to the film “Inside Out.” In a recent interview, when asked about Pixar’s techniques for making audiences cry, Rich shared, “While I prefer not to reveal specific techniques, the primary approach is to initially disarm the audience, ideally through comedy.” He elaborated, “Surprise is key. You need to gently lead them into a state of emotional ease.”

Embracing Imperfection: It’s Okay to Bomb

The most impactful toasts, like the most compelling art, defy convention. And the funniest speeches often contain an element of truth. Perhaps the most difficult aspect to accept is the possibility of failure. Comedians experience bombing routinely, as do artists and writers. It is rarely as catastrophic as anticipated. Indeed, even in bombing, there are benefits, notably, the creation of memorable moments surpassing even successful attempts.

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The Honesty of Imperfect Toasts

In her 2017 book, “Wedding Toasts I’ll Never Give,” Ada Calhoun, an author who has explored themes of love, marriage, and divorce, offers an understanding perspective on disastrous wedding toasts.

“Perhaps,” she conveyed via email, “messy toasts resonate because we recognize that relationships often veer off course. Love and marriage are inherently complex. Therefore, toasts that acknowledge this inherent messiness, whether in their delivery or content, are not only more entertaining but also more authentic.”


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