The well-done toast warms a whole room. Stumbled through, or delivered as droning dissertation, it becomes an unfortunate bit of family lore. Here, some success tips from toastmasters.
Credit: Illustration: Edwin Fotheringham

My father gave the best toast I have ever heard. It was at my brother's wedding in 1986. On that June day, one of the least talkative men I've ever known stood up and delivered a completely unscripted speech that was riveting, funny, and poignant. He stood, smiling and poised, entertaining an audience of more than 200. And I sat, stunned, at his perfect tribute. Later I asked my dad, "Who was that up there? How did you do it?" He smiled and answered as if he had been toasting people in perfect fashion for his entire life: "You just have to have the right thing in your heart." Turns out my dad was intuitively right about something that causes most of us to break out in a cold sweat: the heartfelt public tribute at a holiday dinner or special occasion. Toasting someone you love can become a great pleasure if you follow a few simple rules, gleaned here from a diverse range of experts. These rules are worth heeding because, as Martha Stewart Weddings' editorial director, Darcy Miller, so perfectly puts it, "There's nothing more awkward than sitting in a room where everyone is thinking, 'Oh my God, stop now!'"

1| The same way you get to carnegie hall: practice

"A good toast does not consist of walking into a room, having a bunch to drink, and then, when you're brave, standing up and going, 'OK, I want to make a toast.'"

—Pat Johnson, Toastmasters International President

Everyone agrees on one point: Preparation separates the doomed from the eloquent. "It's an interesting thing," says Johnson. "I've never seen a toast that was kind of OK. They're either absolutely disastrous, or they're prepared." She suggests the obvious idea of writing your thoughts down to help you focus and organize. Then the crucial bridge: "You really have to work to put it into your speaking voice, because we all have two voices—the written and the spoken—and the toast definitely has to be in your speaking voice."

Johnson's belief is that as you speak the toast a few times, in front of a mirror or a thoughtful (and preferably brutally honest) test listener, you begin to internalize. "When we internalize, something magical happens. We no longer have to read, and we start to speak from our hearts and say what we think and feel." Rehearsing gives you time to get comfortable with what you're saying, freeing you to connect with the audience when the time comes and make eye contact with the people or person you're honoring. This plants you firmly in the moment and brings you closer to your own emotions, hopefully allowing them to shine through your words and your anxiety.

2| Consider the audience

"I always just steel myself when the best man clinks his glass. It sounds sort of like the rumbling of the guillotine into place."

—Calvin Trillin, journalist, The New Yorker contributor, The Nation verse columnist

Preparation is crucial and gives you time to think about the people you're addressing—from children to in-laws to grandparents—and to make sure what you're saying is common knowledge among those people. A toast should not spend time teaching people long, complicated things about the person being toasted; this is a celebration of things already known and loved. Inside jokes are taboo and, unless it's a stag party, off-color humor is out.

The price of not considering the audience is dreadfully high. "I suppose if you collected the most embarrassing public speeches from America every year, about half of them would be the best man's toast at the rehearsal dinner," says Trillin. "He's trying to sort of tease the groom but actually just manages to mortify the bride or somebody's mother or his own wife."

3| Short, and to the subject be true

"Brevity is a virtue. ... If you can hit the long ball, do it. If you can't, hit your single and get offstage."

—Dan Okrent, author, former editor, and off-Broadway producer of Old Jews Telling Jokes

Overstaying your welcome is another mistake you can avoid if you rehearse and time yourself. Johnson says two to three minutes is an ideal length. "The good toasts are organized," says Trillin. "They do what people at The New Yorker used to call 'close the circle.' They say something, and they get around to it at the end again. And they tend to be short. I don't think anybody ever gave a very long toast that was appreciated."

There are exceptions: "Nothing beats a good story," says Okrent, as he recalls a long toast given by the late writer George Plimpton. "Plimpton went on for 12 minutes, but it was George Plimpton. It was brilliant and nobody wanted it to end." Unless you're in Plimpton's league, edit your toast.

"A lot of people think the toast is supposed to be the Gettysburg Address," says Larry Meyers, father of comedians Seth (Saturday Night Live) and Josh (MADtv). "Something so profound that everyone is going to walk away and never forget. But truth is, everybody forgets almost everything. Make it short and, if you can, entertaining. Let the content show your affection. People forget that the toast is about the people they're toasting. They end up talking about themselves, and it tends to be sappy and long."

4| You gotta mean it

"Any toast that evokes some kind of emotion is right on, whether it's a laugh or a tear or a lump in our throats. If you can get all that in two or three minutes, I would say it's an amazing toast."

—Pat Johnson

Everyone likes humor, but we're not all funny. Especially in tight clothing and high-pressure situations. It is, in fact, the long reach for humor by the person with short arms that causes the most discomfort. Even people who are consistently funny can't always pull that off in a toast. The overriding rule is to be genuine.

"I can always get a laugh, but I can't always convince people of my sincerity," says Okrent. "So the way you do that is forget about the laugh and just go for the sincerity. For me this happened at my wife's 60th birthday party. My dear, dear friends know that I'm basically a clown, but I decided not to clown it and to look deeply into her eyes and tell everybody what I thought about her. She said it was the best toast ever."

5| Keep it personal

"I think the most important thing is deep familiarity with the person you're toasting. My failures as a toaster have always been for people I didn't know well enough, and I'll never do that again."

—Dan Okrent

Search for words and stories that have deep meaning for you, and speak to your connection with the person being toasted. Okrent explains that to him, a great toast includes something anecdotal. "It helped that I was toasting the woman I've been married to for 34 years. That's familiarity."

As kids, Darcy Miller and her sister made up lyrics and performed songs at their parents' dinner parties, so at her wedding, Darcy's sister prepared tailored lyrics to "You'll Be in My Heart." Another spot-on toast at Miller's wedding was given by her boss of almost 20 years, Martha Stewart, who fixed Miller up with her husband, Andy Nussbaum. Everyone who knew Andy knew the goofy fact that in fourth grade he learned all the prepositions in alphabetical order and to this day recites them. Stewart's toast included all the prepositions in alphabetical order. "I can't tell someone what's personal to them," says Miller. "You need to think about that and be yourself, let the toast reflect who you are. The best toasts come from the heart."