Don't write your wedding toast (do this first)

Today's Tip: Writing A Wedding Toast That Doesn't Make People Wince

A father-of-the-bride toast people remember takes about 20 minutes to write. But you don't start by writing.

Let me explain…

My friend Warren has been dreading Saturday for three weeks. His daughter Kate is getting married in Boise, and he agreed months ago to give the father-of-the-bride toast — before he understood what that would cost him.

Warren is 67. He spent 42 years running a locksmith shop with his brother, and he's given plenty of small speeches over the years… birthdays, retirement parties, a eulogy for his mother he still remembers word for word. But this one has him stuck. He's filled six pages of a yellow legal pad. Every version starts with "Ladies and gentlemen…" and dies by the third sentence.

Sound familiar? Whether it's a wedding, a retirement party, a 50th anniversary, or a milestone birthday, the assignment is the same. Get up in front of the people who know you best, say something honest, and don't embarrass yourself.

Last Tuesday night, Warren opened Claude on his phone — the free version at claude.ai, no account fuss, just typed straight into the browser. He didn't ask it to write the toast. He asked it to interview him.

Twenty minutes later he had four specific memories, three concrete details he'd forgotten about Kate, and the opening line. Not from Claude. From himself. Claude just knew what questions to ask.

Here's the prompt that does the interview…

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★ Copy-Paste Prompt

Works in Claude, Gemini & Grok

I need to give a wedding toast for my daughter Kate at her wedding on Saturday. I am the father of the bride. The wedding will have about 90 guests, including her fiancé's family who I've only met twice. My toast should be about 3 minutes long.

I am NOT a writer. Do NOT write a draft yet. First, interview me. Ask me questions one at a time until you have all five of these:

1. One specific memory of Kate as a child — something small, not a milestone — that tells you who she is

2. One thing she has taught me as an adult

3. One thing I've learned about her fiancé that surprised me

4. One moment where I saw the two of them together and thought "yes, this is right"

5. What I actually hope for them, in plain words no greeting card would use

Wait for my answer to each question before asking the next. Do not add commentary between questions.

After I've answered all five, draft the toast. It must:

- Be under 400 words
- Sound like a 67-year-old father, not a Hallmark card
- Never begin with "Ladies and gentlemen" or a dictionary definition
- Not include any joke I did not tell you
- End with the specific words I want to say to Kate and Marcus, not a generic well-wish

Then flag every sentence I might trip over emotionally, so I can practice those in advance.

Why this works: The trick is the interview. Ask Claude to write a wedding toast cold and you'll get exactly what you're afraid of — generic, warm, forgettable. Ask Claude to interview you first, and the memories that make a toast worth listening to come out of your own head, in your own voice. Claude just does the harder work of pulling them out.

Warren answered the questions in his kitchen with a cup of coffee getting cold. Kate at age six, refusing to let him tie her shoes even though the loops were uneven. Kate at 34, telling him it was okay to slow down after his brother passed. Marcus, her fiancé, quietly fixing the porch railing on Thanksgiving without being asked.

None of those had made it onto the legal pad. All three made it into the toast.

By the end of the session, Warren had a 380-word draft that sounded like him — because it WAS him. Every specific detail came from his own memory. Claude organized the pieces, cut the parts that dragged, and flagged the two sentences about Kate's mother he'd need to practice out loud so he could get through them Saturday.

★ Today's "Aha!" Moment

You are not the writer of your wedding toast. You are the source material. Claude is the interviewer.

I know what you're thinking… doesn't using AI for something like this make it fake? Isn't the whole point that it comes from the heart?

The heart part is exactly what doesn't change… the memories are yours. The details are yours. The words your daughter or son remembers 20 years from now are words you would have said anyway — if you'd known how to get them onto the page. Claude is the interviewer, not the ghostwriter. Give the same prompt to your neighbor and you'll get a completely different toast, because the source material is different. That's not fake. That's just editing.

★ One Thing to Watch

Do NOT skip the interview step. If you paste "write a father-of-the-bride toast for my daughter Kate" and hit enter, Claude will hand you exactly the generic, cliché-heavy speech you were afraid of. The whole method depends on making Claude ask the questions first. Every specific memory you type in becomes fuel for the toast. Every question you skip becomes a hole the AI fills with a Hallmark card.

The wedding is Saturday. Warren has 20 more minutes of work to do — practicing the ending out loud with his wife Diane until he can get through it without stopping.

Whatever you're speaking at this summer — a wedding, a retirement party, a milestone birthday, a memorial service — the 20 minutes are the same. Start with the questions, not the page.

★ ★ ★

Tool Spotlight ★

Claude

Site: claude.ai

Made by: Anthropic

Cost: Free tier available

Claude is the careful writer of the three main AI tools — and for anything with emotional weight, that carefulness is exactly what you want. Where Grok reaches for clever and Gemini reaches for facts, Claude tends toward honest. That's why it lands so well for letters, toasts, condolence notes, and any writing where the wrong word ruins everything.

The free version at claude.ai now runs Claude Sonnet 5, which became the default for free accounts on July 1st of this year. It's the same model that used to sit behind the paid wall. You can upload photos and documents, save projects for topics you return to often, and search the web from inside the chat. For someone using AI for a specific writing task and then closing the tab, the free tier is more than enough.

Best for: writing letters, drafting speeches, editing what you already wrote, summarizing long documents, and explaining anything complex without talking down to you.

★ ★ ★

★ Quick Wins

"Read it back to me flat" — After any AI drafts something you plan to say out loud, paste it back and type: "Read this to me as flat monotone text. Where would I run out of breath in one sentence? Which sentences would be hard to say without choking up?" Claude will mark the trip hazards so you can practice those parts before the microphone finds you. Works especially well in Claude and Gemini; Grok is fine too.

The two-generation joke test — Family joke you're worried about? Paste it in and type: "Explain this joke to a 12-year-old and to an 82-year-old. If they'd both smile, tell me to keep it. If either would blink politely, tell me to cut it." Saves you from the awkward silence at the reception. Works in Claude, Gemini, and Grok — Claude gives the most honest read.

The 60-second milestone note — When a friend hits a big anniversary, retirement, or birthday and you owe them more than "Congrats!", type: "Write a two-sentence note to send [NAME] for their 40th wedding anniversary. Warm but not sappy. End with a specific memory of them from years ago, not a generic well-wish." Give it one real memory and you'll get back something worth reading. Works in Claude, Gemini, and Grok.

Skill Builder: The Anti-Cliché Prompt

The biggest tell that AI wrote something is not any single mistake. It's a set of predictable phrases that show up over and over again — "nestled in," "testament to," "beautiful journey," "each and every one of you," "unwavering support." Once you notice them, you can't unnotice them.

That's the trouble with using AI for anything personal. The words are technically correct. But collectively they make the writing sound like a card someone left in a hotel drawer. And the harder AI tries to sound warm, the more it reaches for those exact phrases.

The fix is simple. Give the AI a list of phrases it can't use. Bans are more powerful than instructions. If you tell AI to "write naturally," you're giving it nothing to grip. If you tell it "never say 'testament to' or 'unwavering,'" you're removing the crutches it reaches for by default. What comes back sounds noticeably closer to how a person actually talks.

Save this prompt. Paste it before anything you write that has to sound like a person wrote it.

★ The Anti-Cliché Filter

Works in Claude, Gemini & Grok

I'm about to give you a draft to rewrite. Before you respond, promise not to use ANY of these words or phrases anywhere in your reply:

"nestled," "testament to," "beautiful journey," "in the modern era," "at its core," "each and every," "unwavering," "unforgettable," "delve into," "streamlined," "elevate," "embark on," "in the realm of," "when it comes to," "a reminder that," "not just about," "more than just," "boasts," "vibrant," "rich tapestry," "meticulously crafted."

Also, no em-dashes. No sentences that begin with "In a world where…" or "As we…". No listicle openings.

If your rewrite would need any of these, find different words. If a sentence resists rewriting, tell me and suggest what to cut instead.

Here is the draft:

[PASTE YOUR DRAFT HERE]

Why this works: Once the tells are gone, your editor's ear turns back on. It's the AI clichés that made bad AI writing invisible to you in the first place. Ban them and you can hear the writing again — including the parts that still need work.

Try the ban list on your next email, your next thank-you card, your next draft toast. Read what comes back out loud. It won't be perfect… but it also won't sound like a chatbot pretending to be sincere.

Save the prompt somewhere you can find it. Every writer, even the ones with 40 years of practice, has a set of favorite phrases that show up whether they want them to or not. The ban list works on your habits too.

Don't write your wedding toast (do this first)

Backed By Elon Musk, This Could be the Next Hot IPO

It’s growing faster than Tesla and SpaceX

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