Generate 100 Joyful Family Story Questions

You are an expert oral historian and interviewer. Your job is to design a warm, joyful conversation that helps me hear and enjoy the stories of someone I care about.

Create exactly 100 interview questions, grouped by theme. These questions should feel specific, playful, and story-triggering so the person being interviewed naturally smiles, laughs, or lights up as they remember. The goal is simple: spend meaningful time together, see the world through their eyes, and enjoy the memories that surface as they walk back through their life.

First, outline 5–8 themed sections that fit this person’s life and background. Examples: Early Home and Family, School and Mischief, First Jobs and Work Life, Love and Friendships, Holidays and Traditions, Everyday Quirks and Habits, Big Moments and Turning Points, Wisdom and Observations. Give each section a one sentence description.

Then write the questions:
Exactly 100 questions in total, grouped under the sections, clearly numbered.
Every question must be open ended and specific enough to suggest a scene, person, place, or situation.
Aim for questions that invite vivid detail and mini stories, for example:
“What’s the first house you lived in that you remember? What did you love about (or hate) about living there?”
“What’s the naughtiest thing you did that your parents never found out about?”
“What was your very first ‘job’ or ‘chore’ that you got paid for? What did you spend the money you earned on?”
“Who was the biggest character on your street, and what made them unforgettable?”
“Tell me about your wedding day (or the day I was born). Who was there? Did it go the way you thought it would be?”
Do not use vague prompts like “What was your childhood like?” or “Tell me about your life.”
Use simple, natural language in line with their age, culture, and personality.
Keep the tone light, warm, and enjoyable. Focus on everyday life, humour, character, and moments that fascinate us, not on illness, regret, or trauma unless I explicitly allow it.
Avoid therapy style questions like “How did that make you feel deep down?” and let feelings emerge through the story itself.

After the 100 questions, add:

2–3 friendly opening lines I can use to explain what we are doing. Emphasise fun, curiosity, and time together, for example: “We realised we have never heard half your best stories and thought it would be fun to sit and talk through some of them.” Do not mention “before it is too late” or time running out.

5–8 short follow up prompts I can use after any answer to deepen the story, for example: “What happened next?”, “Who else was there?”, “What little detail do you still remember clearly?”, “What would surprise us most about that time?”

3–7 simple tips to keep the conversation relaxed and natural, including low key ways to record (such as a phone on the table, short sessions, focusing on chatting rather than performing).

Structure your response in this order:
1. Themed section list with 1–2 sentence descriptions.
2. The 100 questions, grouped by section and numbered.
3. Opening lines.
4. Follow-up prompts.
5. Practical tips.

Use the details below to tailor themes, wording, and tone:
– Who I am interviewing (for example, “my dad,” “my grandmother,” “my partner’s parents”):
– Approximate age or generation:
– Where they grew up (city/country/type of place):
– Any specific topics to lean into (for example, school years, raising kids, immigration, work life, their parents and grandparents):
– Any specific areas that should be avoided: