Nostalgia Trip

What was the first album or CD you ever bought with your own money?

What was your go-to outfit when you were ten years old?

What’s a cartoon you could still watch and enjoy today?

What was the first 'grown-up' movie you remember seeing?

What was your favorite playground game or recess activity?

What is a smell that instantly reminds you of your grandparents' house?

What was the most 'rebellious' thing you did as a kid (even if it was small)?

Who was your first 'celebrity crush'?

What’s a movie from your childhood that you’re afraid to rewatch because it might be bad?

What was a fashion trend you followed that you now find deeply embarrassing?

What’s a song that was playing during a significant moment in your life?

Who was the first teacher who made you feel like you were actually good at something?

What was the 'coolest' thing you owned as a teenager?

What is a childhood tradition you’ve accidentally (or intentionally) kept as an adult?

What was the biggest 'drama' in your friend group during middle school?

What did you want to be when you grew up, and how close is that to your life now?

What’s a memory from your childhood that feels like a scene from a movie?

What was your favorite family vacation, and what made it so special?

If you could spend one hour in your teenage bedroom exactly as it was, what’s the first thing you’d touch?

What is a smell or sound that feels like a time machine to a specific year?

What is a lesson you learned as a child that you’ve had to 'unlearn' as an adult?

Which childhood friend do you wish you could talk to one more time?

What part of your 'younger self' do you miss the most?

What was a moment when you realized for the first time that your parents weren't perfect?

What is a fear you had as a kid that actually shaped who you are today?

If you could go back and tell your 13-year-old self one thing about their future, what would it be?

What’s a family story that gets told at every gathering, and how has it changed over time?