Life experiences and milestones give students a lot to talk about, whether they’re reflecting on their own past or imagining what’s still ahead. These questions work well for practicing storytelling, comparisons, and expressing emotions.
Questions are organized by level from beginner to advanced. A printable PDF of all the questions is available at the bottom of the page.
Beginner (A1-A2)
- Have you ever learned something new that surprised you? What was it?
- What are the three best memories from your childhood?
- What was your favorite birthday? How did you celebrate?
- What is a food you tried for the first time and loved? Where did you try it?
- What is the most beautiful place you have ever visited? What did it look like?
- What was the first job you ever had? What was it like?
- Have you ever won a prize or an award? Tell me about it.
- Have you ever been in the right place at the right time, where something lucky happened? What was it?
- Have you ever gotten lost somewhere? What happened?
- Have you ever met someone famous? Tell me about it.
- What is the longest trip you have ever taken? Where did you go?
- Have you ever moved to a new city or town? Was it exciting or scary?
Elementary (A2)
- What is the most exciting trip or adventure you have ever been on? What made it so exciting?
- Who was your favorite teacher growing up? What did you like about them?
- What was the scariest thing that ever happened to you? What makes it so scary when you think about it now?
- What is the best advice someone has ever given you about a big life decision? Why was it so helpful?
- Have you ever tried something for the first time and loved it right away? What was it, and why did you love it?
- What did you want to be when you were a child? Why did you want that job?
- Have you ever failed at something important to you? How did it go after that?
- What is the most difficult decision you have ever made? Why was it so hard?
- What do you remember about your first day at school? Why does that memory stick with you?
- What is the best gift anyone has ever given you? Why was it so meaningful?
- Have you ever tried a sport or hobby and then quit? Why did you stop?
Intermediate (B1)
- Do you think it is better to take a big risk and possibly fail, or to take the safer path in life? Why or why not?
- Should people be expected to reach certain milestones, like getting married or owning a home, by a certain age? Why or why not?
- If you could go back and change one major decision in your life, what would it be? What would you do differently, and why?
- In your culture, are there certain life experiences, like losing a job or getting divorced, that people avoid talking about? Why do you think those topics are so private?
- Should young people take a year off before starting university? Why or why not?
- If you could relive one day from your past exactly as it happened, which day would you choose? What was so great about it?
- Some people say that traveling is the best education. Do you agree? Why or why not?
- What is the bravest thing you have ever done? Would you do it again? Why or why not?
- Do you think people learn more from good experiences or bad experiences? Why do you think so?
- If you could give one piece of advice to your younger self, what would it be? Why that advice?
- Is it important to celebrate milestones like graduations or promotions, or are they just dates on a calendar? Why or why not?
Upper-Intermediate (B2)
- What do you think makes some people able to bounce back quickly after a setback, while others struggle for a long time? What are the biggest factors?
- How does a person’s cultural background shape which experiences they think of as important milestones, and which ones they might not even consider? Can you give me some examples from different cultures you know about?
- What are the advantages and disadvantages of going through a major life change, like a divorce, career shift, or moving abroad, when you are older versus when you are younger?
- How do difficult life experiences, like illness, loss, or failure, affect a person’s values and priorities in the long run? How much have your own experiences shaped what you value?
- How is the experience of making a major mistake different from the experience of missing an opportunity? Which one do you think is harder to live with, and why?
- How do shared experiences, like surviving a natural disaster, studying abroad together, or going through a difficult project, affect the bonds people form? How has something like this played out in your own life?
- How has social media changed the way people experience major life events like graduations, weddings, or having a baby? What do you think about those changes?
- Some people plan their lives carefully, and others prefer to go with the flow. What are the benefits and risks of each approach?
- What role does luck play in a person’s life compared to hard work and preparation? How have you seen this play out in real life?
- How do major life events like losing a job or going through a breakup sometimes lead to unexpected positive outcomes? Can you think of any examples?
- Some people say you should never compare your life to someone else’s. Is that realistic, or is comparison just part of human nature? What can be done about it?
- Many people say their school years were the best time of their life, but others disagree. What shapes whether someone looks back on a period of life positively or negatively?
- Some of the most successful people dropped out of school or failed many times before succeeding. How do these stories influence the way society thinks about education and risk-taking?
- People often say that difficult experiences ‘build character.’ Is this always true, or can hardship also damage a person in ways that don’t get talked about enough?
Advanced (C1)
- How does the pressure to achieve visible milestones (degree, marriage, career, children) affect the choices people make, even when those milestones don’t match what they actually want?
- Why do people from very different cultures seem to mark the same kinds of transitions (birth, adulthood, marriage, death, etc.) with rituals and ceremonies? What does that tell us about what it means to be human?
- When someone tells the story of a painful experience from their past, they often present themselves as either a victim or a survivor: two very different interpretations of the same event. What determines which story someone tells, and does it matter?
- Is there a difference between learning from an experience and simply getting used to it? How can you tell which one has happened?
- How does growing up during a particular historical moment, such as a war, an economic crisis, or a technological revolution, permanently shape the way a generation thinks about risk, trust, and opportunity?
- As people get older, they often say they wish they had worried less when they were younger. Why is it so hard to apply that kind of wisdom when you are actually living through a stressful time?
- People often keep the same friends from childhood or school, but rarely stay close to people they meet later in life. Why do early shared experiences create stronger bonds than ones that happen when we are older?
- In many countries, the milestones that defined a successful life 50 years ago (a stable career, homeownership, marriage by 30, etc.) are now out of reach for many young people. How does this gap between expectations and reality affect the way a generation sees itself?
- Some people say their biggest life-changing moments were things they did not choose such as an accident, a chance meeting, or an unexpected job offer. If the most important experiences in life are unplanned, what does that say about how much control we actually have over who we become?
- Parents often want their children to have a better life than they had, but they also want their children to appreciate what they have. How do these two goals conflict with each other in practice?