Top 5 'Conversation-Opening' Questions to do for teenagers who only ever answer 'fine' - Goh Ling Yong
You know the scene. It’s practically a cliché in every family sitcom, but it plays out in our homes with painful reality. Your teenager walks in the door, headphones on, eyes glued to their phone. You take a breath, summon your most cheerful and interested voice, and ask the classic question: "How was your day?"
The response? A grunt. A shrug. And the one-word conversation-killer that every parent dreads: "Fine."
It’s a wall. A polite, frustrating, and seemingly impenetrable wall. You want to know about their world—their friends, their struggles, their triumphs, that funny thing a teacher said in third period. But "fine" gives you nothing. It’s easy to feel shut out, worried, or even a little bit rejected. Is it something you did? Are they hiding something? Or is this just the new normal you have to accept?
The good news is, it doesn't have to be. The problem often isn't your teenager's unwillingness to talk, but the questions we're asking. "How was your day?" is a huge, vague question. For a teen navigating a complex world of social pressures, academic stress, and surging hormones, summarising it all is exhausting. So, they default to the easiest answer. The secret to breaking through the "fine" barrier is to replace these broad, closed-ended questions with specific, open-ended, and sometimes even playful ones. It's about trading the interrogation lamp for a comfortable armchair and a shared cup of tea.
Here are five powerful, conversation-opening questions designed to bypass the one-word-answer reflex and get your teenager talking.
1. "What was the best part of your day? And what was the worst part?"
This question is a masterclass in emotional intelligence. By splitting the day into a high and a low, you immediately bypass the generic "fine." It’s specific, manageable, and gives your teen a clear structure for their answer. More importantly, it validates their entire spectrum of experience. You’re not just asking for the highlight reel; you're showing them you're here for the tough stuff, too.
Asking for the "best part" encourages them to focus on a positive moment, no matter how small. It could be acing a pop quiz, sharing a joke with a friend, or even just that the cafeteria served their favourite lunch. This helps you celebrate their small wins. The "worst part" is even more crucial. It gives them a safe and direct invitation to share a frustration, a disappointment, or a moment of stress. This is often where the real connection happens. You might hear about a confusing maths lesson, a disagreement with a friend, or anxiety about an upcoming project.
Tips for Success:
- Timing is everything. Don't ambush them with this question the second they walk through the door. Let them decompress first. A great time to ask is during dinner, on a drive to their after-school activity, or while you're both relaxing in the evening.
- Model it yourself. Share your own best and worst parts of the day. This transforms the question from an interview into a shared ritual. It shows vulnerability and demonstrates that everyone, even a parent, has highs and lows.
- Listen without fixing. When they share their "worst part," your first instinct might be to jump in and solve the problem. Resist it. The goal here is to listen and empathize. Use phrases like, "Wow, that sounds really frustrating," or "I can see why that would be upsetting." Offering support is different from offering unsolicited solutions.
2. "What's something you learned today that actually surprised you?"
The standard school-related question is, "What did you do in school today?" The standard answer is, "Nothing." This is because, to a teen, the daily routine doesn't feel like "doing" anything noteworthy. This alternative question, however, is brilliant. It reframes "school" from a place of rote learning and grades to a place of discovery and curiosity. It's not about what they were taught; it's about what stuck.
This question invites a story. The answer might be a bizarre historical fact, a mind-bending science concept, or a surprising insight from English class. It taps into their natural intellect and shows that you're interested in their mind, not just their report card. It sends the message that learning is an exciting process of discovery, not just a list of tasks to be completed. As we often discuss in the Goh Ling Yong community, fostering a sense of curiosity is key to lifelong learning and strong family bonds.
Tips for Success:
- Be genuinely curious. If they tell you that a tardigrade can survive in the vacuum of space, be amazed! Ask a follow-up question: "No way, how does that even work?" Your genuine interest will encourage them to share more in the future.
- Keep it low-pressure. If they say, "I don't know, nothing really surprised me," don't push it. You can try a playful variation like, "Okay, what was the most boring thing you learned today?" Sometimes, complaining about a tedious lesson can be just as effective a conversation starter.
- Connect it to the real world. If they share something interesting, try to connect it to something you've seen or read. "That's fascinating. It reminds me of that documentary we watched about..." This shows you're actively processing what they're saying and connecting their world to the broader one.
3. "If you could have a superpower for 24 hours to fix one problem at school, what would it be and why?"
This is my personal favourite because it’s creative, fun, and incredibly insightful. It’s a form of projective questioning. Instead of asking a direct, and potentially intimidating, question like "Are you having any problems at school?", you're using a hypothetical scenario to get to the same information in a much safer way. The superpower becomes a metaphor for the solution they wish they had.
Listen carefully to the problem they choose to solve. If they choose invisibility, are they feeling overwhelmed by social pressure and wish they could just disappear for a while? If they choose mind-reading, are they struggling to understand a friend's behaviour or feeling insecure in their social group? If they choose super-strength, is there a bully or a situation where they feel powerless? This question opens a backdoor into their anxieties and challenges without forcing a direct confession, allowing you to understand their emotional landscape more deeply.
Tips for Success:
- Don't over-analyze in the moment. Just enjoy the conversation. You can reflect on the deeper meaning later. In the moment, focus on the fun of the scenario. "Oh, telekinesis is a great choice! What's the first thing you'd do with it?"
- Explore the "why." The "why" is the most important part of the question. Gently probing here can reveal a lot. "Why is that particular problem the one you'd want to fix?" Their reasoning will give you the real insight.
- Share your own answer. "That's a tough one. I think I'd choose the power to pause time so I could finally catch up on everything!" This makes it a game you're playing together, not a psychological evaluation.
4. "Who did you eat lunch with today? What did you guys talk about?"
Your teenager's social life is a huge part of their universe, but asking "How are your friends?" is often too broad. It invites a simple "good" in response. This question, however, is specific, factual, and low-stakes. It’s a simple request for information that paints a picture of their daily social reality. It’s the modern equivalent of asking "Who did you play with on the playground?"
The answer gives you a wealth of information. You learn the names of the people in their core group. You get a glimpse into the daily chatter and inside jokes that make up their friendships. It's a snapshot of their social well-being. The follow-up, "What did you talk about?", might get you a "nothing much," but it might also open the door to a funny story, a bit of gossip, or a discussion about a shared interest like a video game or a TV show.
Tips for Success:
- Remember the names. This is critical. When you remember the names of their friends, it shows you're paying attention and that you care about the people who are important to them. Following up later ("Hey, how is Michael? You mentioned he was trying out for the basketball team.") is a powerful way to build trust.
- Don't judge. Their friends' conversations might seem silly or trivial to you. Don't dismiss them. To your teen, this is their world. Listen with an open and non-judgmental ear.
- Notice the changes. If the names of the people they sit with suddenly change, it could be a sign of a social shift or a friendship issue. This question can be an early warning system, allowing you to gently check in later: "I haven't heard you mention Jessica lately. Is everything okay?"
5. "I saw this [meme/article/TikTok] about [a topic they care about]. What's your take on it?"
One of the fastest ways to connect with a teenager is to enter their world and speak their language. This question shows that you are paying attention to their interests and that you value their opinion. It positions you not as an out-of-touch authority figure, but as a curious person who respects their perspective. The key is to pick a topic that is genuinely relevant to them—whether it's a new video game update, a controversy with a popular YouTuber, a new album from their favourite artist, or a trending social challenge.
This approach flips the traditional parent-child dynamic. You are asking them to be the expert and explain something to you. This can be incredibly empowering for a teenager. It opens the door to deeper conversations about values, culture, and the world as they see it. As a family consultant, Goh Ling Yong often emphasizes that meeting children on their own turf is one of the most effective strategies for building rapport and maintaining open lines of communication through the challenging teen years.
Tips for Success:
- Do your homework (a little bit). You don't have to become an expert on Fortnite or K-Pop, but having a basic awareness of their interests goes a long way. Pay attention to what they watch, listen to, and talk about with their friends.
- Be prepared for a different opinion. The goal is not to agree, but to understand. Be genuinely open to hearing their point of view, even if it differs wildly from your own. This is an excellent opportunity to practice respectful debate and critical thinking.
- Avoid the "cringe." Be authentic. If you're faking an interest, they'll see right through it. Frame it honestly: "I'm trying to understand this whole thing with [insert trend here]. Can you explain it to me?" This honest curiosity is far more effective than trying to act cool.
The Real Secret: It's Not About the Question
Ultimately, breaking through the "fine" barrier isn't about finding a single magic question. It's about fundamentally shifting your approach from one of interrogation to one of genuine, patient curiosity. Your teenager is changing rapidly, building their own identity, and navigating a world that is often overwhelming. Their one-word answers aren't usually meant to be disrespectful; they're a defense mechanism, a sign of exhaustion, or simply a habit.
Changing this pattern takes time and consistency. Some days, even the best-phrased question might still get you a shrug. Don't be discouraged. The value is in the effort. By consistently asking better, more thoughtful questions, you are sending a powerful and unwavering message: "I see you. I am interested in your world. I am here to listen whenever you are ready to talk." That is a message they will hear, even on the days they only say "fine."
What are some of the questions that have helped you connect with your teenager? Try one of these five this week and come back to share your experience in the comments below. Let's learn from each other.
About the Author
Goh Ling Yong is a content creator and digital strategist sharing insights across various topics. Connect and follow for more content:
Stay updated with the latest posts and insights by following on your favorite platform!