Being a teenager can be tough. Whether your teen is navigating social pressures, academic stress, or just trying to fit in, adolescence is often a rollercoaster. As adults, we may laugh at our most awkward memories, but there’s a good chance you still remember a particular moment from those years that still makes you cringe. For me, it was the period from 8th grade through sophomore year. I was a moody, blue-haired teen, trying SO hard to fit in while also standing out. For many years, I felt a lingering sense of secondhand embarrassment for that version of myself.
The older I get, however, the more I feel a sense of compassion for that younger version of me– trying on different identities, desperately seeking approval (while pretending not to care), and trying to understand my place in the world. Whether your teen is struggling with social anxiety, trying to meet academic expectations, or simply navigating the pressure to belong, adolescence is a uniquely challenging time.
Like many teens, I mastered the art of one-word answers that deflected adults’ questions. ‘Fine,’ ‘Okay,’ and ‘Whatever’ were my go-to responses, like tools in a Swiss army knife—quick, convenient, and easily deployed to shut down any well-meaning question. Of course, this deflection was a defense mechanism. It was easier to say school was ‘fine’ than to admit I hadn’t turned in my math homework in two weeks. ‘Fine’ felt safe, even if it wasn’t the truth.
Now, I wonder: What would it have taken for me to open up? What did I need to hear? And most importantly, how can parents communicate with their teens in a way that fosters trust and security, making it easier for them to be open and honest? In this short blog post, I’ll share some insights I’ve gained from spending countless hours talking to teenagers about school.
Ask open-ended questions about your teen’s perspective.
Questions exist on a broad spectrum, from binary ones like “Did you have a good day at school?” to open-ended ones like “What do you think of your science class so far?” While binary questions can be helpful, they’re also the easiest for teens to deflect, especially when they’re feeling overwhelmed or unsure. A simple ‘yes’ or ‘no’ becomes a convenient shield. On the other hand, open-ended questions invite your teen to share more and help you get a glimpse into their thoughts.
When talking to your teen, try using questions that leave room for a wide range of responses. Questions that begin with how, why, or what tend to invite deeper answers, while prompts like ‘What do you think about…?’ help you better understand their perspective on a given topic. Avoid prying if you sense your teen is on the verge of sharing something important. A gentle follow-up like “Can you say a little more about that?” can encourage them, but often they just need time. Sharing their feelings may come in stages.
Teens often hesitate to open up because they fear judgment or criticism, or they may struggle to articulate their emotions. Keeping the conversation open and non-pressured fosters a sense of safety, which is key to moving beyond the typical ‘Fine.’
Travel in the same direction.
Conversations about school, grades, or plans can often become unintentionally confrontational. What starts as a casual chat can quickly turn tense. If you’re used to having these discussions while sitting across from your teen, try broaching sensitive topics when you’re side-by-side—perhaps while walking the dog or driving together. This physical alignment feels less oppositional and more collaborative. While your teen needs to be able to look you in the eye and share their feelings, sometimes it feels safer to open up when you don’t have to look directly at one another and are both looking ahead. The natural rhythm of walking can be calming, and awkward silences feel less uncomfortable.
By physically moving in the same direction, you subtly shift the energy of the conversation from conflict to collaboration. This simple adjustment can make it easier for teens to express their feelings without the pressure of being put on the spot.
Don’t bury the lede.
What’s worse than knowing you’re in trouble with your parents? The uncertainty of wondering if you are—and waiting to find out. As parents, it can be tempting to delay delivering tough news to protect our children from feeling upset or to avoid a challenging conversation ourselves. But holding back heightens anxiety for your teen, leaving them tense and bracing for a possible blowup rather than addressing the issue directly.
Suppose you’re concerned about your teen’s schoolwork—whether because of a troubling progress report, an unexpected test score, or (as in my case) a call from the school about the state of their locker—it doesn’t help to withhold this information. When you share your information directly, you create an opportunity to discuss it collaboratively. This process usually happens in two stages: sharing the information and then discussing it. Giving your teen time to process the news and have an initial emotional reaction allows them to be more prepared to discuss it rationally later, which leads to a much more productive conversation.
Explain your perspective.
When sharing concerns or frustrations with your teen, try saying, “The story I’m telling myself is…” This powerful approach allows you to express your worries while acknowledging that other interpretations or perspectives may exist. It gives your teen room to agree, disagree, or offer additional context, which feels less confrontational than a direct accusation. This phrasing shifts the tone from making a judgment to seeking understanding.
For example, you might say, “The story I’m telling myself is that you haven’t been doing your math homework because you’re spending too much time playing video games.” This approach opens the door for your teen to provide insight into what’s happening. Maybe they’re struggling with the material or feeling overwhelmed with other responsibilities. The goal is to understand their situation better so that you can provide the proper support.
While consequences are sometimes necessary, creating a safe environment encourages your teen to be honest. Over time, this openness can help them develop self-awareness and start to recognize and question the narratives they tell themselves.
You don’t ‘get it,’ and that’s okay.
I don’t know what it’s like to be a teenager in the 2020s, and chances are, neither do you. Most of us reading this remember life before smartphones. When we were teens, our most embarrassing moments weren’t documented by our peers and immortalized on the internet, bullies couldn’t harass us on social media 24/7, and our schools didn’t have active shooter drills. Teens today face unique pressures, from social comparison to academic demands and the constant connectivity that can strain their mental health. The collective trauma of COVID and increasing political polarization have only made being a teen more challenging.
We simply don’t know what it’s like to be a teenager in today’s world, and it doesn’t do any good to pretend that we do. But that doesn’t mean we can’t empathize with them. It’s essential that we do! Share your experiences from your teen years—not just the highlights, but the struggles too—while remembering that you don’t fully understand their reality. Acknowledging this creates space for authentic curiosity and opens up opportunities for you and your teen to connect on a deeper level.
Be patient, and remember what’s important.
Sometimes, your teen simply isn’t ready to talk. You may ask all the ‘right’ questions and create all the ‘right’ opportunities, but that doesn’t guarantee they will open up. My parents endured many of my ‘Fines’ and ‘Whatevers’. As frustrating as that must have been for them, they always ensured I knew they loved me and accepted me for who I was.
Even if your teen isn’t ready to engage, small gestures—like offering a snack during homework or inviting them for a walk—signal you’re consistently available. Remember that your teen is navigating immense cognitive and physiological changes amid social complexities, rigorous academic expectations, and an increasingly uncertain world. When you are patient, consistent, and supportive, your teen learns to trust that sharing their thoughts, feelings, and experiences is safe. Eventually, conversations about school will become more meaningful than just ‘fine.’
Travis Minor, M.Ed., is the founder and owner of Open Door Education, a tutoring firm that provides organizational coaching, academic tutoring, and test preparation to students in middle school and high school.
