Meaningful Conversations: Shifting from “How was your Day” to Fostering Greater Connection through Deeper Questions

“How was your day?”

“Fine.”

“Did you do anything interesting?”

“Nope.”

“Is school going okay?”

“Yes.”

Sound familiar? When you try to connect with your teen and are met with these responses, it can be incredibly frustrating, especially if you know that your teen does have a lot that they can share.

When you know your teen had a big math test or basketball tryouts or their first day at work, but they won’t open up, it can make you feel like your teen doesn’t trust you enough to share with you.

However, if you struggle to get your teen to say more than two or three words when you try to find out what is going on in their life, it might have less to do with your teen and more to do with the questions you’re asking.

When you ask the right questions in the right way, you can improve your connection with your teen and open the door to more meaningful conversations.

Here are a few ways to start:

Ask deeper questions

If you only ask your teen “yes” or “no” questions, don’t be too surprised when you receive a “yes” or “no” answer in response. Try asking deeper, open-ended questions that your teen will have to use more than a word or two to answer.

For instance, instead of asking did anything interesting happen, which could be answered with a simple “no,” ask them what was the most interesting thing that happened to them or what could have happened during their day to make it more interesting.

This will allow them to share something that happened, even if it might seem insignificant or small, and it will also allow them to tell you something that they may have wished would happen that day.

Try asking your teen one of these questions each day and see how they respond: 

  • What makes your favorite class so enjoyable?

  • What movies or television shows have you been enjoying recently?

  • What was the worst part of your day today?

  • If you could re-do three things about your day, what would they be?

  • What are you proud of yourself for doing today?

  • What was the most annoying thing that happened to you today?

  • If you could choose any of your teachers to have for all of your subjects, who would it be?

  • What are three things you are grateful for today?

Questions like these can lead to deeper conversations that will help you bond with your teen.

Be patient

Sometimes in an attempt to fill awkward silence or move past one-word responses, parents will rapidly ask questions without giving their teen a chance to really think about their questions.

For instance, when your teen says “fine” after you ask how their day was, you might quickly move to the next question or even end the conversation by saying something like, “that’s great” without realizing that your teen actually had more to say.

Feel free to take a pause, even if it is awkward, after your teen’s initial response to give them the time they need to process the answer to your questions and decide what they want to share. They might surprise you by adding more information when they’ve had a chance to think about what they want to say.

Their “fine” response could turn into “Fine...I actually understood what I was doing on my math test today so that was good,” or “Fine...I wish I had more time to eat my lunch, though.”

Be patient when you ask questions and don’t fear silence. Your teen might be more willing to share when given more space to do so.

Offer unconditional positive regard

Sometimes teens want to share personal information with their teens, but they are afraid of how their parents will react.

If you get upset and yell every time your teen shares that they did poorly on a test or a paper, then they will eventually stop volunteering this information. 

If you blame them or express judgment when they talk about a mistake they made during the day, they will keep their mistakes to themselves. 

Teens need to know that they have a safe space to share what’s going on in their world. Make sure you are able to be a safe place for them by offering validation and unconditional positive regard when they take steps toward having a meaningful conversation and relationship with you.