50 of the Best (and Fun!) Questions To Start a Conversation With Your Teen Boy

50 Questions Moms Should Ask Teen Boy

Teen Boys.  They're moody, smelly, and silent.  But they're also funny, smart, quirky, and silly.  And we love them.  But sometimes, we feel as though we can't reach them through their wall of silence (and their earphones and headphones).  And we miss that closeness. 

If you haven't already read my post on supporting our boys through adolescence and how to strengthen the mother-teen boy and father-teen boy relationship, click here.

My 14-year old plays baseball.  His school season was about to wrap up, and I decided that I wanted to memorialize the season in some way.  I decided to make a video of the season, complete with video interviews of the boys.  I set up a schedule to interview two boys per day after practice and e-mailed all of them with the schedule (with their parent's permission, of course).  

I thought long and hard about what I wanted to "get" from them.  I didn't want to ask the usual "what do you have to say about this season?" or "do you have anything you want to say to your parents, the coaches, or your teammates?".

I dug up a bunch of baseball-related questions.  For you baseball moms, the questions I asked were:

When does a batter get a "Golden Sombrero"?  This one was hilarious, I got footage of several players saying "What is that?", "Is this a joke"?  LOL.  (Answer:  4 strikeouts in the same game)

When a batter hits below .200, he is known to be below what?  Most didn't know the answer to this one.  (Answer:  The Mendoza Line)

What does "cheese" mean in baseball?  This was another funny one....I got all sorts of responses.  (Answer:  an overpowering fastball)

What are 7 ways to reach first base?  (Answer:  hit, error, walk, fielder's choice, hit by pitch, dropped third strike, defensive interference)

The four baseball questions provided great entertainment, both in the video and for me, personally, while filming them!  I also asked each player to pick a teammate's name out of a jar and told them to tell me something about that player (a trait, a memory, a funny story, etc).  It was a ton of fun to see them talk about their friends and teammates.  Most importantly, though, I wanted to infuse their personality into the video.  I'd see the boys only in passing, at practices and games, but never had the opportunity to talk with them one on one.  And I know many of the parents felt the same way!

So I combed through a ton of stuff online for questions to ask them.  Then, I compiled a list of 50 questions that I felt were appropriate (and "cool") for a teen boy.  I made sure they were pretty open-ended to get them talking and to avoid the short, one word answers.  I printed the questions, cut them up and asked each player to randomly pick one from a jar.  I can tell you from experience that these questions are GREAT for getting interesting, insightful, and sometimes hilarious answers from teen boys. 

For the end of season video, I put in snippets of the boys reading the questions aloud along with their answer.  The video was a hit!!!  Not only did the parents enjoy the video, but the boys had a blast watching their teammates on film.  (Fun fact: the boys loved to gather together and watch me interview their teammates.  Although I called only two boys to interview per day, I would sometimes have a whole bunch of them, curious and wanting to see their teammates squirm a bit.)

It was a ton of work but it was SO. MUCH. FUN.

I'm passing the 50 questions over to you so that you don't have to pore over websites to find good conversation starters.  I've done the heavy lifting for you!  I've listed 30 of the questions below.  If you'd like to get the entire list of 50 questions in a beautiful, colorful, 5-page PDF printable format, please opt-in below.  If not, refer to this post and get started.  Prep your son by telling him you have some fun questions to ask him and go for it during your commute or at the dinner table!

50 Questions to Ask Teen Son Opt-In Graphic.png

Here they are: (hopefully these will get your teen thinking and can lead to a deeper conversation--or at the very least bring some laughter to the car or table):

1.  What is a superstition that you have?

2.  If you could have a super power, what would it be? Why?

3.  What advice would you give to younger kids about middle school?

4.  If you were going to bury a time capsule, what would you put in it?

5.  What is the craziest thing you've ever done?

6.  If you could eat one food for the rest of your life what would it be? 

7.  What is your dream job?

8.  If you could make up a brand-new school subject, what would it be?

9.  Make up a new holiday. What are the traditions for your new holiday?

10.  What is one thing you don't know how to do, but wish you did?

11.  If you could trade places with anyone for a day, who would it be?

12.  Create a new cereal flavor and tell me about it.

13.  What is something you think that kids understand, but adults do not?

14.  Do you like how old you are in now or do you wish you were older or younger?

15.  If you could be famous for one thing, what would it be?

16.  If you won $1000, what would you do with it?

17.  What is something you're obsessed with?

18.  What is the best and worst thing about school?

19.  What three words best describe you?

20.  If you started a business, what type of business would it be?

21.  What is the strangest dream you've ever had? 

22.  What is the most annoying habit someone can have?

23.  If you could learn the answer to one question about your future, what would it be?

24.  What is the silliest fear you have?

25.  What weird or useless talent do you have?

26.  If you had a personal mascot, what would it be?

27.  You find a remote that can rewind, fast-forward, stop and start time. What do you do with it?

28.  Would you rather be able to teleport anywhere or be able to read minds?

29.  Who would be the worst person to be stuck in an elevator with?

30.  If you had three wishes, what would it be?

I hope you have fun with these questions and I sincerely hope that it helps to strengthen your relationship with your teen son!   Again, if you'd like a copy of five beautiful printable worksheets with all 50 of the questions, please opt in below.  Enjoy!


Some questions are my own.  Others were sourced from:

1.  Merrill, Mark.  "The Best Conversation Starters for Teenagers".  www.markmerrill.com.  http://www.markmerrill.com/the-best-conversation-starters-for-teenagers/  Web.  Accessed 10 May 2018.

2.  "250 Quality Conversation Starters". www.conversationstartersworld.com https://conversationstartersworld.com/250-conversation-starters/ . Web.  Accessed 10 May 2018.