The Journey to Raising Teenage Boys – Part 1 Honest Conversations

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I am no stranger to boys. I’ve been around them and playing with them my entire life. I’ve now been blessed with 2 myself who are starting into their teenage years. I often have people tell me how polite, well behaved, well rounded, well spoken, well adjusted my kids are and almost just as often get the question “how are you doing that?!” I thought I’d try and answer that question with some things we’ve purposely done as parents from the beginning.

Raising teenage boys who have open conversations with their parents (to read BEFORE your kids are teens) - at allfortheboys.com

Let me start by saying that I am in NO way an expert. Probably far from it. My kids are in no way perfect. None of us are. We make mistakes, and we apologize for them. My kids apologize to us and we sometimes have to apologize to them. Usually when someone responds with a compliment I think “Yes, but you should see us at home” lol!

These are just some things that I tell friends and family when they ask about having boys and dealing with them getting older (filtered a bit as to not completely embarrass them). Probably the only un-solicited advice I’ll ever give someone is do what works for you and your family. This is just the way WE do it. If you like these I’ll write more (just let me know in the comments) but to start let’s talk about how I got to the point where I can have honest and open conversations with my teenager(s):

Start the open conversations when they are young with age appropriate answers. We started VERY early on answering any question they had with open and honest (but age appropriate) answers. We had lots of very interesting and open talks on the drives to school starting in kindergarten. Everything from food, religion, politics and yes sex too. My oldest is very scientific and wanted information at a young age. In kindergarten he was totally fine with learning about cell division. I knew he was seeking an intelligent scientific answer not necessarily the “birds and the bees” talk (though he did know more about animals at this point because of National Geographic). Now that they are older conversations are less filtered and more honest.

Does this make for some uncomfortable conversations? YES but that’s what we wanted right? I want my boys to know that if they come to me to ask a question about something they heard from their friends, that I’m going to give them the totally honest answer (as uncomfortable as that may be). This is something that I really believe would not be possible if we hadn’t started having these conversations with them at an early age. There is no switch to turn on when these conversations start. That meant purposely starting conversations but also letting them join in on conversations that my husband and I are having. Sometimes they listen and bring up questions or comments later and sometimes they interject with their thoughts while we’re having the conversation. There was little division in “kid conversations” and “adult conversations” in our family. I believe this not only helps them be open to talking with us but helps them conversationally with other adults.

If you have (or remember being) a teenager you know that somewhere along the way your teenage brain thinks you know a LOT more than you do. With that, we have to remind our kids often that just because they feel strongly one way that doesn’t mean that others feel the same or that they are even right. This has started a desire within them to research and learn more, to build their opinions based on facts and information – not from memes they saw on the internet.

Do I think that my kids will come to me with every single problem they have? No. I hope they will but they likely won’t, so besides starting very early with open and honest conversations, I also try to make sure they have honest relationships with adults I trust. Aunts, uncles, grandfathers… we have the luxury of having a great family but we also have people in our lives that we choose to be there – friends from school and friends from church that the boys have developed some (healthy) relationships with.

Raising teenage boys who have open conversations with their parents (to read BEFORE your kids are teens) - at allfortheboys.com

Thinking back I don’t think I ever answered a question with “you’re too young to know that”. That instantly turns them off and puts up a small portion of a barrier that eventually would be so big they’d stop asking. I tailored answers to their age sometimes giving an answer that might be slightly above what they wanted to hear but important for them to know so they don’t run around using certain phrases. I’d rather my boys know what they really mean than run around school using phrases they think are cool or funny without knowing the true meaning or origin. This comes into play with derogatory words as well.

Basically we started conversations early, are honest with the answers and make sure they have people in their lives they can ask questions that they might not want to ask us (though we haven’t gotten there yet and I’ve answered some very weird questions especially after the 5th grade health class – you know the one).

Do you think your teenage boys can come to you with any question? Do you have advice for other moms on having open conversations with teenage boys?

Raising teenage boys who have open conversations with their parents (to read BEFORE your kids are teens) - at allfortheboys.com

Note: I am really just in the beginning of this journey but I feel like a ton of parenting is done in the early years. Now it’s helping them navigate becoming who they are, making sure they understand the consequences to the decisions they make and loosening the reigns a little to allow them to make mistakes (hopefully mild ones in the grand scheme of things) and learn from them.

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Allison Waken is a wife, mom of boys and Phoenix, AZ native. She has been creating inspiring content for All for the Boys since 2011. Allison loves travel, movies and spending as much time as possible with her family while she can!


  1. Great article. Having four boys ages 20-8, it’s always helpful to hear how others are navigating. We can all glean from each other!

  2. Thanks for the perspective. We have one 12YO boy and I seem to see LOTS of advice on parenting tween/teen girls but not a lot on boys (why I love you blog BTW). As an only child, our son has been part of most of our conversations from an early age. He is pretty opinionated but I’ll say his positions are rather well thought out for his age. One question for you…how are you handling the ‘know it all’ streak? When mine starts to STATE AS FACT his opinions, I’m trying to redirect to research(as you said) and instill that one book/movie/news report is one side of the story. I find myself loosing patience…any tips on the know-it-all tween without reverting to “I’m older than you” speech?

    • I SO feel you. We try to make sure we talk about how it’s hard for things they read and see NOT to be biased one way or the other and do lots of re-directing back to read from other sites. If it’s a big deal, my husband or I will try to find articles completely opposing his opinion (whether we believe it or not) so that he can see that there are well thought out ideas and opinions from the other side. Sometimes I will stop a conversation if it’s going nowhere and bring it up later. I don’t want him to think that his feelings are invalid, but yes, they do need to realize that they are only 12 (or 13 or whatever) and that they still have a lot of life to live. We also talk about how some of our opinions have changed as we got older. I definitely want them to think that they can voice their opinions but still be respectful of others. It gets even tougher when they have friends with the same strong opinions. I don’t know if that helped you at all, but that’s what we’re doing for now!

      • it did. THANKS! I hadn’t thought of sharing how my views have changed over the years…that’s brilliant. I do want him to realize his voice and opinion matter. I also want him to be able to listen to the opposing view with an open mind and be self-confident enough to admit if he’s changing his stance without being belittled..something society is NOT modeling well right now. Oh, the struggle is real! thanks for the continued insight!

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