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This post has been updated. but it’s still the best way that I’ve found to connect and bond with a teenager.

As our four children are getting older, parenting two teenage sons, and another two following close behind,  I’ve thought about how I can be the best mom for them. 

I’ve prayed that I can teach them what they need to learn before they are grown.  I’ve worried over things that I should have or could have done better over the years.   I’ve hoped and prayed that we are raising them to be kind, responsible, caring adults.   

While there are things that no one tells you about parenting a teenage boy, there are also things that you learn along the way… things that you learn are more important than anything else. 

Thankfully, I feel like the older they get, the more I am learning.   As our older kids are now in their early teenage years, I feel like I know them better than ever before.   

How to connect with your teen

Those worries of what the teenage years are going to hold for us have arrived, but it turns out I didn’t need to be worried after all.   The tween and teenage years have been some of my favorites.   I’ve found that by putting in the hard work when they were young, we are reaping the rewards now that they are older.   

The teenage years get such a bad name, don’t they?   We worry about them, we fret about them, and we dread them, but it just doesn’t have to be this way.  Yes, it’s different… much different, but it’s also been wonderful.   You can have real conversations with a teenager.  You can talk about things that really matter, or you can sit and talk about things that don’t matter at all.   

I’ve mentioned it before, but I think that all of those rules & routines that we put in place when they were younger pays off during this stage in their lives.    Some stages were trying (to say the least), but now that our boys have turned into young men, it’s like the hard work is paying off.

The best thing you can do to stay connected to your teenager 

Be there to listen… when they are ready to talk, even it if is late at night. 

When I was talking to Mickey the other night, I said: “If you had to pick just ONE thing that kept you close with the older boys, during these tween & teen years, what would it be?”   

He said, “The rides to and from practice.  It’s when we talk.  What about you?”

My answer was a no-brainer: OUR LATE NIGHT TALKS.” 

I feel that the older our kids get, the more I get to know them, and the more they get to know me.  Our teenagers would rather hang out with us than anyone else.  He’d pick a card game with his parents over playing a video game with his friends.  

My favorite part? 
He always chooses to have a late-night talk with his mom over staying up to watch a movie, watch TV, or really do anything else.      


Talk to your teenager at night

 It happens every night.    After I tuck the little ones into bed,  clean up the house a little, and get things ready for the following day, it’s almost time for our older kids to go to bed.   

I still put them both to bed…

  • It takes about an hour…
  • I’m exhausted (physically & mentally) and I’m ready for bed myself…
  • But, I wouldn’t change a thing.   

What a Teenage Bedtime Routine looks like in our house… 

When I tell them it’s time for bed, they know that they need to go to their bedrooms and read until I come into their room.  I start with our almost-teenager.  Not quite a teenager, but as close as can be.

I’ll go to his room first and just sit on his bed.  (I turn his BedJet on high-heat to try to stay warm while I’m in there since he has his ceiling fan on full blast every night and I don’t like to be cold.  My boys both know this, so they usually get an extra blanket ready for me when I come into their rooms.)

When I’m all snuggled in, I say something along the lines of “So what’s new?”  Or “What did you guys do today?”  

That’s it.

That’s his cue to talk and my cue to listen.

It’s my way of saying, “I have my ‘listening ears on, and I’m ready for whatever comes.”  

The key is to be patient, to wait, and to listen.   

Usually, it takes a couple of minutes to get started.  He’ll ask me what I did, or he’ll tell me a little about school, but it’s not long before he really opens up.

For the next 30 minutes or so, he dominates 90% of the conversation, and I listen.  


I give a lot of “You’re kidding me.” Or “That’s so cool”   I interject a few stories of when the same thing happened to me, or I share advice if I feel it’s needed.   For the most part, however, I just let him talk.

This is also the time where I bring up those awkward topics that he doesn’t want to talk about.  They handle it much better when it’s just the two of us, and the chance of a younger sibling coming in is extremely rare.  (Tip: If you can act like these things aren’t too awkward, he won’t squirm too much when he hears you mention the topic).

When I’m finished in his room, I tuck him in, kiss his cheek, remind him to pray, & tell him goodnight.

He usually reads for a few more minutes (another chapter or two) while he waits for his dad to come in and say goodnight.

Then I head into our teen’s room.  I go to his room last because he stays up the latest. 

I do the same thing in there… I get into bed, cover up with every blanket that I can find (because he has his fan going, too) and I get ready to listen.

For the next 30 minutes, I’m giving him all of my attention.  

He starts talking… he tells me so much during this time.  He also asks a lot of questions and listens to my stories about similar things.  

This is when I hear about his friends, his interests, his concerns… he tells me so much during our talks at night.

Why do teens want to stay up late? 

Did you know that there is a scientific reason that your teen wants to stay up late? explains it well:   “Sleep is regulated by two body systems: sleep/wake homeostasis and the circadian biological clock.   

Changes to this circadian rhythm occur during adolescence when most teens experience a sleep phase delay.   This shift in teens’ circadian rhythm causes them to naturally feel alert later at night, making it difficult for them to fall asleep before 11:00 pm.” 

Now, we don’t follow it exactly.  Our kids still go to bed around 9:00 on weeknights & 10:00 on weekends, but they don’t have to go right to sleep… they are welcome to read in bed.  

Why should I stay up late to talk to my teen? 

I know that we are tired at bedtime.  Trust me.   The thing is – you aren’t going to get this opportunity back.    These late-night talks, sitting on his bed, just listening. 

Connecting.   Bonding.   Understanding one another.  Gaining (and giving) respect.  Giving advice to someone willing to listen, because we waiting until they were ready to hear it.  Showing him that you are there to listen, support him, and talk to him.   
Showing them that they always have a place to go, a person to go to, when they need it.  

Making mom laugh!

I’d never give it up.

The moral of the story is that every night, it takes me an hour to put these two kids to bed. 
I’m exhausted.
I want to be going to bed myself.
I am not always interested in the topic at hand (cars, buildings, sports).

This is when the connection & bonding happens.

I truly believe, that these late-night conversations, when I’m exhausted and they are not, are when the relationship builds. 


What if I want to go to bed before them? 

There are nights when I’m just too tired to stay up until they go to bed.   It’s ok.  We make it work.   On those nights, I say, “I’m going to bed.  If you want me to tuck you in so we can talk, you need to go to bed now.  You can stay up and read after I leave.” 

They ALWAYS pick to go to bed if it means that I will go with them to talk.   

Talking, late at night, is one of their favorite times of the day (if not their very favorite), and it is mine, as well.

Of course, some nights it just doesn’t work out, and that’s ok.   We just make it work as often as we can.  

They will reciprocate 

If we spend time with our kids, if we are involved in our teenager’s lives, if we support them, listen to them, and remind them that we are there for them, they will reciprocate.  

Yes – we are still the parents.  Our teens still have rules and boundaries.  They still have the same phone rules (no phones in the rooms, I monitor them, I set it up so they can’t text at night, etc…).   They still have a bedtime, even on the weekends.  They still have to ask me before they have a snack.   
They still have the rule that once we tuck them into bed, they have to stay in their bed (even though someone will still come out, from time to time, for “a glass of water” or to tell me “something that they forgot”). 

It’s not perfect, but it works for our family.  

At the same time, all of those years of enforcing the rules & boundaries when they were younger and thought they knew what was best, has paid off.     

The late-night talks are worth their weight in gold. 

All of that time, sitting in their rooms at bedtime (from the time that they were old enough to talk), just listening to them, has paid off.  

As you know, if you’ve read my post: “Mommy, will you lay with me?”   this isn’t a new concept or habit for me, but it’s one that I am glad I stuck with. 

The older our kids get, the more I learn about them.  The more we grow as a family and as friends.   The more they come to me and ask for advice, knowing that I’m going to give it, but that I’m also going to listen & understand them… or at least they know that I am going to try.   

When you have “raised them up’ in the way in which you want them to grow, they will follow.   Now you can reap the benefits of that hard work… and enjoy the respectful teenagers you’ve raised. 

Ps- You are welcome to grab this free calendar: 30 days of one-on-one time with your teen. 

Son and Life calendar

Here are some amazing books about raising teenage boys:

Hi there!

I’m Becky, a former elementary school teacher turned certified child development therapist and blogger. I work at home with my husband and together we are raising (and partially homeschooling) our four children in the Carolinas. I love diet coke, ice cream, and spending time with my family.

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