Trying to make meaningful conversation with teenagers doesn’t have to be like pulling teeth. It’s all in your approach.

By Leslie Josel
connect with teens
Credit: Illustration by Julie Houts

Ever heard of a “momversation”? Me neither, until my son casually floated the term when we were out to lunch at a restaurant.

But first, a little backstory: Our household is a busy one. Two full-time working parents, business trips, schoolwork, play rehearsals, ongoing construction (don’t ask!), plus seemingly endless amounts of other stuff. You know the drill. Busy.

I was feeling particularly disconnected from Eli, and desperate to resolve some of the endless questions and decisions that were bubbling up throughout his senior year in high school. Truth be told, I don’t do well with the unknown. By nature, I’m a planner and an organizer and the consummate list maker—and did I have a list for my soon-to-be-graduating boy.

So when I realized his school break offered an opportunity for us to spend extra time together, I scheduled a few local outings. Away from the house, we’d get the chance to really talk—or so I thought.

Right after the waitress took our lunch orders, I whipped out my list and got cracking. “Have you thought about what colleges you might want to eliminate from your list? Any decision as to whether you want to do the senior internship program? Are you going to perform a monologue for the audition or play your bass?” Without missing a beat, he replied, “Is this going to be one of our ‘momversations’?”

I bit my tongue. My rep is no secret, but Eli would NEVER refer to talking to my husband as a “dadversation”! However, his pointed question made me realize that I’d become too predictable in my patterns, and my all-business MO was almost certainly undercutting the connection between us. As soon as I asked, “Can we go over a few things?” my son intuited that our conversation was about to become a series of rapid-fire questions, and that made him prone to mentally check out. He is all too aware that I’m always thinking five steps ahead in order to feel prepared. Frankly, it’s exhausting. And if I’m exhausted, well, I’m guessing he’s exhausted by me. Not a great foundation for authentic communication.

So, did we have our momversation? Actually, yes. Several of them, and good ones. Just not that day. That day, I approached much more softly. Instead of a board meeting atmosphere and endless rounds of questions, I put Eli in charge of what he wanted us to talk about and let the conversation flow naturally. Admittedly, I did not get all my answers, but that’s OK—the rest waited for another day. Progress.

7 ways to better connect with your kid

connect with teens
Credit: Illustration by Julie Houts

1. Ask before offering advice. Yes, you heard me. This was the hardest thing for me to learn to do. I’m a fixer by nature and always want to jump in with a solution. But offering unsolicited advice almost always shuts down the back-and-forth. As my kids got older, my rule of thumb was to ask them first, “Do you want my advice, or do you just want me to listen?”

2. Meet them where they are. I’ll give you an example: When it comes to travel, my son and I have nearly polar opposite styles. He's all go-with-the-flow, we'll-get-there-when-we-get-there. Me? In some ways I love the planning almost as much as the trip itself, and happily research what we’ll see and do months ahead of time. But then on one getaway, seeing the relaxed, easy look on Eli’s face got me thinking, “Maybe I need to dial it back a little and not have every minute pre-planned.” Leaving some air in our schedule meant we could grab last-minute tickets to a basketball game that ended up being a highlight of the week. Applying this principle to life at home has yielded similar pleasant surprises.

3. Don’t take offense when your kids signal they need a break from you. In other words, if they pointedly put on headphones or turn on the TV or grab their laptop sometimes, do your best to not take it personally. Being chill and respecting their telegraphed need for space conveys that you get them, or are at least trying to.

4. Give them opportunities to rise to the occasion. Though it felt super nerve-racking at the time, we let my son fly by himself for the first time at age 16. My husband brought him to the airport and made sure he got through security. After that, Eli was on his own. And while he admitted he had to keep track of a lot, he appreciated our trust that he could manage it.

5. Establish reasonable rules that acknowledge each other’s priorities. For us that meant Eli not scrolling on his phone while I’m driving him somewhere—I want him to stay engaged and keep me company—and me not dragging him on endless errands. Do we keep to the rules? Well, he uses his phone from time to time and I bring him to a few more stores than I should. But being aware helps us both mostly comply and fosters positivity.

6. Go for open-ended questions. Nothing brings conversation to a screeching halt faster then asking yes/no questions. Instead, try dialogue starters such as,  “So how do you feel about…?” to get a chat flowing. For younger kids, I love using a rating scale to kick things off. For example, inquire, “On a scale of one to 10 with 10 being, like, the best day ever, how was today? Why that number?”

7. When all else fails, buckle up. As kids get into the teen years, don’t underestimate the potential power of peaceful moments in the car. Conversation often flows there more easily because sitting side-by-side precludes the expectation of much eye contact. If the chatter dies down, there’s music to fill the void and you might even end up singing. And in the end, parenting is never about the destination, always the journey.

About our expert

Leslie Josel
Credit: Photo courtesy of Leslie Josel

Parenting expert Leslie Josel has been working with teens and their families since 2004, when she started an educational company called Order Out Of Chaos. She offers a ton of free resource material for parents at