Education & Family

The Emotional Rollercoaster of Teaching Your Kid to Drive

Baby books mark all those important milestones—first word, first steps, first food, but what about the milestones that suck the breath out of your body and make it hard for you to function?
—Illustration by Montse Galbany

The very first day Milo Oliver Diamond rode in a car he was two days old. I sat in the back of the Honda Pilot next to his car seat, as first-time moms are wont to do, and stroked his fat little cheeks as we made the methodically slow drive (as first-time dads are wont to do) from St. Joseph’s Hospital in Towson to our rowhouse in Canton.

Milo hated the car for the first two years of his life. He would cry so much that I would frequently pull over and inspect him from head to toe just to make sure he wasn’t hurt. Then I started driving with one hand on the wheel and one arm contorted behind me, touching the top of his head. That seemed to appease him.

Fast-forward 17 years and now I’m the one crying in the car. I’m just kidding (kind of), but seemingly overnight that baby has grown up to be taller than me—a smart, handsome, strongly opinionated teenager with stellar grades and a girlfriend. And he wants to drive my car.

How did we get here?

The first thing you do when you have a new driver in the family is slap on one of those magnetic stickers. The one affixed to our Toyota minivan is bright yellow and announces: STUDENT DRIVER. PLEASE BE PATIENT.

In Maryland, a learner’s permitted driver must complete a minimum of 60 hours of driving practice, so we squeeze in drives as often as we can—even at 7 a.m., when so many parents do the same early morning dance with their kids. Milo drives to school, with me in the passenger seat. When he pulls up, it’s like a fire drill as we get out of the car—I’m usually in some sort of half-dressed mom get-up (pajama pants, sweatshirt, oversized sunnies, slip-on shoes)—and I slide into the driver’s seat for the ride back home to scoop up our middle school twin boys. Milo grabs his backpack out of the back seat and grumbles goodbye, following his sister toward the school’s front door. Why did I just let that half-awake human drive my $45,000 minivan?

You never say your kid’s name more than when you’re teaching them to drive. There’s the chill, “nice job Milo” you imagine you’ll be uttering after a relaxing spin around the neighborhood as you both emerge from the car smiling and laughing and bonding over this life passage. And then there is reality: “Milo, Milo Miloooooooo. Milo! Mi-lo. MILO OLIVER DIAMOND!” At this point, I’m angry. He’s angry. And okay, I’m a little angry at myself.

Yeah, it wasn’t supposed to be like this. I mean, I wish I could say that I magically exuded a sense of Zen while teaching my son to drive. I don’t have a lot of anxiety, but I can get exasperated when I’m frustrated or stressed and that seems to increase tenfold when I’m in the passenger seat. And Milo, like most teenagers, is a confident narcissist. As his abilities have grown, his willingness to accept constructive criticism has decreased. He takes to driving tips like Julia Child might take to a critique of her beef bourguignon. But I’m paying for the ingredients, Julia.

As stand-up comedian Jim Gaffigan once said, “Parenting is hard the entire time. The task changes though. When you have a baby, you’re like, ‘This is the hardest thing I’ve ever done but I would do anything for this baby.’ And when you have a teenager, you’re like, ‘This is the hardest thing I’ve ever done but I don’t want to go to jail for murder.’”

I decided to reach out to a professional to help me get a grip on my emotions.

“It’s such a time of mixed feelings,” says Jason Parcover, assistant vice president of student well-being at Loyola University Maryland and the father of three. “My youngest just got his license a couple of months ago—so this is near and dear to me.”

Talking to Parcover is so calming I almost ask if he can teach Milo to drive. He sympathizes with the “it’s complicated” feelings I have.

“There’s so much to celebrate and feel happy about, but we also worry and stress about our kid’s safety,” says Parcover. “And there’s a little bit of loss sprinkled in there.”

But everything we’ve taught them to this point is to help them get launched into the world, he reminds me. A driver’s license is just one more way to help them grow.


Driving is a topic of conversation in all my social circles—not just because, much to our collective surprise, we’re all old enough to have kids behind the wheel…but because, okay, I’m constantly bringing it up. One friend told me that back when she was learning to drive her mom would gasp. Constantly. Didn’t matter if she was changing lanes. Gasp. Stopping at a light. Gasp. Or turning down a street. Gasp

Another friend would have her kids practice by driving through a local cemetery. No live people, no traffic, no lights. It was the only place she felt like she wasn’t going to die if she drove with them. (Yes, she sees the irony.)

Back in my learning-to-drive days, my own mom was a frequent grabber of the “oh shit” grab handle and famous for hitting the phantom brake pedal on the passenger side that she seemed to think would somehow slow the car down if she really believed.

Aaron Henkin, a senior producer at Johns Hopkins’ Berman Bioethics Institute’s iDeas Lab, told me he goes into a catatonic state when he drives with his kid. Kind of a paralyzing immobility. When I relay that story to Milo, he says, “You’re whatever the opposite of catatonic is.” (He doesn’t mean it as a compliment.) He thinks I’m hysterical, with a side of helicopter parenting thrown in.

He’s not wrong.

Baby books mark all those important milestones—first word, first steps, first food, but what about the milestones that suck the breath out of your body and make it hard for you to function? The first time they drive at night, the first time they drive in the rain, the first time they drive with a friend, the first time they drive by themselves, the first time they drive on the highway. We once celebrated milestones with a camcorder and a Skype with the grandparents. Now we monitor them with Life360, a family location app.

For Milo’s sake, I initiated the rule that if both my husband and I were in the car and Milo was driving, only the person sitting next to him in the passenger seat could offer feedback. No backseat driving. But I soon realized my husband wasn’t watching Milo as carefully as I would when I was in the front. (Whether that’s the reality or not is not up for debate.) So, I botched the very rule that I implemented. I’m vocal. And nervous. There are so many scenarios that play in my head. Most important is for Milo not to die. Then for someone else not to die. Then for my car not to die and then for someone else’s car not to die. That is my all-consuming thought process.

“So, death, murder, and destruction,” my friend Hailey teases me. Yup, while also appearing positive and upbeat: “You are doing great, Milo!”

I know I may seem a little ridiculous. But the fear is rooted in actual stats, and I’m acutely aware that it’s the most dangerous thing he’s done to date. According to the Federal Highway Administration, over 8.3 million drivers in the United States are between the ages of 16 and 19. They make up approximately 3.7 percent of all drivers in the country. In that sense, Milo is no different than the millions of other teens who are learning to drive. But it feels different because he’s mine.

What’s more, the AAA Foundation for Traffic Safety reports that drivers between the ages of 16 and 17 are more likely to be involved in car accidents than drivers from any other age group. Additionally, teen drivers cause more injuries and deaths than other drivers, including injuries to themselves. Deep breath.

On the other hand, there is something poignant and powerful about this stage. At a time when Milo seems to be pulling away from us with his own identity, his own friends, college visits—him needing me as his driver feels like all I have left. It’s time together when he forces me to listen to his music and I force him to tell me about his day. Soon he won’t need me anymore.

And when I see him in the car, window down, music on—I get it. Because sometimes when I’m driving, I can still remember the thrill of being 16 and knowing that you could literally drive anywhere. (I never did—but I could have.) I’m not sure there’s any other thing where you can experience that sort of freedom at this age. It’s the opposite of being a driver in your 40s, when all I do is drive other people (my children) places. It feels like the reverse of freedom.

But how do you let your most prized possession just go? How do you trust the other drivers on the roads—the ones I see running lights and passing on the shoulders, aggressively tailgating, and staring at their phones while driving?

In the end, you just have to. I keep picturing one of those giant Macy’s Thanksgiving Day Parade balloons—and releasing one of the tethers. And one day, if we’re lucky, most of those tethers will be freed and he’ll be an excellent independent adult. But right now, I’m exhausted and a little sad, as I still try to hold onto that little human who once needed my hand on his head to tolerate riding in the car.


When I decided to write this essay, I would scribble notes while Milo drove. (As Nora Ephron famously said, “Everything is copy.”) I tended to get a little melodramatic, writing things like, “This is Dante’s Inferno—and his descent through the nine circles of hell will eventually take us to the center, where Satan himself resides.” Then I decided driving with a teen is more like a 12-step recovery plan—and you finally have to land on acceptance.

So little by little, I’m learning to let go. Now I find myself asking if one of his friends can drive him home after practice or to his social justice seminar when his three siblings need to be somewhere at the exact time he needs a ride. Necessity is the mother of invention—or finally realizing how nice it would be to have another driver in the family. (Yes, I’m ignoring how much my insurance bill is going up.)

He still makes rookie mistakes. Pulling into the driveway the other day and forgetting to put the car in “park” or driving too close to the shoulder and almost taking off my mirror. But I realize it’s impossible to teach intuition. I’m a good driver—I learned to drive in a Taurus station wagon we called Big Bertha—because my dad was a great teacher but also because I’ve been driving for over 30 years. We also learned back when there were no cell phones, no smart cars. My first car was a Honda Civic stick shift with a CD player and after-market sunroof.

As time goes by, I’ve seen Milo’s confidence building, but I still remember those early days when we sat at a stop sign for a good five minutes waiting for what Milo deemed the perfect time to cross one lane of traffic and turn onto another. “I’m not rushing you, Milo, but at some point, you have to trust yourself to go,” I told him. And he did. He’s come far—we both have.

The other day we were in the car with Milo behind the wheel. I was in my usual co-pilot seat, and Willa, my 15-year-old, was behind Milo. Milo was playing music that I don’t hate, and I actually felt—yes, relaxed. I think I let out an audible sigh.

Suddenly, a sweet voice piped up from the backseat. “Mom, you know I can start driving soon.”