Raising Teenagers and a Toddler—At the Same Time 

From university applications to bedtime tantrums, raising teenagers and a toddler simultaneously is a masterclass in chaos—and unexpected joy. 

In 2021, I was a divorced single mom to pre-teens, Olivia and Theodore. I shared 50/50 custody, and we spent our post-lockdown days together running errands, dining on patios and embracing in-person classes. But when the kids were at their dad’s, I’d gleefully swipe right on Bumble. I honestly enjoyed the chance to meet other people outside my circle, and I was excited to fill my weekends with evening drinks and coffee dates. As part of my profile setup, the app asked my plans for children. I confidently selected, “Have kids and don’t want more,” and I even approached my GP for a referral to get my tubes tied.  

And then along came Edo Cuallo. A motion designer that loved hiking, cooking and (irritatingly) could hold a handstand longer than I could. I was hooked. After dating exclusively for a year, we traded in our individual apartments for a house that comfortably fit the two of us, my kiddos, my two Siamese cats and Edo’s loyal pug.  

Hello, Post Twist

When I finally got the call to schedule my surgery, Edo and I sat down to have the chat. He had embraced the stepdad life at 39, but when I asked if he’d be disappointed to not have a baby of his own, he replied, “I always thought I’d be a good dad.” My ovaries screamed.  

As the eldest of three, I had always wanted three kids, but economically it never made sense. When Theo was born, I was earning $40,000 as a graphic designer, while paying $2,100 in monthly childcare. We’d confidently closed that door when I was 26.  

A decade later, life felt so much easier. With very little debate, I optimistically toggled my Natural Cycles app from Prevent to Plan, and we started TTW (Trying to Whatever). If we were meant to have a baby, we’d have one.  

Six weeks later, I was pregnant.  

Fast forward to today, I’m in my last year of my 30s, and that same house is bustling with activity. My 17-year-old will graduate high school in the spring and is narrowing down which universities she wants to apply to. My 13-year-old spends his afternoons biking midtown with pals and blowing his allowance on bubble tea. And our two-year-old, Alfonso, is a tornado that leaves a trail of Hot Wheels in his wake. 

Finding Calm in the Chaos 

As a VP at a midtown ad agency, Central Station, I opted for a six-month maternity leave. Working from home allowed me to schedule nursing breaks between meetings, manage my team and still have a quick midday lunch with Edo. At 5pm, I begin my “second shift,” transitioning to playtime, homework checks and extracurricular coordination. I’ve mastered the art of compartmentalizing my day, to be as present and engaged in the moments that matter.  

Surprisingly, I’ve found so much ease and predictability with the new baby. It balances the chaos of navigating teenage drama and makes me feel like I can still do some things right. The seriousness of life is lightened daily with the silliness that Alfonso brings. 

We also have new family routines. We prioritize sit-down meals (before Alfonso’s bedtime), to catch up and check in with one another. By the time our kitchen is restored post-dinner, the big kids have fled to their devices or friends. And unlike the parenting adage to “sleep when the baby sleeps,” Edo and I almost always spend 8pm to 10pm catching up on work.  

The daytime requires flexibility, too. I’m writing this article on a Sunday afternoon, as I sit field-side at one of my daughter’s rugby tournaments. Between games, I check emails, fill out back-to-school forms and plan our calendars. Edo’s at home with the boys, championing naptime and laundry, while prepping for his Monday deadlines. There are less date nights but undeniably more joy. 

Raising Teenagers and a Toddler

I haven’t slept more than five hours straight in years. Most evenings I lay awake worrying about the best way to parent my teens through drug use, sex, friendships, social media and their studies (only to be woken by a headbutt from my toddler hours later).  

Our days may be affected by sleep schedules, but having been through it three times, I really don’t fuss the way I did in my 20s. I co-sleep, despite my eldest two being rigorously sleep-trained. I know he’ll stay in his crib when he’s ready to, and I refuse to waste precious energy speeding up that timeline. 

Stress is a constant companion and I’m certain I’ve visibly aged a decade in the last three years. Yet, I never regret the time spent laughing, coaching and loving my kids. It has been the greatest, most rewarding job of my life. Would I like to get back to adult gymnastics classes, or curl up more often in the Cineplex VIP with Edo? Absolutely. But this time is fleeting, and I know too well that the current demands will fade. It’s just not this season of life, and that’s okay. I’ll still pause to smell the flowers. 

After birthing a child in three separate decades (2008, 2012, 2023), Jenn Dunstan declared that enough was enough, skipping into surgery to remove her fallopian tubes last spring. She lives and works in midtown Toronto, is an insufferable foodie, and refuses to get her driver’s license.