Raising a Tween Who Listens to His Heart

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In the passenger seat of the car, my 13-year-old son, Jake, looked at me with eager anticipation. “What are we doing next Friday night, Mom?”

I took a moment to gaze at him, observing the transition from the baby with chubby cheeks to this young man with defined cheekbones and a hint of tween body odor. Just yesterday, I was glancing at him through the rearview mirror, cradled in his infant car seat.

“Not much planned. Why do you ask?”

He turned to look out the window, then back at me, inhaling deeply. “There’s a girl I want to ask out.”

In that moment, I realized my little boy was stepping into a new world—a realm of emotions and experiences that would soon take him away from the carefree days spent with his sister and her friends. I knew this day would arrive, where he would yearn to explore relationships beyond the innocent playdates of his childhood.

And so, the moment had arrived. He was ready to explore puppy love, and as much as I wished I could freeze time, I understood this was an opportunity for him to chart his own course, supported by his parents. Navigating dating can be challenging, especially when one is unsure of the process. I wanted to ensure he approached it with the same sweetness his father once showed me, starting with the basics—bringing flowers for his date.

Despite still envisioning him in his footed pajamas, clutching a Thomas the Tank Engine toy, I agreed he could ask the girl to the school’s Valentine’s event. The joy in his eyes and the smile spreading across his face tugged at my heartstrings, bittersweet as it was to see his affections begin to shift away from me.

When he mentioned, “If we go out for ice cream after, can you sit at another table so we can, you know, talk?” I had to suppress my initial feelings of offense.

As the date drew near, we spent time discussing dating etiquette. I emphasized the importance of asking her out face-to-face rather than using text messages. We practiced a firm handshake, preparing him to greet her father respectfully. We also talked about being kind and courteous to her mother when he arrived. With every piece of advice, I focused on instilling values of respect, kindness, and chivalry.

On the night of the date, I anticipated a flood of emotions—the heartache of watching him go out with someone other than me. I expected to tear up as I saw him grooming himself with care, catching the scent of the cologne he borrowed from his dad. As his sister playfully teased him about potential kissing and holding hands, I found myself smiling instead of crying.

When Jake appeared in neatly pressed khakis and a well-fitted button-down shirt, I was struck by how much he had grown. I realized I was no longer watching a child but a young man. Yet, I didn’t shed the tears I anticipated. I embraced my role as a parent to a tween, accepting that it was okay for him to pursue his dreams and follow his heart, knowing that a part of me would always be with him.

As I slipped him some extra cash and adjusted his collar, he thanked me for the freedom to go on his date. In that moment, I felt a swell of pride and joy for him, knowing he had found someone who made him feel special. All along, I had been preparing him to let go, and now, I was ready for this new chapter in his life.

However, I reserve the right to unleash my “Mama Bear” instincts should a girl ever break his heart—then all bets are off.

For additional insights on navigating the journey of parenthood and fertility, consider checking out this informative post on couples’ fertility journey. Another great resource for pregnancy information is available at March of Dimes.

In summary, witnessing my son transition into the world of dating has been a profound experience. While the emotions of letting go can be overwhelming, it is heartening to see him follow his heart and chase after happiness, knowing that he carries the values I’ve instilled in him.


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