The Playdating Game: Finding the Perfect Playdate Match


I did not enjoy dating. Bad first dates haunted me: the verbal missteps, the physical discomfort, the endless overanalysis. It was a happy day when marriage promised — among other things — the end of such experiences.

Then we had children. I was not yet done with the dating game.    

Enter playdating, the potentially terrifying yet necessary socialization of parents and children. The terror comes from the fact that not only must you match personality and disposition with another caretaker, but also between children. Even would struggle to successfully pair the mood swings, snack attacks, and territorial aggressions of two toddlers.  

As a teacher, I’d had the blessing of daycare providing some of this daily socialization, and summers off with co-workers raising similarly aged children. The playdates happened naturally, comfortably, peppered with goldfish crackers and authentic conversation.

Then I left my job after baby number two. We still had our summertime playmates, but the winters became long, cold, and lonely. I had no inner circle of confidantes with stay-home schedules, and it was unclear how to enter the world of other caretakers who were already blissfully matched.  

The three of us visited libraries, indoor play opportunities, music classes, and area museums, and we would interact successfully as we met with others our age. But how do you move it to the next level? At what point is it OK to say “So, uh, I don’t know … can I have your number?” I would leave these gatherings feeling steeped in failure if I hadn’t secured the contact information of my — or my child’s — new best friend.  

When my now-4-year-old started school, I cheered, reminded that this world was my happy place, comfortable and familiar. This is where we would meet the friends and families we’d cherish for the next 20 years.

The magic didn’t happen immediately.  Small talk was readily available as we dropped off and retrieved our tired darlings, but I was many times consumed with the same first-date jitters. The missteps, the discomfort, the overanalysis…they all came roaring back.

Is it oversharing if I describe in graphic detail our weekend bout with the stomach flu? Too soon to express my occasional doubt about leaving the workplace? Does anybody want to guess how many days I can go without washing my hair? “Our place or yours?” never seemed to be in the conversation’s natural progression.

I had been reduced to an angsty teen with middle-aged eye bags. How had this happened?

Perhaps my vision of brief, chaotic drop-offs and pick-ups as networking happy hours was problematic. Maybe my desperation for new connections was too pungent for my busy and justifiably oblivious fellow parents. It’s possible I expected too much.  

At long last, and many months into the school year, my son directed the decision. He found a good friend in class whose mom passed me her card in invitation for a playdate. And that was it. Weeks of kicking myself for not being proactive and asking anyone out faded away in the bright dawn of being pursued. We had a match.

After finding the rhythm of those first playdating decisions — organic, gluten-free snacks or sugar-saturated junk food? — it became easier to initiate playdates with other new friends and the pressure subsided. I’m no longer out to find lifelong companions, but interesting and fun friends who enrich our lives and benefit equally from the relationship.

No doubt my dating misadventures might’ve been more enjoyable had I kept a similar perspective.

So why put up with the playdating anxiety? Because kids love the play, parents need the adult affirmation, and even bad dates make good stories.

Do you have playdate anxiety? 


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