Setting up play dates for kids can be traumatic

I thought I had it made by marrying my first boyfriend. I never had to worry about prom dates, breakups, make-ups or any of that typical adolescent angst. Most of all, I didn't have to worry about playing the dating game. But then I had kids and realized there's another kind of dating game for parents— one that sneaks up on you with its cute moniker and then viciously rips your heart out: playdating.

My first attempts at playdating began when my kids were in diapers. I went to the park with a bag full of Goldfish crackers and plunked my kids in the sandbox. I'd make light conversation with unnamed mothers and hope to feel a sense of kinship, even though I might never see them again. My children were not particular about their companions, and were content to be with whoever had the best shovel and pail.

But I wasn't good at "flirting" with the other mommies, winning them over with witty banter or interesting stories. Quiet and introverted, I felt like a tag-along. To make things worse, I was often out of my league when conversations turned to second pregnancies, issues of labor and delivery, and breast-feeding because my children were adopted.

When my oldest child entered preschool, another social opportunity arose. Almost immediately I was invited on playdates. The experience was awkward. I would arrive at a stranger's house, or she would come to mine, and we would sit together and make stilted conversation while our children entertained themselves with whatever toys we made available. After a few hours, we would separate. I was always left with an empty feeling, and a burning desire to ask: "Did you like me? Do you want to go out again?" Playdates in preschool were more about parent compatibility than anything else. If we didn't get a second invitation to play, I felt like I had been dumped.

But I persevered. By the time my son was in kindergarten, I was making phone calls and attempting to pencil things in on the calendar. Nonetheless, calls to our house were few and far between. I wondered if my son's empty social calendar was my fault: Were the other mothers rejecting me? Or were the other children rejecting my son? I made a few calls, but people always seemed to be busy with skating lessons, soccer practice, karate.

Past generations had the luxury of taking the essential childhood experience of playing for granted. When I was growing up, the streets filled with kids riding bikes, playing "graveyard tag" in the twilight hours, and just bopping around from one house to another. On a snow day, kids would convene in my backyard where my dad maintained a toboggan run, complete with benches, jumps and my mother's never-ending supply of cocoa. In the summer, hordes of children gathered for spontaneous water-balloon battles. There was no such thing as a playdate.

Today when we have a snow day, my kids sled down our front hill by themselves. Front yards are empty and the street is quiet except for the occasional laugh of a child cavorting in his own backyard.

It seems that we are up against a rising tide of scheduled childhoods born from a culture of fear. No one I know allows her young child to explore the woods, wander local neighborhoods or ride a bike across town without supervision. Children can't play in their own front yards without parents' sitting on guard at the window. We have come to accept that it is our job to keep our children from harm at the expense of everything else.

Because of this, parents can no longer count on the spontaneity and curiosity of childhood to bring children together for social interaction. Instead, we schedule them in sports and dance and after-school programs where other adults set limits and structure the time. It seems we are all running in different directions, looking to come together, but flailing alone on the fringes.

Thus we find ourselves playing the dating game. You charm, you negotiate, you compare and you settle. I don't try as hard as I used to. In many ways, I am selfishly hanging on to the last few moments when my son will want to be with me; all too soon the time will come when "Mom = uncool." And yet … I've made a strategic move in the dating game: I've decided to play hard to get.

A few weeks ago I got an e-mail from the mother of one of my son's friends: "Hey! We haven't seen you guys in a long time. How about a playdate on Saturday?" I think this new approach is working.