In some major American cities, busy and wealthy couples have taken to hiring "mannies"—in part so that their male heirs will have someone to play catch with. "I think that's really good for kids, to have a guy around who's playing rough with them," says Holly Peterson, the author of The Manny, a saucy-socialite novel about the trend. "My son said to the manny the other day, 'I really like it when you beat me up until I'm almost about to cry.' When you're 7 years old, it's exciting to be punched and thrown and make it through and survive. That's what little boys want."

And a contemporary father is not always equipped to provide it. (Anyone who happens to see me trying to throw a spiral or dribble a basketball might think I'm having a seizure.) The stereotype is that men are in the dark about how to talk to their daughters, but for a bookish, gym-averse wuss, there might be no scarier line in the parenting phrasebook than "Hey, Dad, you wanna play catch?"

Then again, that might be just what a frail specimen like me needs. "Boys get close, initially, by doing," says family therapist Steve Biddulph, the author of Raising Boys. "This might mean a father takes on some activities that he doesn't really like. That's what parenthood is about—growing beyond your own preferences. Kids call you out of your comfort zone." With this in mind, I recently bought a miniature basketball and took Toby to a park to shoot hoops. I dribbled, I aimed, and—repeatedly, haplessly, tragically—I missed. And missed. And missed again. I'm not sure whether Toby was laughing with me or at me, but there was something in my drunken-scarecrow form that even a 2-year-old found utterly hysterical. We stayed out there for an hour or so, and when it was over I felt tired, cold, embarrassed, and, yes, strangely elated. Much to my surprise, it was the most fun I'd had in years. My father was never able to make a sports fan out of me, but my son might have better luck.

Does the thought of playing street hockey with your 5-year-old son give you heart palpitations? Talk through your anxieties in the comment section.