You're an involved and attuned Dad who's provided top-notch schooling and limited-edition footwear. Your kids are smart and discerning, sneering at the Jonas Brothers and revering Johnny Cash. You couldn't be prouder, really. Until one day that parental pride takes a dark turn. It hits you suddenly, while you're driving carpool to surf camp or getting your ass handed to you in a Super Mario Galaxy matchup or watching your son IM with six girls simultaneously: You're jealous.

And, let's be honest, there's plenty to begrudge. Not only do your kids have a far sweeter setup than you had growing up—in the days when Atari ruled and easily accessible porn meant your sister's Judy Blume collection—but they also have it better than you do now. While you spend your after-work hours comparing tax-sheltered college funds and negotiating the Byzantine politics of private-school admissions, your progeny feast on a smorgasbord of awesome social, educational, and entertainment options. Your kids have multiplayer online games and the time to play them. They know the difference between sushi and sashimi, and they get the benefits of ordering omakase. Junior—God bless him—keeps getting smarter and savvier; he's effortlessly cool and young while you struggle to hang on, wincing from an Achilles tendon strained playing H-O-R-S-E and fighting the urge to sing along with "I Kissed a Girl" in your Passat wagon.

"It doesn't make much sense, but yeah, there's definitely envy," says Jason Avant, 40, founder and managing editor of the blog Dadcentric.com. A father of two in Encinitas, California, Avant has watched his 5-year-old, Lucas, become a badass in karate—which is all well and fine, except that Dad can't quite let go of the fact that he was once pretty good at martial arts himself. "I'm watching him getting better and better and realizing I'll never have that chance," Avant says. "It sounds silly, but I'm suddenly aware that I'll never be in 5-year-old shape again."

That may be the most common strain of paternal jealousy. Just as many mothers resent their daughters as they begin to fill out and attract sidelong glances, fathers are often hit with pangs of regret when their sons come into their own physically. Consider those all-too-intense Pony League dads, whose joy at watching their boys scramble around in pro gear is overwhelmed by the ache to suit up themselves. That paternal conflict is writ large in Friday Night Lights and the real-life case of Archie Manning—who exudes alpha-male pride at having sired three star football sons but can't help but betray a certain envy over Peyton's and Eli's Super Bowl successes.

Beyond athletics, many dads envy the sheer diversity of options and opportunities their offspring have. Whit Honea, the blogger behind Honea Express and the father of a 6-year-old, Atticus, and a 3-year-old, Zane, recently moved to a family-friendly community near Seattle that offers children's yoga and glassblowing. Glassblowing, Daddy! "These kids are like little artisans," he says. "Here they are living a life of arts and leisure, and I'm living a life of grindstone and stress."