Stuart's longtime girlfriend is off to Portland on a two month work assignment. Before she leaves, she gives him an ultimatum -- prove to her that life in Chicago is worth coming back for, or buy an enagagement ring and get his butt up to Portland, too. What starts out as a worry-free, bachelor summer for Stuart, of whiffleball and partying with the guys, turns into the rite of dreaded 'maturity' instead. Stuart ultimately learns 'growing up' isn't about making predictable decisions, it's about finding out who you really are. After all, change begins at home plate.