|Original Airdate||January 16, 1998|
|Written by||Jeff Menell|
|Directed by||Lisa Gottlieb|
|Guest starring||Tico Wells as DJ Johnny Latte, Mindy Spence as Jill, Caroline Keenan as Carol, Greg Collins as Freezing Guy, Glen Chin as Eskimo, Max Miller as Bobby, Matt Kirkwood as Lunatic|
Upset by their lack of effort, Mr. Feeny assigns impossible assignments to Cory, Topanga, and Shawn. He assigns Shawn to get Superbowl tickets, Topanga to butt out of it, and Cory to help them both succeed or he fails. Unjust as it seems, the three go off to accomplish their tasks. Topanga manages to get Cory & Shawn's attention to a radio contest to win Superbowl tickets, but it requires Shawn waiting atop a billboard longer than everyone else. Unfortunately, the final contestant is an Eskimo (eating an ice cream cone), and Shawn admits defeat.
Convinced they've figured out Feeny's meeting, they confront him telling him that they've learned that they should still try, even if it seems like what they're doing is pointless. Feeny, still upset, insists that Shawn needs Superbowl tickets, Topanga must butt out, and Cory must help the both. This sends Shawn into a spiral, where he realizes that there will always be an Eskimo (metaphor for an obstacle) standing in his way. He goes to San Diego to the Superbowl without tickets, and Cory steps aside and lets him.
Pleased, Feeny tells them that was his lesson. Shawn must learn to do things things on his own and Cory needs to learn to let Shawn do things on his own. Topanga needs to learn that being perfect isn't always the most important thing: helping your friends is. As they watch the Superbowl at Chubbie's, Feeny excitedly points to the screen, for he sees Shawn holding a sign in the stands.
Meanwhile, in their search for perfect soulmates, Jack and Eric end up with girlfriends just who are just like each other. Noticing this, Jack and Eric attempt to switch them, but when they notice, they point out that being with someone just like them would be boring and they storm out. Now alone, Jack and Eric agree that they should just wait for their soulmates to find them. Outside, Jill and Carol (the dates) wait impatiently, in disbelief that Jack and Eric wouldn't pursue them.