Jenn first appears in a jail in Milwaukee bailing out the character from jail, assuming the character can either be Jim McMahon, Walter Payton, or William Perry. The character than asks her if he could get a plane ticket back to Chicago. She responds that she has a ticket, but she'd only give it to him if he can do some favors. During the favors, she develops a strong friendship for the character. Once the character finishes the favors, she says she will show up to some of his games, and she gives him the ticket to Chicago. She appears at one of the characters games against the Detroit Lions and asks the character for the tape. She quickly sneaks into the Silverdomes control room and plays the VHS tape on the stadiums video screen. Eventually busting Coach Darryl Rogers for drunk driving. The game was cancelled and she returns to the character with the tape. The character thanks Jenn for her help and she felt flattered. She once again appears on the telephone with the character about going to the Super Bowl if the Bears win the championship, earning a sideline ticket to Super Bowl XX. She once again appears at Super Bowl XX with the character and tells him that she hopes they win cause shes got a suprise too. Once the character has won the Super Bowl, the character is then joined with Jenn on mid field telling him that he really played a great game. The character than reponds with what the suprise was. Jenn finally wraps her arms around the character and kisses him and presumably fall in love.