When Cindy Crawford arrives at the KMUP studios, security guard Bobo the Bear develops an instant crush on her and, with a little push from Cupid's arrow, becomes hopelessly smitten. One "60s retro montage fantasy" (and Micky Dolenz cameo) later, Bobo decides to pursue his love. Rizzo tries to coach him, Cyrano de Bergerac-style, but Bobo gets slapped when he mistakenly asks to play with Cindy's balloons. Eventually, though, Bobo gains the courage to tell Cindy that he loves her in his own words and interrupts her duet with Kermit to confess his love.