Freaks and Geeks (1999)

S4E10 Twenty-Five Years Too Late

Walter O'Connor, Kate's first love and now a prominent baseball manager, is visiting the Shady Rest. Kate is thrilled about the reunion but can't shake her nerves about the possibility of a marriage proposal. Meanwhile, Walter's arrival prompts Sam to confront his own feelings for Kate. When Walter ultimately asks Kate to marry him, she surprises everyone by declining the offer, leaving both men to ponder what this means for their futures.