Twenty-Five Years Too Late - S4.E10

Kate's first boyfriend, Walter O'Connor, who is now a major league baseball manager, is coming to stay at the Shady Rest. While Kate is excited to see Walter, she is still just as anxious and nervous about him actually asking her to marry him. Regardless of Walter's intentions, his being there makes Sam come to the realization that he too has feelings for Kate. Walter proposes to Kate, but she turns him down.