Will & Grace: Season 10, Episode 4

10 - 4: Who's Sorry Now?

Will and Grace discover old letters written to each other from their college days, and decide to read them together. But reminiscing about the past turns ugly when a major bombshell is revealed in one of the letters. Meanwhile, when Karen announces she'll never fall in love again, Jack channels Rosario - or does he? - to convince her it's never too late to find love