Will & Grace
Will Truman and Grace Adler are best friends living in New York, and when Grace's engagement falls apart, she moves in with Will. Together, along with their friends, they go through the trials of dating, sex, relationships and their careers, butting heads at times but ultimately supporting one another while exchanging plenty of witty banter along the way.

Season 3 · Episode 21 ·
The Young and the Tactless
Grace gives romantic advice to her slovenly new neighbor, Nathan, in hope of reuniting him with his girlfriend so he will move away. Meanwhile, Will and Jack are out on the town with an unwelcome chaperone: Karen's oblivious mother-in-law.
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Episode 21 of season 3 of Will & Grace: “The Young and the Tactless”. Aired 2001-04-26. Watch it online free on ZapFlix.