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 2 · Episode 3 ·
Das Boob
A deceiving, but flattering, newspaper photo makes Grace look more "endowed" than she really is and gains her the attention of a former high school heartthrob who was never one to keep abreast of her before. Jack is destroyed to learn that Will had a fling with Walter, Jack's ex-boyfriend.
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Episode 3 of season 2 of Will & Grace: “Das Boob”. Aired 1999-11-02. Watch it online free on ZapFlix.