Das Boob

S2, E3: When a photo of Grace (Debra Messing) gets published in a newspaper in which she appears to be much more well-endowed than she actually is, she gets asked out the next day by her unrequited high-school heartthrob (guest star Salvator Xuereb), but Karen (Megan Mullally) convinces her it's only because of the photo. Desperate to live up to her "fullfigured" image, Grace buys herself an undergarment that has less than the desired effect. Meanwhile, Jack (Sean Hayes) discovers that Will (Eric McCormack) slept with one of his old lovers.