Summary: After a picture in the newspaper suggests that Grace is more busted than she really is, she gets a phone call from John Gregorio, a hunk from Grace's high school days, calls up, inviting her to a show of his artwork. Will and Karen both hint that John only phoned because he thinks Grace has big boobs. Grace scoffs at this, but later lets Karen talk her into buying a "hydrabra" to live up to the picture, even though Will insists that she not.

Meanwhile, Jack gets mad at Will when he learns that Will had a fling with Jack's former boyfriend, Walter. Will sees that Jack is really hurt, and tricks him into showing up at the art show so that he can meet Walter, who is now single and wondering about Jack.

At the art show, Grace is loving her new bra. But after snagging the bra on Karen broach, it springs a leak. Will dashes over and informs Grace of her situation while covering her boobs with his hands.

Grace tries to hide the leaks from John, but despite her efforts, she eventually comes clean about the whole thing. John is upset with Grace, saying he would never date someone for the size of their boobs, but for their soul. He then proceeds to hit on Karen, who is bending down to fix her shoe. Grace vengefully sprays John's artwork with her bra.

Later, she admits to Will that he was right. At that time, Walter shows up and Jack forgives Will, then tells him that he was thinking of someone else and runs off.

Did You Notice...
~Karen's comment about "a pack of cigs and a pregnancy scare and this could be high school" is rather reminiscent of Grease, a Broadway show that Megan was in, where the girls smoked and one had a pregnancy scare.
~Another thing about Karen's comment is that she herself had a pregnancy scare in the episode "The Unsinkable Mommy Adler".
~Either Grace gave Jack a key to her apartment or she leaves her door unlocked (though she lives in New York City, so I doubt it). Then again, Jack could have stolen the key, but why would he?
~During this episode, whenever Grace isn't stacked, it's obvious that something was done to her boobs to make them appear smaller than they normally are.
~When this epsiode was repeated on 12/13/2001, John Gregorio's name was mysteriously dubbed to "Donald Dorio" and the name and phone number on the wall were also changed, as well as the closed-caption text. However, Scott Patterson was still credited as "John" in the end credits. The Judy Lombardosi joke about her nick-name, "Slutty Big Boobs", was also cut.
~Submitted by Coreen: I just wanted to point out that in "Das Boob", the man pursuing Grace has a different name every time. Once he was John Greggorio, last night in a repeat he was Don something, and it was different once in the past too. It's written on the wall differently and it's said differently too.
~According to this promo picture, Jack and Karen were supossed to have a scene together in this episode, but it didn't make the final cut.

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