Andrew Rosenbach

In a sneaky ploy to bum a night off from work at Barney's department store, a conniving Jack plays matchmaker and takes advantage of his geeky female supervisor's (guest star Parker Posey, "Best In Show") interest in Will (Eric McCormack) - while mindful of Will's fantasy of modeling in the store's catalogue - and he parlays their mutual desires into a "date," even though his unsuspecting friend doesn't have a clue of her intentions. Elsewhere, Grace (Debra Messing) goes where no woman should when she compares her previous sexual experience with her boyfriend Nathan's (Emmy Award-winning guest star Woody Harrelson, "Cheers"). Megan Mullally also stars.

After Will (Eric McCormack) and Grace (Debra Messing) decide to have a baby together, obstacles pile up, including a missing specimen sample and bungled insemination efforts that have them teetering between artificial and natural means - all leading to mis-conceptions. Meanwhile, Jack (Sean Hayes) considers giving up his show-business aspirations, until he gets some career advice from an unexpected source - his idol, Cher (guest starring as herself). Likewise, married Karen (Megan Mullally) is sorely tempted by the romantic tickling of a rich and natty gentleman (guest star Rip Torn, "Men in Black"). Shelley Morrison also stars. Part 1 of 2.