Free food lures Grace to an AA meeting, where she runs into Val. Meanwhile, Jack starts work as a TV executive at a gay network, something which Will is not aware of when he comes to the network for an appointment so he can give suggestions.

When Will and Grace meet a stranger named Ned in the elevator, Grace accuses Will of being too nice to people he doesn't know. While Grace befriends Ned and invites him to dinner, Will makes some nasty remarks about him, but they soon discover that Ned's not the best company to keep. Meanwhile, Jack is having trouble at his new company because he feels he can't relate to his co-workers after they mock him about his Cher doll. Karen and Rosario lend some much-needed support.

Will agrees to fire Karen's pastry chef until the baker cooks up a delectable love triangle for the three of them. Meanwhile, Grace enlists Jack's help in launching boyfriend Nick's career as a television writer but Jack shatters Nick's script-writing dreams.

Having quit his job at the law firm, Will turns to a career in writing where he catches the eye of Malcolm, who claims to have high-profile connections -- but when his writing career fails, Malcolm has another job offer for Will. Meanwhile, Tom, an old flame from college, returns to ask Grace to design a hotel that he and his wife just bought -- only to discover that there are still romantic feelings between the two of them. Jack struggles to produce his latest show for OutTV, but spoiled child star Randall fails to embody Jack's vision. Under threat of a lawsuit, Karen is forced to publicly apologize to Beverly for an embarrassing rumor.

After his first day, Will becomes suspicious of his new job -- especially when he finds himself in an empty office with no co-workers, a German shepherd and a Russian-speaking thug.

Karen feels rattled by Stan's return and Will steps in to help her. Meanwhile Grace is labeled homophobic after her comments on Jack's talk show are misconstrued by gay men from all over New York.

Will and Grace dread a dinner date with married friends Rob and Ellen who likely called the meeting to announce Ellen is pregnant yet again, but when the couple reveals that they are separated and loving it, Grace gets depressed.

After a large corporation takes over OutTV, Jack's talk show "JackTalk" is completely revamped. An immediate change comes when the new conservative owners hire Amber-Louise as "JackTalk's" new co-host.