When Grace convinces Karen to accompany her to her father Martin's birthday bash, the situation turns awkward when it is just the three of them. Struggling to gain the attention of her seemingly aloof father, Grace tags along with him to the golf range in hopes of scoring some quality bonding time. Meanwhile, Karen keeps herself entertained with Martin's buddy, Burt Wolfe. Excited about the date that Jack has arranged for him, Will discovers the true meaning of the phrase "blind date.".

Having quit his job at the law firm, Will turns to a career in writing where he catches the eye of Malcolm, who claims he has 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 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, but Karen has a different announcement in mind.