Hank is dismayed when he sees the film version of his acclaimed novel, agrees to a blind date arranged by his agent, and learns that his ex-girlfriend Karen is engaged to another man. Series premiere.
Hank reluctantly accepts a blogger gig for a hip L.A. web site, and endures a dinner party with Karen and her finance Bill that yields a scandalous romp with a sexy Scientologist.
Hank ponders whether to continue his blogging job after he discovers the identity of the web site's owner, and reconnects with Meredith, his one-time blind-date disaster; Charlie's relationship with his assistant takes a surprising turn.
The fiercely apolitical Hank is dragged to an environmental fundraiser at Charlie's agency, where he briefly displays his gallant side to both Meredith and Karen, and inadvertently discovers his agent's dirty little assistant secret.
A point of modern linguistic style comes between Meredith and Hank, who also guest-lectures Mia's creative writing class; Becca and Karen both crush on a cool guitar teacher but Mia breaks both their hearts.
Becca's impressive musical performance at a rock concert leads to a romantic, booze-fueled moment for Hank and Karen, but it doesn't last; Charlie's dalliance with his assistant is nearly discovered by Marcy.
Hank makes peace with his archenemy Todd and lands Karen a designing gig, but a dilemma with Mia interrupts their temporary bliss; Charlie attempts a disastrous threesome with his wife and assistant.
Hank receives bad news about his father and embarks on a grief-stricken bender of booze, drugs and even a prostitute as he remembers the last time they saw each other.
A manuscript for a new novel and a royalty check from his movie inspire Hank to go on a spending spree, but his purchases don't have the desired effect on his life; Marcy drops a bombshell on Charlie.
A creative meeting about a gig writing a female boxing movie turns into a mini-orgy for Hank and his new "roommate" Charlie, but their ecstasy soon turns to agony; Dani and Mia have a creative meeting of their own.
Bombshells drop on all fronts: Hank discovers Mia is peddling his book as her own, and she threatens to reveal their one-night stand if he reclaims his work; Becca tells Karen she wants to go live with her father.
The wedding of Karen and Bill provides the impetus for emotional revelations that threaten to derail the entire ceremony unless Hank can put everything right. Season finale.