Gus invites a diverse group of guests to his birthday party, including Calvin, who plays Nicholas — a 36-year-old actor with an unconventional view on relationships, believing that there is no such thing as bad sex. Among the attendees is Francesca, a 33-year-old movie star, completely oblivious to her considerable wealth. Other notable guests include Lee, a 41-year-old executive portrayed by Catherine Keener, who falsely believes she was personally invited by Gus, and her husband Carl, played by [David Hyde Pierce], a 42-year-old screenwriter struggling with feelings of inadequacy as he worries about being perceived as boring by his wife.
As tensions rise, we find Lee's sister, Linda (Mary McCormack), joining the festivities, hoping to find romance, as Lee secretly aims to set her up with Gus. Linda longs for affection, while Carl, despite loving Lee, feels the strain in their relationship due to her indifference. Meanwhile, Calvin, through the guise of Nicholas, finds himself unexpectedly enamored with Francesca, who’s cunningly posed as a journalist for an interview. In a world of confusion and misplaced identities, Francesca discovers genuine love amid her charade.
Carl, plagued by unsettling dreams that bleed into his waking hours, faces the harsh reality of losing his job as he's released from his duties at a magazine focused on the darker aspects of life. After a troubling revelation at home involving his dog, he connects with the veterinarian and finds fleeting solace in their honest conversation over shared brownies laced with marijuana.
On the work front, Lee is emotionally volatile, aiming to sever ties with Carl in her own explosive manner, while also dealing with the firing of several employees. Her anger surfaces when she learns of Calvin's infidelity, only exacerbated during a lunch with Linda where she criticizes last year's birthday gift but is left speechless by Linda’s present this year: a simple coin purse.
In the background of this chaos, Arty (Enrico Colantoni) tries to balance his directorial duties for a play amidst his rising tensions with a domineering actor embodying Hitler. As personal and professional lives intertwine, unexpected developments occur when Linda, now employed at a hotel, connects with Gus while providing him a massage. As she prepares to meet a man she believes to be an ideal partner, the reality of his actual identity threatens to shatter her dreams.
Meanwhile, the film within this narrative reaches its climax, with Francesca interviewing a conflicted Nicholas about the representation of African Americans in Hollywood. As their on-screen chemistry intensifies, it spills over into real-life emotions, culminating in compelling moments of connection and misunderstanding.
At the ill-fated party, as emotions intertwine and tensions peak, a tragic turn of events unfolds when Linda discovers Gus’s lifeless body. This shocking revelation beckons Lee back to Carl, sparking the hope for reconciliation. And as the sun rises on a new day, the characters must confront their realities and the impact of their choices amidst the whirlwind of relationships and desires.
