After giving up on making it in the Chicago improv scene, a young comedian fatefully reconnects with the former love of his life one fall night while working at a coffee shop in his hometown. Afraid of growing old and alone like his divorced father, Warren must choose between winning her back or finding the courage to go after his dreams a second time.

Peach Plum Pear is the story of Jesse, a troubled young man from Los Angeles, and his friend Will, who find themselves stranded in small- town Nebraska on their way to Chicago when their car is stolen. The purpose of their trip has a vague connection to Jesse's father, who lives there. During their stay, they work for Hank, a rough and tumble handyman in exchange for his car, who is married to Sharon, the kind bartender who agreed to take them in temporarily. Hank, Sharon, and neighborhood girl Dora, who has strained relationships with the men in her life, teach Jesse surprising lessons about relationships and himself.

When Lucian and his girlfriend Elizabeth arrive at their friend Andrew's isolated mansion to spend the weekend, they discover that Andrew's older sister, Miranda, and her artist boyfriend, Gerald, are already there. Miranda and Gerald quickly upset everyone with their antics, causing Andrew and Elizabeth to retire for the night. Gerald then talks Lucian into a marathon session of alcohol-fueled poker, during which Gerald loses all of his "possessions" to Lucian, including Miranda herself. Miranda and Gerald have a violent argument, and she throws him out of the house. Lucian and Miranda talk late into the night and end up falling asleep in the same bed. Lucian awakens the next day to find that Andrew and Elizabeth have left, leaving him alone in the house with Miranda. Though torn between his devotion to Elizabeth and his attraction to Miranda, Lucian decides to stay at the house for the remainder of the weekend. As the mutual attraction between them grows, so does their unease over ...