Uncle Drew recruits a squad of older basketball players to return to the court to compete in a tournament.

Nate Shepherd, late 40's, and Jenny Sparks, early 30's, meet in a fancy New York eatery. Complete strangers who have had a rotten day, waiting for their better halves, they reveal to one another that they are going to meet new people tonight. They quickly realize they are waiting for each other. When Nate loses his girlfriend (after getting fired from his cushy job at an ad agency) and Jenny loses her boyfriend to a drug overdose, Nate's girlfriend suggests that they should move in together as friends to split the rent and ease each others pain. As their friendship grows into something more, their relationship becomes a loving but complicated experience.

When an office full of Chicago real estate salesmen is given the news that all but the top two will be fired at the end of the week, the atmosphere begins to heat up. Shelley Levene, who has a sick daughter, does everything in his power to get better leads from his boss, John Williamson, but to no avail. When his coworker Dave Moss comes up with a plan to steal the leads, things get complicated for the tough-talking salesmen.