Nate & Margaret

Nate, a young film student, and Margaret, a middle-aged aspiring comedian, have a unique and quirky friendship that is put to the test when Nate starts dating James, a charming but selfish classmate. As Nate becomes more focused on his new relationship, he begins to neglect his friendship with Margaret, who is struggling to start her career as a stand-up comedian. When Nate's apartment is burglarized and he loses all his possessions, he lashes out at Margaret, leading to a rift in their friendship. The two go their separate ways, but eventually find their way back to each other and rekindle their friendship.

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Some movies that have similar genres and were produced around the same time as Nate & Margaret include Delivery Man, How to Be a Latin Lover, The Intern, Hello Kitty Flanagan, Dirty Grandpa, American Pie Presents: The Book of Love.