Lucy Neal is thrown for a loop when she is accused of being too inhibited by her ex-boyfriend. In an effort to prove him wrong, Lucy creates a rather wild to-do list that sends her on a whirlwind and surprising journey of self-discovery, friendship, and new love.

Kabir is a lonely medical student in New York, estranged from his wife and grieving the loss of his mother. When he meets Kioni, a charming film student from Kenya, she persuades him to show her the city's Christmas decorations, thereby leading him to rediscover the magic of the holiday season and get his life back on track.

Nick comes to New York to temporarily live with a jazz musician friend of his late father's named Cal while his mom is in rehab. During his time in the city, he befriends a group of kids who show him what New York has to offer.

Sara is in crisis. Engaged for one day, she decides to call off her marriage. Quirky, beautiful, and tender, she is working on being bold. Having had a short relationship with a woman in college, Sara seeks that feeling again. How can she have a woman’s touch without giving up men entirely? This question launches Sara on a bittersweet journey filled with self discovery, sexual awakening, beautiful women and sometimes men.

The story of the legalization and subsequent rise of the porn industry in New York’s Times Square from the early ’70s through the mid ’80s, exploring the rough-and-tumble world that existed there until the rise of HIV, the violence of the cocaine epidemic and the renewed real estate market ended the bawdy turbulence of the area.