Courting Courtney (1997)

On the brink of her 30s, Courtney finds herself in a romantic quandary. Her stagnant relationship with Al is going nowhere, and her dreams of love seem to be slipping through her fingers. Enter Nick, her best friend since high school and a budding documentary filmmaker. In a bid to unravel Courtney's romantic conundrums, he decides to turn his lens towards her life. The film becomes a dynamic exploration of Courtney's world, capturing everything from heart-wrenching breakups to intimate conversations with her old teachers and ex-lovers. Nick's camera doesn't shy away from the raw emotions of Courtney's life, including her desperate quest for love in the face of her looming 30s. From dinner sessions with relatives to encounters with a singles support group, the film paints an honest picture of Courtney's challenges. Her experiments with video-dating and participation in a women's group also make it to the screen, adding layers of complexity to her love life. However, as the documentary unfolds, it becomes evident that the relationship that needs the most exploration is not between Courtney and her romantic partners, but between Courtney and Nick. As Nick continues to delve into Courtney's past and present, he also grapples with his own romantic struggles. His feelings for Courtney, which have been simmering beneath the surface for years, begin to bubble up, leading to a poignant crossroad. Now, they must confront their feelings and decide whether to risk their friendship for a chance at love. "Courting Courtney" is a captivating exploration of love, friendship, and the complexities of human relationships, unraveling the subtle threads that bind hearts and destinies together.

Courting Courtney is a comedy movie featuring Mike Andrews.

It is possible to buy Courting Courtney on Amazon Video.