Kissing a Fool

Set in the late 1990s, the movie centers on contemporary dating, publishing deadlines, and urban social life. Characters juggle careers and romance against sleek city backdrops and casual nightlife, reflecting the era’s blend of humor and heart. The pace and pop culture references echo the era's sensibilities toward love and commitment.

The story traverses major urban centers—from Chicago, the hometown of Max and Jay, to Milan where Jay writes about their relationship, and on to Detroit and New York City for work and romance. The film uses these cities’ nightlife, hotels, and dating scenes to explore modern relationships. The cityscapes serve as a backdrop for fast-paced dating, misunderstandings, and life-changing choices.

💘 Romance

Romance drives the plot as Sam and Jay navigate growing feelings amid a chaotic web of friends, exes, and loyalties. The film probes what fidelity means when attraction and affection collide with friendship. It also questions whether true love can survive tests and misunderstandings.

🧭 Trust & Loyalty

A playful yet pointed examination of trust, where a ‘fidelity test’ is used to measure commitment. The characters learn that manipulation undermines genuine connection, while honesty ultimately proves more rewarding. The narrative shows loyalty built on openness rather than games.

🎭 Friendship & Comedy

Friendship underpins the romance, as Max and Jay’s long-running bond provides both support and friction. The film uses humor, mistaken motivations, and witty banter to light up serious relationship questions. The comedic tone keeps the moral reflections accessible and entertaining.