Kissing a Fool

Jay ends his relationship with Natasha and travels to Milan to write his first book about their relationship. He is melancholic and uses alcohol to cope, signaling the emotional chaos to come. Milan becomes the backdrop for this turning point in his life.

Jay introduces Max to Sam, his editor. After recounting how awful the date was—Sam calling Max a loud drunk, and Max claiming she took him to a strip club—they end up kissing and admitting they fooled Jay. The failed date becomes the spark that pulls them together.

Despite few shared interests, Max and Sam become engaged within two weeks of meeting. They move in together soon after, plunging into a fast-tracked, high-stakes commitment. The wedding plans accelerate this emotional spiral.

A photo of Jay's ex Natasha appears in bridal magazines, unsettling him. He drowns his nerves with a drunken phone call to Natasha. This moment foreshadows the lingering complications around Sam and Natasha.

Max proposes a test: Jay will flirt with Sam and see if she shows any real interest. If she does, Max will feel confident about the marriage. The tension of this test threads through the upcoming events.

A publisher pushes the book's completion date to six weeks, forcing Max and Sam to spend nearly all their time together. Jay becomes more entangled with Sam as the deadline looms. The closeness raises the stakes for everyone involved.

With the dinner nearing, Max travels to Detroit for work while Jay and Sam go out drinking. Jay bumps into Natasha, and Sam pretends she is Jay's fiancée. Natasha seems disheartened by the ruse, adding tension to the love triangle.

Jay crashes at Sam's after a night out, and after finishing his manuscript, Sam talks to him upstairs. Before they can kiss, her cousin Dre interrupts, stopping the moment and leaving them aware of their complicated feelings.

Jay goes to Natasha's hotel room following her invitation; Natasha tries to rekindle things, but he ends up realizing he is finally over her. The encounter clarifies that his feelings have shifted toward Sam.

Feeling guilty about his evolving feelings for Sam, Jay calls Max and reveals that he slept with Dara, the makeup artist. This admission deepens the moral stakes and complicates the friends’ relationships.

Jay rushes to Sam's place to confess, but he chickens out and drinks alone. Max finds him and confronts him about Sam, and they decide to go together to Sam to learn what she truly wants.

Over a meal, Jay declares his love for Sam and kisses her. Max laughs, thinking it's a joke, and reveals the fidelity test he had asked Jay to perform. Sam leaves, breaking ties with both men.

Jay moves to New York City to pursue his next chapter, while Max resolves to reunite Jay and Sam after reading the book he recommended. He begins strategizing how to bring them back together.

While in Chicago for a book signing, Max leaves a note for Jay and enlists Dre to guide Sam to a restaurant. He has notes delivered to both, setting up their meeting in public. The plan hinges on timing and reassurance.

Max gives them his blessing at the wedding, declaring that love cannot be found where it doesn't exist. Jay and Sam dance together, and Max and Linda also dance, signaling a budding relationship between Max and Linda. The film ends with a hopeful note for all involved.