Movies like Kissing a Fool

He's Just Not That Into You intertwines various stories of men and women attempting to navigate their romantic lives, dealing with issues of attraction, commitment, and misreading signals. The multi-narrative structure and focus on the difficulties of modern relationships mirror the tangled romance in Kissing a Fool and make it a relevant recommendation.

Chasing Amy centers around a comic book artist who falls in love with a woman, only to find out she does not share his sexual orientation. The film's witty banter and exploration of unconventional relationships offer a smart and sensitive approach to themes of love and friendship that might resonate with fans of Kissing a Fool.

The Break-Up takes a comedic look at the end of a relationship between two strong-willed personalities, offering a blend of humor and heartache that resonates with the romantic turmoil found in Kissing a Fool. The film's setting in Chicago and the involvement of complex love dynamics make it ripe for viewers who appreciated the themes and setting of Kissing a Fool.

The Object of My Affection follows a woman who falls for a man who happens to be gay; the two form an unconventional relationship that tests the boundaries of love and friendship. The film's exploration of the complications that arise when friendship blurs into romance will strike a chord with those who enjoyed the fluid relationships depicted in Kissing a Fool.

The Truth About Cats & Dogs is a romantic comedy that delves into themes of self-esteem and the perception of beauty within the scope of love -- themes that fans of Kissing a Fool will likely appreciate. Its engaging storyline and endearing characters create a charming concoction of love and laughter.

Playing for Keeps tells the story of a charming, down-on-his-luck former sports star who finds himself coaching his son's soccer team and trying to put his life back together. The romantic and comedic elements, along with the protagonist's journey of self-discovery, parallel the themes of love and career ambitions present in Kissing a Fool.