Kissing a Fool (1998)

Best friends since they were kids, Rabbi Jacob Schram and Father Brian Finn are dynamic and popular young men living and working on New York's Upper West Side. When Anna Reilly, once their childhood friend and now grown into a beautiful corporate executive, suddenly returns to the city, she reenters Jake and Brian's lives and hearts with a vengeance. Sparks fly and an unusual and complicated love triangle ensues.

On the set of a playwright's new project, a love triangle forms between his wife, her ex-lover, and the call girl-turned-actress cast in the production.

On the eve of his wedding to his longtime girlfriend, unassuming nice guy Rick is dragged out for a night of debauchery by his friends.

When she receives word that her longtime platonic pal Michael O'Neal is getting married to debutante Kimberly Wallace, food critic Julianne Potter realizes her true feelings for Michael -- and sets out to sabotage the wedding.

Tom and Hannah have been platonic friends for 10 years. He's a serial dater, while she wants marriage but hasn't found Mr. Right. Just as Tom is starting to think that he is relationship material after all, Hannah gets engaged. When she asks Tom to be her 'maid' of honor, he reluctantly agrees just so he can attempt to stop the wedding and woo her.

A washed up golf pro working at a driving range tries to qualify for the US Open in order to win the heart of his succesful rival's girlfriend.

Miles Harding buys a state-of-the-art computer that starts expressing conscious thought and emotion after an interaction with spilled champagne. Things begin getting out of hand when both Miles and Edgar, the computer, fall in love with beautiful neighbor Madeline Robistat.

Celebrity photographer Connor Mead lives life in the fast lane, committed to lifelong bachelorhood and simultaneous relationships with multiple women. On the eve of his younger brother Paul's wedding, Connor's mockery of love proves a real buzz-kill for everyone - including his childhood crush, Jenny, the one woman who always seemed immune to his considerable charms. Later that night, he gets a wake-up call from the ghost of his late Uncle Wayne, the hard-partying, legendary ladies' man who was Connor's mentor. Uncle Wayne has an urgent message which he delivers through three ghosts who guide Connor on an eye-opening tour of his romantic past, present and future. Along the way, they attempt to discern whether he will ever be able to change his ways -- and if there is any hope of him finding true love.

Brucey, the son of Oscar, calls his father to invite him to his wedding to Felix's daughter next Sunday in California. Oscar and Felix meet again at Los Angeles International Airport and rent a car in order to go to San Malina for the wedding.

It's prom season, and high school senior Mandy and her best friend and fellow outsider Ben are surrounded by over-the-top "promposals." Mandy is only focused on getting into her dream school Harvard, but as she starts tutoring basketball all-star Graham, she must re-evaluate whether her dream school is worth the cost of everything she believes in.