Kissing a Fool
May the best man win.
1998 · 93 min · ★ 5.5 · Comedy, Romance
An egotistical television personality enlists the assistance of his best friend in putting the fidelity of his fiancé to the test in this amiable comedy of the sexes. Told in flashback, the film takes a familiar love-triangle scenario and gives it a bitter twist. With a bride who seems too good for either suitor, the film is sustained by one question - who will she choose?
Directed by Doug Ellin · Written by James Frey
Your Rating
Where to Watch
Rent or Buy
Cast
-
David Schwimmer Max Abbitt -
Jason Lee Jay Murphy -
Mili Avital Samantha Andrews -
Bonnie Hunt Linda Streicher -
Vanessa Angel Natasha -
Judy Greer Andrea -
Kari Wührer Dara -
Frank Medrano Cliff Randal -
Bitty Schram Vicki Pelam -
Jerry Springer Self -
Sammy Sosa Self -
Liza Cruzat Dara's Friend #1
More from Doug EllinSee all →
The Power of Pickleball · 2026The Power of Pickleball
★ 9.02026
MovieDocumentary
"The Power of Pickleball" tells the story of a humble game that spread into a cultural phenomenon by bringing people together across generations, backgrounds, and walks of life. Centered on the passionate individuals who helped build the sport from the ground up, the film celebrates pickleball's unique ability to create community, spark joy, and change lives in unexpected ways.
Entourage · 2004Entourage
★ 7.42004
SeriesComedyDrama
Film star Vince Chase navigates the vapid terrain of Los Angeles with a close circle of friends and his trusty agent.
Nash · 2013Nash
★ 6.52013
MovieDocumentary
This coming of age documentary chronicles the life of NBA All Star Steve Nash as he tries to navigate his way through the somewhat toils of professional sports while trying to leave a lasting legacy on and off the court.
Entourage · 2015Entourage
★ 6.22015
MovieComedyDrama
Movie star Vincent Chase, together with his boys, Eric, Turtle and Johnny, are back…and back in business with super agent-turned-studio head Ari Gold. Some of their ambitions have changed, but the bond between them remains strong as they navigate the capricious and often cutthroat world of Hollywood.
Bull Run · 2025Bull Run
★ 5.72025
MovieComedy
Follows Bobby Sanders, an ex-pro-hockey-player-turned-junior-banker as he navigates the peculiar and somewhat surreal world of high finance and faces life's meaning within this gilded cage.
Bad Santa 2 · 2016Bad Santa 2
★ 5.42016
MovieComedyCrime
Fueled by cheap whiskey, greed and hatred, Willie Soke teams up with his angry little sidekick, Marcus, to knock off a Chicago charity on Christmas Eve. Along for the ride is chubby and cheery Thurman Merman, a 250-pound ray of sunshine who brings out Willie's sliver of humanity. Issues arise when the pair are joined by Willie's horror story of a mother, who raises the bar for the gang's ambitions, while somehow lowering the standards of criminal behavior.
Phat Beach · 1996Phat Beach
★ 5.21996
MovieComedyDrama
A hefty homeboy borrows his dad's Mercedes and goes to the beach with his friends for wild sun & fun.
Erotic Confessions: Volume 1 · 1996Erotic Confessions: Volume 1
★ 4.31996
MovieRomance
Erotic Confessions: Volume 1 Episodes: Midnight Showing; The Business Trip; The Painting
More Like This
Bull Durham · 1988Bull Durham
★ 6.61988
MovieComedyRomance
Veteran catcher Crash Davis is brought to the minor league Durham Bulls to help their up and coming pitching prospect, "Nuke" Laloosh. Their relationship gets off to a rocky start and is further complicated when baseball groupie Annie Savoy sets her sights on the two men.
Casablanca · 1943Casablanca
★ 8.11943
MovieDramaRomance
In Casablanca, Morocco in December 1941, a cynical American expatriate meets a former lover, with unforeseen complications.
Contempt · 1963Contempt
★ 7.01963
MovieDramaRomance
Art film producer Jeremy Prokosch, unhappy with the work of his director, hires Fritz Lang (as himself) to direct an adaptation of The Odyssey, but when it seems that the legendary filmmaker is making a picture destined to bomb, he brings in a screenwriter to energise the script. The professional intersects with the personal when a rift develops between the writer and his wife.
You Choose! · 2017You Choose!
★ 5.72017
MovieRomanceComedy
Even at the age of 40, Juliette is used to other people making decisions for her. When she meets two guys she likes, she has to finally make her own decision.
French Kiss · 1995French Kiss
★ 6.51995
MovieComedyRomance
After her fiancee admits to infidelity while on a business trip in France, a woman attempts to get her lover back and marry him by traveling to Paris despite her crippling fear of flying. On the way she unwittingly smuggles something of value that has a charming crook chasing her across France as she chases after her future husband.
Sissi · 1955Sissi
★ 7.31955
MovieComedyDrama
The young Bavarian princess Elisabeth, who all call Sissi, goes with her mother and older sister Néné to Austria where Néné will be wed to an emperor named Franz Joseph, Yet unexpectedly Franz runs into Sissi while out fishing and they fall in love.
Notorious · 1946Notorious
★ 7.71946
MovieRomanceMystery
In order to help bring Nazis to justice, U.S. government agent T.R. Devlin recruits Alicia Huberman, the American daughter of a convicted German war criminal, as a spy. As they begin to fall for one another, Alicia is instructed to win the affections of Alexander Sebastian, a Nazi hiding out in Brazil. When Sebastian becomes serious about his relationship with Alicia, the stakes get higher, and Devlin must watch her slip further undercover.
Brief Encounter · 1945Brief Encounter
★ 7.71945
MovieDramaRomance
Returning home from a shopping trip to a nearby town, bored suburban housewife Laura Jesson is thrown by happenstance into an acquaintance with virtuous doctor Alec Harvey. Their casual friendship soon develops during their weekly visits into something more emotionally fulfilling than either expected, and they must wrestle with the potential havoc their deepening relationship would have on their lives and the lives of those they love.
Sleepless in Seattle · 1993Sleepless in Seattle
★ 6.71993
MovieComedyDrama
After the death of his mother, a young boy calls a radio station in an attempt to set his father up on a date. Across the country, an engaged woman becomes convinced that they belong together, despite their never having met. Will their paths collide despite the odds?
Dangerous Liaisons · 1988Dangerous Liaisons
★ 7.21988
MovieDramaRomance
In 18th century France, Marquise de Merteuil asks her ex-lover Vicomte de Valmont to seduce the future wife of another ex-lover of hers in return for one last night with her. Yet things don’t go as planned.
Doctor Zhivago · 1965Doctor Zhivago
★ 7.61965
MovieDramaRomance
The life of a Russian physician and poet who, although married to another, falls in love with a political activist's wife and experiences hardship during World War I and then the October Revolution.
The Magnificent Ambersons · 1942The Magnificent Ambersons
★ 7.31942
MovieDramaRomance
The spoiled young heir to the decaying Amberson fortune comes between his widowed mother and the man she has always loved.
The Front Page · 1974The Front Page
★ 7.31974
MovieComedy
Ruthless Chicago newspaper editor Walter Burns resorts to dubious motives in order to get top reporter Hildy Johnson to cover one more big crime story before retirement.
Kolya · 1996Kolya
★ 7.31996
MovieDramaComedy
After a fictitious marriage with a Russian emigrant, Cellisten Louka, a Czech man, must suddenly take responsibility for her son. However, it’s not long before the communication barrier is broken between the two new family members.
Mr. & Mrs. Smith · 2005Mr. & Mrs. Smith
★ 6.72005
MovieActionComedy
A husband and wife struggle to keep their marriage alive until they realize they are both secretly working as assassins. Now, their respective assignments require them to kill each other.
The Flintstones · 1994The Flintstones
★ 5.41994
MovieFantasyComedy
Modern Stone Age family the Flintstones hit the big screen in this live-action version of the classic cartoon. Fred helps Barney adopt a child. Barney sees an opportunity to repay him when Slate Mining tests its employees to find a new executive. But no good deed goes unpunished.
