Movies Like Kissing a Fool (1998)

Kissing a Fool is a 1998 comedy, romance film from Doug Ellin with a MovieMagicScore of 5.5/10. Here are 20 similar films, ranked by real viewer ratings — starting with The Manxman and Sleep with Me.

Comedy Romance

The Manxman

1929

A fisherman and a rising lawyer who grew up together as brothers fall in love with the same woman.

6.1

MagicScore

Sleep with Me

1994

Six different writers wrote a scene each of this romantic comedy featuring the marriage and turbulent relationship of Joseph and Sarah, with Joseph's best friend Frank trying hard to cope with letting the love of his life marry his best friend.

5.7

MagicScore

The Groomsmen

2006

Blue-collar Paulie prepares for fatherhood and his forthcoming wedding to Sue by hanging out with his groomsmen. Brother Jimbo, cousin Mike, and his pals fill the reunion with drinking, boys-will-be-boys antics and a few unexpected personal confessions. But, when the bonding devolves into accusations and regret, Paulie has to decide whether he's ready to tie the knot and take this big step into adulthood.

5.2

MagicScore

Four Weddings and a Funeral

1994

Over the course of five social occasions, a committed bachelor must consider the notion that he may have discovered love.

6.8

MagicScore

Corpse Bride

2005

In a 19th-century European village, a young man about to be married is whisked away to the underworld and wed to a mysterious corpse bride, while his real bride waits bereft in the land of the living.

7.6

MagicScore

Persuasion

1995

Living with her snobby family on the brink of bankruptcy, Anne Elliot is an unconforming woman with modern sensibilities. When Frederick Wentworth – the dashing one she once sent away – crashes back into her life, Anne must choose between putting the past behind her or listening to her heart when it comes to second chances.

7.1

MagicScore

Old Acquaintance

1943

Two writers, friends since childhood, fight over their books and lives.

7.0

MagicScore

Chaos Theory

2008

Frank Allen, a professional speaker who lectures on time management has a perfectly ordered and scheduled life, down to the minute. When his wife sets his clock forward 10 minutes as a joke, his day is thrown off. Deciding that his strictly ordered life has done him little good, he begins to make multiple choice index cards, choosing one at random and doing what is written on the card.

6.3

MagicScore

The Wood

1999

In the panicky, uncertain hours before his wedding, a groom with prenuptial jitters and his two best friends reminisce about growing up together in the middle-class African-American neighborhood of Inglewood, California. Flashing back to the twenty-something trio's childhood exploits, the memories capture the mood and nostalgia of the '80s era.

6.6

MagicScore

#10

The Wedding Singer

1998

Robbie, a local rock star turned wedding singer, is dumped on the day of his wedding. Meanwhile, waitress Julia finally sets a wedding date with her fiancée Glenn. When Julia and Robbie meet and hit it off, they find that things are more complicated than anybody thought.

6.8

MagicScore

#11

Ranma 1/2 the Movie: Big Trouble in Nekonron, China

1991

When Prince Kirin of the 7 Lucky Gods shows up at the Tendo dojo looking for his bride-to-be, guess who's accidentally holding the scroll that signifies his future mate? Why, Akane, of course, and the rest of the Ranma crew is forced to take a boat to China in order to save her from the horrors of marriage and a diet of pickled vegetables.

7.2

MagicScore

#12

Flying Down to Rio

1933

An American bandleader woos a Brazilian beauty who is already engaged to his employer. His friends try to help him, while learning the local dance, The Carioca. The first pairing of Fred Astaire & Ginger Rogers, and their only pre-Code film.

6.2

MagicScore

#13

Saving Silverman

2001

A pair of buddies conspire to save their best friend from marrying the wrong woman, a cold-hearted beauty who snatches him from them and breaks up their Neil Diamond cover band.

5.6

MagicScore

#14

The Sweetest Thing

2002

Christina's love life is stuck in neutral. After years of avoiding the hazards of a meaningful relationship, one night while club-hopping with her girlfriends, she meets Peter, her perfect match. Fed up with playing games, she finally gets the courage to let her guard down and follow her heart, only to discover that Peter has suddenly left town. Accompanied by Courtney, she sets out to capture the one that got away.

5.6

MagicScore

#15

In Her Shoes

2005

Irresponsible party girl Maggie is kicked out of her father's and stepmother's home—where she lives for free—and is taken in by her hard-working sister, Philadelphia lawyer Rose. After Maggie's disruptive ways ruin her sister's love life, Rose turns her out as well. But when their grandmother, who they never knew existed, comes into their lives, the sisters face some complicated truths about themselves and their family.

6.2

MagicScore

#16

Son of the Bride

2001

At age 42, Rafael Belvedere is having a crisis. He lives in the shadow of his father, he feels guilty about rarely visiting his aging mother, his ex-wife says he doesn't spend enough time with their daughter and he has yet to make a commitment to his girlfriend. At his lowest point, a minor heart attack reunites him with Juan Carlos, a childhood friend, who helps Rafael to reconstruct his past.

7.5

MagicScore

#17

Evening

2007

As Constance (Natasha Richardson) and Nina (Toni Collette) gather at the deathbed of their mother, Ann (Vanessa Redgrave), they learn for the first time that their mother lived an entire other lifetime during one evening 50 years ago. In vivid flashbacks, the young Ann (Claire Daines) spends one night with a man named Harris (Patrick Wilson), who was the love of her life.

5.8

MagicScore

#18

Kiss the Bride

2007

In high school, Matt and Ryan were best friends. More than friends, actually. But in the ensuing ten years, they've lost contact. So when Matt receives an invitation to Ryan's wedding he's surprised - especially that Ryan is marrying a woman!

4.7

MagicScore

#19

The Apartment

1996

Max is a former playboy who has decided to settle down by marrying his current love, Muriel. However, when Max catches a glimpse of the great lost love of his life, he becomes obsessed with rekindling their relationship.

6.7

MagicScore

#20

Lovers: A True Story

1991

Set in '50s Spain, a young man leaves the army and looks for a job so he and his fiancée can get married. He rents a room from a widow, and shortly begins a torrid affair with her. The fiancée figures it out and decides to win him back by offering herself to him and taking him to meet her family. Ultimately he has to make a decision. Based on a true story.

6.4

MagicScore

Frequently asked

What are the best movies like Kissing a Fool?

The top films similar to Kissing a Fool by MovieMagicScore are The Manxman (6.1), Sleep with Me (5.7), The Groomsmen (5.2). Each shares comedy/romance themes and is ranked by real viewer ratings, not critics or studios.

Is Kissing a Fool worth watching?

Kissing a Fool holds a MovieMagicScore of 5.5/10 from 71 viewer ratings.

What kind of movie is Kissing a Fool?

Kissing a Fool (1998) is a comedy, romance film directed by Doug Ellin, starring David Schwimmer, Jason Lee, Mili Avital.

Where can I find more recommendations like Kissing a Fool?

Browse the full ranked list above, or explore more comedy recommendations on MovieMagicScore, where every list is ordered by genuine viewer ratings.

Keep exploring

Movies like The Manxman Movies like Sleep with Me Movies like The Groomsmen Movies like Four Weddings and a Funeral Movies like Corpse Bride Movies like Persuasion

About movies like Kissing a Fool

This ranked list pairs Kissing a Fool (1998), a comedy and romance film from Doug Ellin, with similar titles by genre, theme and cast overlap (fans of David Schwimmer take note). Unlike critic-driven sites, every position here is ordered by MovieMagicScore — a rating built only from real viewers, with no studio marketing or paid placement. Scores update as more people rate, so the list stays current.

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