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90s / early 00s rom-coms ranked

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50 films · Updated September 17, 2025

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50 films

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Genre

Year

Bridget Jones's Diary

2001

7.1Flick0.0You

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13 Going on 30

2004

7.4Flick0.0You

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While You Were Sleeping

1995

7.5Flick0.0You

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When Harry Met Sally...

1989

8.2Flick0.0You

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Confessions of a Shopaholic

2009

6.9Flick0.0You

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Just Like Heaven

2005

6.8Flick0.0You

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Legally Blonde

2001

7.8Flick0.0You

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10 Things I Hate About You

1999

8.2Flick0.0You

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Dirty Dancing

1987

7.5Flick0.0You

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27 Dresses

2008

7.3Flick0.0You

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First Daughter

2004

6.0Flick0.0You

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The Lake House

2006

6.9Flick0.0You

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You've Got Mail

1998

7.2Flick0.0You

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Clueless

1995

7.3Flick0.0You

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The Princess Diaries 2: Royal Engagement

2004

7.2Flick0.0You

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The Holiday

2006

7.3Flick0.0You

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He's Just Not That Into You

2009

6.5Flick0.0You

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Say Anything...

1989

7.2Flick0.0You

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Serendipity

2001

6.8Flick0.0You

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Jerry Maguire

1996

7.3Flick0.0You

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How to Lose a Guy in 10 Days

2003

7.7Flick0.0You

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(500) Days of Summer

2009

7.4Flick0.0You

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Bridget Jones: The Edge of Reason

2004

6.5Flick0.0You

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Letters to Juliet

2010

7.2Flick0.0You

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Enchanted

2007

7.3Flick0.0You

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She's All That

1999

6.1Flick0.0You

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The Cutting Edge

1992

7.1Flick0.0You

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Shakespeare in Love

1998

6.4Flick0.0You

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Bride Wars

2009

6.4Flick0.0You

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Hitch

2005

6.4Flick0.0You

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Runaway Bride

1999

6.4Flick0.0You

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Pretty Woman

1990

7.4Flick0.0You

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Just My Luck

2006

6.4Flick0.0You

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Love Actually

2003

7.1Flick0.0You

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Ella Enchanted

2004

7.2Flick0.0You

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Maid in Manhattan

2002

6.2Flick0.0You

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The Prince & Me

2004

6.1Flick0.0You

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The Cutting Edge: Chasing the Dream

2008

6.9Flick0.0You

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The Ugly Truth

2009

5.7Flick0.0You

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Valentine's Day

2010

6.1Flick0.0You

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She's the Man

2006

7.2Flick0.0You

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My Best Friend's Wedding

1997

6.4Flick0.0You

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Prime

2005

6.8Flick0.0You

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The Cutting Edge: Going for the Gold

2006

6.8Flick0.0You

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Captain Corelli's Mandolin

2001

6.8Flick0.0You

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Catch and Release

2006

6.3Flick0.0You

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Metroland

1997

7.0Flick0.0You

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Four Weddings and a Funeral

1994

6.6Flick0.0You

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The Good Guy

2009

6.9Flick0.0You

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Never Been Kissed

1999

5.3Flick0.0You

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