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Home›Movies›Comedy›2000s Comedy Movies for Date Night on Plex

Tag Mix

2000s Comedy Movies for Date Night on Plex

32movies

Comedy ×
Date Night ×
2000s ×
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32movies

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+ Romantic1039 + Dialogue-Heavy883 + Emotional782 + Funny764 + Feel-Good589 + Book537 + Slow Burn436 + Dark383 + Parents372 + Friends328 + Under 2 Hours

Stranger Than Fiction (2006) poster

Stranger Than Fiction

2006Comedy · Drama1h 53m

Thought-Provoking Whimsical Heartwarming Smart Twist Ending

Just My Luck (2006) poster

Just My Luck

2006Comedy · Fantasy1h 43m

Romantic Funny Feel-Good New York Teens

Secretary (2002) poster

Secretary

2002Comedy · Drama1h 51m

Weird Dark Romantic Quotable Date Night

No Reservations (2007) poster

No Reservations

2007Comedy · Drama1h 44m

Feel-Good Heartwarming Romantic Date Night Parents

Penelope (2007) poster

Penelope

2007Comedy · Fantasy1h 44m

Feel-Good Whimsical Heartwarming Date Night Family

Rumor Has It... (2005) poster

Rumor Has It...

2005Comedy · Romance1h 37m

Feel-Good Funny Dysfunctional Family Dialogue-Heavy Date Night

The Nanny Diaries (2007) poster

The Nanny Diaries

2007Comedy · Drama1h 45m

Feel-Good Funny Dysfunctional Family Fish Out of Water New York

Uptown Girls (2003) poster

Uptown Girls

2003Comedy · Drama1h 32m

Heartwarming Feel-Good Funny Friendship New York

Bandits (2001) poster

Bandits

2001Comedy · Crime2h 3m

Funny Dark Feel-Good Heist Prison Break

Heartbreakers (2001) poster

Heartbreakers

2001Comedy · Crime2h 3m

Funny Strong Female Lead Con Artist Stylish Friends

The Rebound (2009) poster

The Rebound

2009Comedy · Romance1h 35m

Romantic Funny Feel-Good New York Date Night

Spread (2009) poster

Spread

2009Comedy · Romance1h 38m

Dark Los Angeles Stylish Date Night

After the Sunset (2004) poster

After the Sunset

2004Action · Comedy1h 37m

Feel-Good Funny Heist Cops Island

But I'm a Cheerleader (2000) poster

But I'm a Cheerleader

2000Comedy · Drama1h 25m

Funny Thought-Provoking Whimsical Coming-of-Age Campy

The Curse of the Jade Scorpion (2001) poster

The Curse of the Jade Scorpion

2001Comedy · Crime1h 43m

Funny Whimsical New York Dialogue-Heavy Retro

My Best Friend's Girl (2008) poster

My Best Friend's Girl

2008Comedy · Romance1h 41m

Funny Love Triangle Wedding Friendship Dialogue-Heavy

The Brothers Bloom (2008) poster

The Brothers Bloom

2008Adventure · Comedy1h 54m

Whimsical Bleak Romantic Con Artist Europe

Anything Else (2003) poster

Anything Else

2003Comedy · Drama1h 48m

Emotional Funny New York Dialogue-Heavy Date Night

Life or Something Like It (2002) poster

Life or Something Like It

2002Comedy · Drama1h 43m

Feel-Good Uplifting Date Night

New York, I Love You (2008) poster

New York, I Love You

2008Comedy · Drama1h 43m

Romantic Funny Heartwarming New York Anthology

The Accidental Husband (2008) poster

The Accidental Husband

2008Comedy · Romance1h 30m

Romantic Funny Feel-Good Love Triangle Revenge

New in Town (2009) poster

New in Town

2009Comedy · Romance1h 37m

Feel-Good Heartwarming Funny Fish Out of Water Winter

Return to Me (2000) poster

Return to Me

2000Comedy · Romance1h 56m

Feel-Good Heartwarming Romantic Dialogue-Heavy Date Night

Chaos Theory (2008) poster

Chaos Theory

2008Comedy · Drama1h 27m

Funny Feel-Good Wedding Nonlinear Date Night

I Could Never Be Your Woman (2007) poster

I Could Never Be Your Woman

2007Comedy · Drama1h 37m

Romantic Funny Feel-Good Dialogue-Heavy Date Night

2 Days in Paris (2007) poster

2 Days in Paris

2007Comedy · Romance1h 36m

Funny Romantic Fish Out of Water Paris Dialogue-Heavy

Wedding Daze (2006) poster

Wedding Daze

2006Comedy · Romance1h 30m

Funny Chaotic Wedding Friends Date Night

My Sassy Girl (2008) poster

My Sassy Girl

2008Comedy · Romance1h 36m

Funny Romantic New York Date Night Remake

Management (2009) poster

Management

2009Comedy · Drama1h 34m

Feel-Good Romantic Dialogue-Heavy Date Night

200 Pounds Beauty (2006) poster

200 Pounds Beauty

2006Comedy · Drama1h 56m

Language: Korean

Feel-Good Funny Heartwarming Friends Date Night

Jab We Met (2007) poster

Jab We Met

2007Comedy · Drama2h 18m

Language: Hindi

Romantic Feel-Good Funny Road Trip Strong Female Lead

10 Items or Less (2006) poster

10 Items or Less

2006Comedy · Drama1h 21m

Feel-Good Heartwarming Los Angeles Slow Burn Dialogue-Heavy