Most Similar Movies to Gregory's Two Girls (1999)


If you are looking for movies like Gregory's Two Girls (1999), you might like movies tagged with keyword : teacher, student, young girl, businessman, love interest, friend, amusing, engaging, witty, playful, lighthearted, heartwarming, school, relationships, sexual fantasy, heist, adventure, growing up, forbidden love, love, pursuit, temptation, 1990s .


Chasing the Blues (2017), Hello Down There (1969), 21 Jump Street (2012), Lucas (1986), The Rewrite (2014), The English Teacher (2013), Big Bully (1996) ... Let's take a look at the following list...

Chasing the Blues (2017)

Chasing the Blues (2017)

7.0/10 Comedy

Two rival record collectors attempt to con an old lady out of a rare, but cursed, 1930s Blues record. When a series of unfortunate circumstances lands them in jail, the feud festers for over twenty years until they are released from prison and get a second chance at snagging the vinyl, this time from a more formidable foe.

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Hello Down There (1969)

Hello Down There (1969)

5.9/10 Comedy

A marine scientist volunteers to have his family live in a prototype underwater home to prove it's practical.

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21 Jump Street (2012)

21 Jump Street (2012)

7.2/10 Action, Comedy, Crime

A pair of underachieving cops are sent back to a local high school to blend in and bring down a synthetic drug ring.

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Lucas (1986)

Lucas (1986)

6.9/10 Comedy, Drama, Romance

A socially inept fourteen-year-old experiences heartbreak for the first time when his two best friends - Cappie, an older-brother figure, and Maggie, the new girl with whom he is in love - fall for each other.

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The Rewrite (2014)

The Rewrite (2014)

6.2/10 Comedy, Romance

An Oscar-winning writer in a slump leaves Hollywood to teach screenwriting at a college on the East Coast, where he falls for a single mom taking classes there.

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The English Teacher (2013)

The English Teacher (2013)

5.8/10 Comedy, Drama

An English teacher's life is disrupted when a former student returns to her small town after failing as a playwright in New York.

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Big Bully (1996)

Big Bully (1996)

4.7/10 Comedy

A writer returns to his hometown where he faces the childhood nemesis whose life he ultimately ruined, only the bully wants to relive their painful past by torturing him once again.

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Summer School (1987)

Summer School (1987)

6.6/10 Comedy, Romance

Freddy the gym teacher has to teach remedial English in summer (high) school, if he wants tenure. As he can only teach gym and his students want fun, emphasis is on "field trips" - until he's fired unless all his students pass the test.

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Summer School (1987)

Summer School (1987)

6.3/10 Comedy

The vice principal (Robin Thomas) makes a high-school gym teacher (Mark Harmon) teach catch-up English to a group of misfits.

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Please Sir! (1971)

Please Sir! (1971)

6.2/10 Comedy

Mr Hedges takes his class on a field trip, with disastrous consequences.

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Day of the Flowers (2012)

Day of the Flowers (2012)

5.5/10 Romance, Comedy, Drama, Horror

Two Scottish sisters, one a left-wing activist, the other a popular party girl, travel to Cuba to scatter their late father's ashes. In losing and trying to reclaim their father's ashes, the bickering sisters set off on a journey that them takes them through romance, danger, and the discovery of old family secrets.

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Fame (2009)

Fame (2009)

5.0/10 Comedy, Drama, Musical, Romance

An updated version of the musical Fame (1980), which centered on the students of the New York Academy of Performing Arts.

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Rory O'Shea Was Here (2004)

Rory O'Shea Was Here (2004)

7.8/10 Comedy, Drama

When the kinetic Rory moves into his room in the Carrigmore Residential Home for the Disabled, his effect on the home is immediate. Most telling is his friendship with Michael, a young man with cerebral palsy and nearly unintelligible speech. Somehow, Rory understands Michael, and encourages him to experience life outside the confines of home.

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Of Horses and Men (2013)

Of Horses and Men (2013)

10.0/10 Comedy, Drama

Vignettes of life in a rural Icelandic community show the intertwined lives of humans (Helgi Björnsson, Maria Ellingsen, Kristbjörg Kjeld) and equines.

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The F Word (2013)

The F Word (2013)

6.8/10 Comedy, Romance

Wallace, who is burned out from a string of failed relationships, forms an instant bond with Chantry, who lives with her longtime boyfriend. Together, they puzzle out what it means if your best friend is also the love of your life.

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Pretty in Pink (1986)

Pretty in Pink (1986)

6.8/10 Comedy, Drama, Romance

A poor girl must choose between the affections of dating her childhood sweetheart or a rich but sensitive playboy.

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Spud (2010)

Spud (2010)

6.7/10 Comedy

It's South Africa 1990. Two major events are about to happen: The release of Nelson Mandela and, more importantly, it's Spud Milton's first year at an elite boys only private boarding school.

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Flirting (1990)

Flirting (1990)

9.6/10 Comedy, Drama

A white preppie (Noah Taylor) loves a Ugandan girl (Thandie Newton) in 1965 Australia in this sequel to "The Year My Voice Broke."

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