My Last Five Girlfriends

My Last Five Girlfriends

2010•1h 27m•5.3/10

DramaRomanceComedy

Ratings

🎬TMDb

5.3/10(43)

Depressed and suicidal, thirtysomething bachelor Duncan – determined to find the secret to a healthy, strong relationship, – flashes back to his last five relationships (in the last four years) and considers what caused each one to fail. Based on the novel 'Essays in Love' by Alain de Botton.

Open in PickFlick

Production

Tribeca Film Institute, Willing + Pilowsky Productions, Wire Films

Language

EN

Status

Released

Release Date

Trailers & Videos

Cast

Brendan Patricks

Brendan Patricks

Duncan

Kelly Adams

Kelly Adams

No. 1: Wendy

Jane March

Jane March

No. 2: Olive

Cécile Cassel

Cécile Cassel

No. 3: Rhona

Edith Bukovics

Edith Bukovics

No. 4: Natalie

Naomie Harris

Naomie Harris

No. 5: Gemma

Daniel Hoffmann-Gill

Daniel Hoffmann-Gill

Will

Sara Poyzer

No. 1 - Stewardess

Katie Stratford

No. 1 - Plane Passenger

Grant Sheehan

No. 1 - Plane Passenger

Johnny Ball

Johnny Ball

No. 1 - Self

Sally Christopher

No. 1 - Wendy's Boss

Ellen Hughes

No. 1 - Duncan's Sister

Duncan Wisbey

Duncan Wisbey

No. 1 - Divine Dating (voice)

Molly Line

No. 1 - Divine Dating Angel

John Line

No. 1 - God

Abigail Freeman

No. 1 - Young Wendy

Joe Malone

No. 1 - Young Duncan

Carole Philip

No. 1 - Duncan's Mother

Ian Smith

No. 1 - Duncan's Father

Recommended

The Heartbreak Kid

The Heartbreak Kid

Eddie, the 40-year-old confirmed bachelor finally says "I do" to the beautiful and sexy Lila. But during their honeymoon in Mexico, the woman of his dreams turns out to be a total nightmare, and the guy who could never pull the trigger realizes he’s jumped the gun.

The Heartbreak Kid

2007

5.7

Inside Out

Inside Out

When 11-year-old Riley moves to a new city, her Emotions team up to help her through the transition. Joy, Fear, Anger, Disgust and Sadness work together, but when Joy and Sadness get lost, they must journey through unfamiliar places to get back home.

Inside Out

2015

7.9

Shutter Island

Shutter Island

World War II soldier-turned-U.S. Marshal Teddy Daniels investigates the disappearance of a patient from a hospital for the criminally insane, but his efforts are compromised by troubling visions and a mysterious doctor.

Shutter Island

2010

8.2

Back to the Future

Back to the Future

Eighties teenager Marty McFly is accidentally sent back in time to 1955, inadvertently disrupting his parents' first meeting and attracting his mother's romantic interest. Marty must repair the damage to history by rekindling his parents' romance and - with the help of his eccentric inventor friend Doc Brown - return to 1985.

Back to the Future

1985

8.3

Ex Machina

Ex Machina

Caleb, a coder at the world's largest internet company, wins a competition to spend a week at a private mountain retreat belonging to Nathan, the reclusive CEO of the company. But when Caleb arrives at the remote location he finds that he will have to participate in a strange and fascinating experiment in which he must interact with the world's first true artificial intelligence, housed in the body of a beautiful robot girl.

Ex Machina

2015

7.6

Deadpool

Deadpool

The origin story of former Special Forces operative turned mercenary Wade Wilson, who, after being subjected to a rogue experiment that leaves him with accelerated healing powers, adopts the alter ego Deadpool. Armed with his new abilities and a dark, twisted sense of humor, Deadpool hunts down the man who nearly destroyed his life.

Deadpool

2016

7.6

Fantastic Beasts: The Crimes of Grindelwald

Fantastic Beasts: The Crimes of Grindelwald

Gellert Grindelwald has escaped imprisonment and has begun gathering followers to his cause—elevating wizards above all non-magical beings. The only one capable of putting a stop to him is the wizard he once called his closest friend, Albus Dumbledore. However, Dumbledore will need to seek help from the wizard who had thwarted Grindelwald once before, his former student Newt Scamander, who agrees to help, unaware of the dangers that lie ahead. Lines are drawn as love and loyalty are tested, even among the truest friends and family, in an increasingly divided wizarding world.

Fantastic Beasts: The Crimes of Grindelwald

2018

6.8

Joker

Joker

During the 1980s, a failed stand-up comedian is driven insane and turns to a life of crime and chaos in Gotham City while becoming an infamous psychopathic crime figure.

Joker

2019

8.1

Avatar

In the 22nd century, a paraplegic Marine is dispatched to the moon Pandora on a unique mission, but becomes torn between following orders and protecting an alien civilization.

Avatar

2009

7.6

The Avengers

The Avengers

When an unexpected enemy emerges and threatens global safety and security, Nick Fury, director of the international peacekeeping agency known as S.H.I.E.L.D., finds himself in need of a team to pull the world back from the brink of disaster. Spanning the globe, a daring recruitment effort begins!

The Avengers

2012

8.0

Once Upon a Time... in Hollywood

Once Upon a Time... in Hollywood

Los Angeles, 1969. TV star Rick Dalton, a struggling actor specializing in westerns, and stuntman Cliff Booth, his best friend, try to survive in a constantly changing movie industry. Dalton is the neighbor of the young and promising actress and model Sharon Tate, who has just married the prestigious Polish director Roman Polanski…

Once Upon a Time... in Hollywood

2019

7.4

Friends with Benefits

Friends with Benefits

Dylan is done with relationships. Jamie decides to stop buying into the Hollywood clichés of true love. When the two become friends they decide to try something new and take advantage of their mutual attraction - but without any emotional attachment.

Friends with Benefits

2011

6.6

Similar Movies

A Complete Unknown

A Complete Unknown

New York, early 1960s. Against the backdrop of a vibrant music scene and tumultuous cultural upheaval, an enigmatic 19-year-old from Minnesota arrives in the West Village with his guitar and revolutionary talent, destined to change the course of American music.

A Complete Unknown

2024

7.1

Do Something

Do Something

BC12, a red blood cell, lives and works in a body that is currently struggling with dehydration. He is given the task of traveling to Brian, the brain, and convincing him to drink some water. BC12 sets off on the journey and encounters various organs along the way, all of which have an opinion (sometimes more, sometimes less helpful) about Brian and his passivity.

Do Something

2025

Definitely, Maybe

Definitely, Maybe

When Will decides to tell his daughter the story of how he met her mother, he discovers that a second look at the past might also give him a second chance at the future.

Definitely, Maybe

2008

6.9

The Conformist

The Conformist

A weak-willed Italian man becomes a fascist flunky who goes abroad to arrange the assassination of his old teacher, now a political dissident.

The Conformist

1971

7.7

Süss, the Jew

Süss, the Jew

Nazi historical drama about Duke Karl Alexander of Württemberg and his treasurer Süß Oppenheimer.

Süss, the Jew

1940

4.3

The Watchmaker of St. Paul

The Watchmaker of St. Paul

Lyons, France. Michel Descombes is a watchmaker who lives alone with his teenage son Bernard. When the police visit and informs him that Bernard killed a man and is on the run with a girl, Michel realizes that he knew far less about his son than he thought.

The Watchmaker of St. Paul

1974

6.9

Summer Things

Summer Things

Two couple of friends, one very rich, the other almost homeless, decide to go on Holiday. Julie, a single mother, joins them too. Once at seaside, it starts a complicate love cross among them that will involve also a transsexual, a jealous brother, a Latin Lover and another nervous stressed couple. Not to mention about the daughter of one of them that is secretly in Chicago with one of her father's employees... At the end of the summer, all of them will join the same party...

Summer Things

2002

5.8

A Cock and Bull Story

A Cock and Bull Story

Steve Coogan, an arrogant actor with low self-esteem and a complicated love life, is playing the eponymous role in an adaptation of "The Life and Opinions of Tristram Shandy, Gentleman" being filmed at a stately home. He constantly spars with actor Rob Brydon, who is playing Uncle Toby and believes his role to be of equal importance to Coogan's.

A Cock and Bull Story

2005

6.1

An Accident

An Accident

In the 1980s, the building themes were transformed into bipolar moral dilemmas involving overly ambitious individuals who wanted to excel at any cost. The hero is the head of a demolition crew that demolishes large buildings, initially a sympathetic young man who, in the pursuit of career and accolades, begins to transgress the boundaries of what was then called socialist morality and legality. He gradually finds himself at odds with the principles of ordinary but honest people. The narrative's bland, proclamatory film is closely connected to its time of creation, and there are hardly any more timeless insights to be found.

An Accident

1986

90 Days

90 Days

A riveting story of love, integrity and compassion, 90 DAYS explores a beautiful couple's relationship and their life altering decision after ninety days of dating. Fueled with gripping performances by an extraordinary cast of actors led by Teyonah Parris and Nic Few, 90 DAYS is a groundbreaking cinematic piece of art that confronts the human experience of overcoming one of life's greatest perceived challenges. Written by Nathan Hale Williams and directed by Williams and Jennia Fredrique Aponte, the film is entertaining, authentic and a visual masterpiece. 90 Days is a film that will touch hearts while navigating the definition of ultimate compassion.

90 Days

2016

Holes

Holes

After being wrongfully convicted for stealing a pair of shoes, Stanley Yelnats is sent away to Camp Green Lake, a boys detention facility where inmates are forced to dig holes all day in the hot desert sun as a form of character building. But Stanley and the other boys start to unravel a mystery, linked with the camps tough-as-nails warden —and possibly Stanley’s family itself.

Holes

2003

6.9

Blindness

Blindness

When a sudden plague of blindness devastates a city, a small group of the afflicted band together to triumphantly overcome the horrific conditions of their imposed quarantine.

Blindness

2008

6.5