Best movies like My Date with Drew

A unique, carefully handpicked, selection of the best movies like My Date with Drew Starring Drew Barrymore, Brian Herzlinger, Corey Feldman, Eric Roberts, and more. If you liked My Date with Drew then you may also like: 20 Dates, Youth in Revolt, We'll Never Have Paris, Wicker Park, Joe Versus the Volcano and many more popular movies featured on this list. You can further filter the list even more or get a random selection from the list of similar movies, to make your selection even easier.

Ever since the second grade when he first saw her in E.T. The Extraterrestrial, Brian Herzlinger has had a crush on Drew Barrymore. Now, 20 years later he's decided to try to fulfill his lifelong dream by asking her for a date. There's one small problem: She's Drew Barrymore and he's, well, Brian Herzlinger, a broke 27-year-old aspiring filmmaker from New Jersey.

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20 Dates

Myles is divorced in L.A. He wants a love life and a film career. So he decides to go on 20 dates and find true love in front of a camera, making his first feature. His patient agent, Richard, finds a $60,000 investor, the shadowy Elie. Myles starts his search, sometimes telling his date she's being filmed, sometimes not. Elie wants sex and titillation, Myles wants it "real." Myles regularly talks with his old film teacher, Robert McKee, who wonders if love is possible in modern life. Half-way through the 20 dates, Myles meets Elisabeth; she's everything he desires and she likes him. Can he finish the 20 dates, satisfy Elie, and complete his film without losing Elisabeth?

Youth in Revolt

As a fan of Albert Camus and Jean-Luc Godard, teenage Nick Twisp is definitely out of his element when his mother and her boyfriend move the family to a trailer park. When a pretty neighbor named Sheeni plays records by French crooners, it's love at first sight for frustrated and inexperienced Nick. Learning that she is dating someone, Nick launches a hilarious quest to find his way into Sheeni's heart -- and bed.

We'll Never Have Paris

Quinn, a neurotic man, is diagnosed with a harmless eye condition and soon after his life spirals out of control. He second-guesses his plans to propose to his longtime girlfriend, Devon, after his beautiful coworker, Kelsey, confesses that she has a crush on him. After a conversation with his best friend, Jameson, he clumsily tries to explain his doubts to Devon, but his possible proposal turns into a break-up. When Devon flees to Paris, he follows her in a last-ditch effort to win back "the one."

Wicker Park

Matthew, a young advertising executive in Chicago, puts his life and a business trip to China on hold when he thinks he sees Lisa, the love of his life who left him without a word two years earlier, walking out of a restaurant one day.

Joe Versus the Volcano

Hypochondriac Joe Banks finds out he has six months to live, quits his dead end job, musters the courage to ask his co-worker out on a date, and is then hired to jump into a volcano by a mysterious visitor.

Celeste & Jesse Forever

Celeste and Jesse met in high school and got married young. They laugh at the same jokes and finish each other’s sentences. They are forever linked in their friends’ minds as the perfect couple – she, a high-powered businesswoman and budding novelist; he, a free spirit who keeps things from getting boring. Their only problem is that they have decided to get divorced. Can their perfect relationship withstand this minor setback?

The Perfect Daughter

Finding his daughter confused and drunk one night, Martin overreacts and puts a wedge between their once idyllic relationship at a time when she'll need him the most.

Confessions of a Teenage Drama Queen

Lola is an ambitious teenager who aspires to be a famous stage actress, but ger dream of performing on Broadway suffers a setback when her family moves from New York City to suburban New Jersey. Determined to make the best of it, however, Lola embarks on a mission to become the most popular girl at her high school, a goal that sets her on a collision course with the catty Carla Santini.

The Girl Next Door

Exceptionally ambitious high schooler Matthew has aspirations for a career in politics when he falls in love with his gorgeous 19-year-old neighbor, Danielle. But Matthew's bright future is jeopardized when he finds Danielle was once a porn star. As Danielle's past catches up with her, Matthew's love for her forces him to re-evaluate his goals.

Julie & Jack

In this love story with Hitchcockian overtones, a computer chip salesman meets the perfect girl (a brilliant software developer) -- and then she disappears. After Jack Livingstone (Justin Kunkle) finds Julie Romanov (Jenn Gotzon) through an Internet dating service, he's convinced life is perfect. But when she vanishes, he's left distraught and confused. Turning to Julie's mother (Hitchcock vet Tippi Hedren), he learns a startling revelation.

Down to the Sea in Ships

During a whaling expedition in the late 1800's, the aging Captain Bering Joy (Lionel Barrymore) and his new first mate, Dan Lunceford (Richard Widmark) engage in a battle of wills concerning the education of the captain's struggling grandson.

Fever Pitch

A romantic comedy about a man, a woman and a football team. Based on Nick Hornby's best selling autobiographical novel, Fever Pitch. English teacher Paul Ashworth believes his long standing obsession with Arsenal serves him well. But then he meets Sarah. Their relationship develops in tandem with Arsenal's roller coaster fortunes in the football league, both leading to a nail biting climax.

Fever Pitch

Lindsay is stuck in the middle of her relationship with Ben and his passion for the Boston Red Sox.

The Fabelmans

Growing up in post-World War II era Arizona, young Sammy Fabelman aspires to become a filmmaker as he reaches adolescence, but soon discovers a shattering family secret and explores how the power of films can help him see the truth.

Hav Plenty

Lee Plenty is an almost broke would-be novelist and Havilland Savage is a rich and very beautiful woman and his friend. When she invites him to her home for New Year's Eve, they start to build up a romance.

Sherman's March

Ross McElwee sets out to make a documentary about the lingering effects of General Sherman's march of destruction through the South during the Civil War, but is continually sidetracked by women who come and go in his life, his recurring dreams of nuclear holocaust, and Burt Reynolds.

Princess Cut

A lifelong Carolina farm girl, now in her early 20's, Grace has dreamed all her life of the day when "Mr. Right" slips a Princess Cut diamond on her finger and swears to love her forever. Tonight may be that night as Stewart has something special planned after 15 months together! But when things don't go as planned, and romance crashes down around her, it launches her on a quest, aided by her father, to understand what it means to truly love another person. Will Grace finally discover love or ruin her chances for happiness forever?

Bright Leaves

Ross McElwee travels through the North Carolina tobacco belt in search of the ancient southern traditions associated with tobacco growing and use, while comparing his filmmaking to commercial cinema, represented by Bright Leaf, a melodrama directed by Michael Curtiz in 1950, starring Gary Cooper, apparently based on the life of his great-grandfather.

Twinkle All the Way

To pull off a spectacular Christmas-themed wedding, a wedding planner joins forces with the co-owner of a family-run Christmas decoration and house-lighting company.

Spielberg

A documentary on the life and career of one of the most influential film directors of all time, Steven Spielberg.

Tortured Dust

The culmination of a series of autobiographical films that Brakhage made about his family (collectively known as The Book of Family), Tortured Dust was shot as the filmmaker's children from his first marriage were beginning to leave the house, and edited during Brakhage and his first wife Jane's impending separation. The first half concentrates on Brakhage's teenage sons as they move around the cabin that has been their home for almost 20 years, and the second half turns towards the filmmaker's three daughters.

A Christmas Movie Christmas

Eve is a Christmas movie fanatic and dreams of having a movie-perfect Christmas with a movie-perfect boyfriend. On Christmas Eve, when Eve and her cynical sister Lacy make wishes to Santa, they wake up in Christmas Town and find themselves trapped inside a Christmas movie where they are the stars. But when things start to go wrong, and Eve's knowledge of all things Christmas movie fails to fix things, Eve and Lacy try to find a way out of the picture-perfect Christmas and back to reality.

Reindeer Games Homecoming

When her father dies, MacKenzie keeps his tradition of the town's fundraising "The Reindeer Games" alive, but when high school crush Chase shows up and plays against her, the spark between them is undeniable.

Love's Last Resort

After ten years of dating, Chloe’s boyfriend Eric still hasn’t matured. Hoping to give him the push he needs, she dumps him; confident Eric will grow up and beg her to come back. However, six months later, Eric meets Chloe for dinner with big news: he’s getting married in a week. Needing a break to mend her broken heart, Chloe takes a vacation, but when she arrives, she learns that Eric and his fiancée are getting married at the same resort!

The Holiday Dating Guide

Dating coach and aspiring book author Abigale Slater is tasked by her publisher Jack to prove that her dating advice really works. With that, she decides to make a man fall for her by Christmas Eve in 12 days. When she Michael Ryan, her single-minded mission takes an unexpected turn.

How Sweet It Is

An alcoholic theater owner needs to put together a successful musical in order to pay off his mob debt, but problems arise when the wise guys want to cast their friends in the production.

My Summer With Des

Romantic comedy set during the European football championships in 1996, where football fan Martin finds his life is going from bad to worse after losing his job and splitting up with his girlfriend. However, as the football tournament progresses his luck begins to turn, firstly because of England's successes on the pitch, and secondly because of his encounter with a mysterious woman.

It's All Good

Aaron, Vinny and Cooper are dead broke and ready to give up on their pursuit of becoming big shot filmmakers. Desperate to keep the dream alive, they turn to crowdfunding for their first feature film and raise $75,000 dollars. However, they are overtaken by greed and instead blow the money on frivolous luxuries. Now they must face the consequences, including some shady acquaintances interested in their fortune, and an onslaught of angry donors who have been deceived.

Courting Courtney

Filmmaker Nick has decided to make a documentary about his best friend Courtney's love life. Courtney, a schoolteacher, has had a two-year on and off relationship with a guy who can't commit; she's also tried video-dating and a women's group. She never thought she'd have a problem finding the right guy and falling in love, but as she gets closer and closer to 30 she gets more and more desperate. Nick, on the other hand, is having as much trouble finding the right girl, and when his true feelings for Courtney come to light, they have to decide whether or not to stay just friends.

The Walls Are Watching

A young couple is terrorized by the former owner of the home they now occupy. Instead of a honeymoon, life becomes a cat and mouse game for these newlyweds as they try to survive being hunted by a man who knows every inch of the residence better than they do; and who has nothing left to lose.

The Holiday Fix Up

When Sam, the designer behind a popular home renovation show, returns to her hometown during the holidays to help renovate the Bell Harbor Inn, she gets paired with Coop as her lead contractor. The only problem — he's the guy who broke her heart and she's the one who got away. Sparks fly as they work closely to get the renovations done in time for the inn's annual Christmas Eve Harborfest.

A Christmas Dance Reunion

Lucy Mortimer, a successful attorney who returns with her mum to their old Christmas getaway - the Winterleigh Resort - which is on the brink of closing down for good. Much to her surprise, Lucy is reunited with her childhood Christmas dance partner Barrett Brewster and the pair give the resort a new lease of life as the passion between them heats up.

Suddenly, Love

Young lovers — she's a child of the ghetto, determined to escape her alcoholic, bickering parents; he's a socially prominent attorney with a long-standing health problem — attempt to defy every obstacle to their romance and ultimate marriage.

Dreaming Lhasa

Karma, a Tibetan filmmaker from New York, goes to Dharamsala, the Dalai Lama's exile headquarters in northern India, to make a documentary about former political prisoners who have escaped from Tibet. She wants to reconnect with her roots but is also escaping a deteriorating relationship back home.One of Karma's interviewees is Dhondup, an enigmatic ex-monk who has just escaped from Tibet. He confides in her that his real reason for coming to India is to fulfill his dying mother's last wish, to deliver a charm box to a long-missing resistance fighter. Karma finds herself unwittingly falling in love with Dhondup even as she is sucked into the passion of his quest, which becomes a journey into Tibet's fractured past and a voyage of self-discovery

Return to Campus

A 55-year-old former high school football player finally gets to fulfill his life-long dream and play in the big game in this autobiographical fantasy.

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