20 best movies like What About Brian (2006)

Can two serial cheaters get a second chance at love? After a one-night stand in college, New Yorkers Lainey and Jake meet by chance twelve years later and discover they each have the same problem: because of their monogamy-challenged ways, neither can maintain a relationship. Determined to stay friends despite their mutual attraction, they make a pact to keep it platonic, a deal that proves easier said than done.

By day, Nola Devlin (Poppy Montgomery) is an unassuming, frumpy magazine editor who is overlooked and teased by her coworkers. When the sun sets, though, and she is behind the glow and anonymity of her computer screen, she becomes the famous and “reclusive” advice columnist Belinda Apple. Nola’s friends, tired of being overworked and overweight, band together to create the “Cinderella Pact,” vowing to lose pounds by following the advice of their “fairy godmother,” Apple. When her secret identity is threatened, Nola is forced to take her own alter ego’s advice. But, as the group of friends drops dress sizes, their real issues are exposed, and better-than-expected life changes begin to blossom.

A modern retelling of Shakespeare's classic comedy about two pairs of lovers with different takes on romance and a way with words.

The story of two people caught in the routines of work and circles of friends. The days begin with an alarm and end with the fading sound of a television. Ron Hogan, a 28-year-old ATM parts purchaser, and Stacy Ryan, a 27-year-old, oddly charming courier, meet through a matchmaking Internet service and go through the routine of falling for one another.

Passions re-ignite and secrets revealed when a graphic designer reconnects with the great, lost love of his life for a weekend tryst at a house in the desert near Joshua Tree.

A determined teenage boy struggles to find acceptance within the Jr. Lifeguards of Hermosa Beach while juggling relationships and challenges in the summer of 1986.

When ambitious New York attorney Sam is sent to Shanghai on assignment, he immediately stumbles into a legal mess that could end his career. With the help of a beautiful relocation specialist, a well-connected old-timer, a clever journalist, and a street-smart legal assistant, Sam might just save his job, find romance, and learn to appreciate the beauty and wonders of Shanghai. Written by Anonymous (IMDB.com).

After false reports of his demise put him and his work on the map, an artist decides to continue the charade by posing as his own brother. Soon, a reporter enters his life and has a profound effect on him.

Jesse Sorensen ruled Florida as a pro skateboarder for over a decade. He had it all - a lucrative skateboarding contract, girls, fame and an extravagant lifestyle. Now six years later, past his prime and his usefulness in this youth-driven culture, Jesse is dropped by his skate team. Broke, he moves in with his elderly grandmother only to discover his 17-year old niece, Samantha, crashing there as well. She is following the same slippery slope Jesse once paved, with the hottest new skater in town. Jesse must confront what he has spent his entire life avoiding - responsibility - and figure out his future once and for all.

A self-help seminar inspires a sixty-something woman to romantically pursue her younger co-worker.

Mary and Ben are the star-crossed black sheep of two powerful families engaged in a centuries-long feud. When the pair reignite a romance after many years apart, their forbidden love draws a motley assortment of schemers and killers into their orbit, and as fists and bullets fly, it becomes clear that violent delights will have violent ends.

Four lovers find themselves caught in a tangle of intersecting relationships in this engaging, New York-set romantic drama that explores the ripple effects of love and obsession.

In the year after graduating college, Izzy struggles to navigate the seemingly incessant failures of adulthood, the reality of a substandard dating pool and a debilitating fear of top-sheets, all in between X-Files marathons. Comically unsuccessful in love over the course the year, including five half-hearted relationships with astoundingly self-centered men, Izzy resigns herself to the support of her mother and sister, who are struggling with their own relationship problems. Seeing herself in them, Izzy gradually gains the confidence to be honest and vulnerable.

A coming of age story about a washed up twenty something year old, the onetime hometown hero and track star, who is convinced by a local sweetheart to run a marathon and get his life back on track.

While traveling abroad, a guy falls for a Romanian beauty whose unreachable heart has its origins in her violent, charismatic ex.

BOY MEETS GIRL is a funny, tender, sex positive romantic comedy that explores what it means to be a real man or woman, and how important it is to live a courageous life not letting fear stand in the way of going after your dreams.

The continuing adventures of the Portokalos family. A follow-up to the 2002 comedy, "My Big Fat Greek Wedding."

A group of high school Seniors juggle between old loves and new flings on the shores of a beautiful Italian town.

When event planner Chloe is hired to plan the local Christmas Festival, she is beyond thrilled to embrace the challenge. Professionally, everything is going great, but much to the dismay of her mother, Chloe confesses she has given up on ever finding Mr. Right. That all changes the night of the opening of the festival when she meets Evan. The two begin a whirlwind romance, but as Christmas Day nears, Chloe learns that Evan is being transferred overseas for work. What follows is three more Christmases where Chloe and Evan cross paths at the annual festival, but each year something - or someone - stands in the way of true love. Will a touch of Santa's magic on their fourth Christmas Eve finally bring them together?

A case of mistaken identity results in unexpected romance when the most popular girl in high school and the biggest loser must come together to win over their crushes.

Though a childhood bout with polio left him dependent on an iron lung, Mark O'Brien (John Hawkes) maintains a career as a journalist and poet. A writing assignment dealing with sex and the disabled piques Mark's curiosity, and he decides to investigate the possibility of experiencing sex himself. When his overtures toward a caregiver scare her away, he books an appointment with sex surrogate Cheryl Green (Helen Hunt) to lose his virginity.

Jamie is a New York-based executive recruiter who entices Dylan, an art director from Los Angeles, to take a job at the New York office of GQ magazine. Finding that they have much in common, the two become fast friends. Feeling jaded by a number of broken romances, Dylan and Jamie decide that they are ready to quit looking for true love and focus on having fun. However, complications unfold when the two best pals add sex to their relationship.

When college friends reunite after 15 years over the Christmas holidays, they discover just how easy it is for long-forgotten rivalries and romances to be reignited.

A coming-of-age story that follows 12-year-old Andy Nichol, a bright student who, like most kids his age, will do anything to avoid conflict for fear of suffering overwhelming ridicule and punishment from his junior high school peers.

The Four Faced Liar is a story of love and lies for four twenty-somethings looking to find themselves in New York City... A story of love and lies for four twenty-somethings looking to find themselves in New York City. A pair of best friends and a seemingly perfect couple meet at a local Irish pub tucked in the winding streets of the West Village. Through their chance meeting, the four bond and over time all of their relationships with one another morph into love, betrayal and heartbreak for all.

A clinically depressed teenager gets a new start after he checks himself into an adult psychiatric ward.

Former prom king and college freshman Scott returns home for Thanksgiving break and gets dumped by his long-term girlfriend. With his world turned upside down, Scott strikes an unlikely friendship with former classmate Tori, an ugly duckling who blossomed in her first semester of college, and they embark on an outrageous adventure through their hometown. But when Scott and Tori start falling in love, they realize that a few months away may have changed them more than they realized.

A charming romance develops between a boy with one eye and an overweight girl, though when she loses weight after going to college, their relationship is tested in devastating ways they never dreamed would happen.

Mathias Gold is a down-on-his-luck New Yorker who inherits a Parisian apartment from his estranged father. But when he arrives in France to sell the vast domicile, he's shocked to discover a live-in tenant who is not prepared to budge. His apartment is a viager—an ancient French real estate system with complex rules pertaining to its resale—and the feisty Englishwoman Mathilde Girard, who has lived in the apartment with her daughter Chloé for many years, can by contract collect monthly payments from Mathias until her death.

When journalist Julia goes back home to find inspiration, she discovers her childhood friend has built a giant snow maze which prompts her to find her way to true love.

A romantic comedy that brings together three disparate characters who are learning to face a challenging and often confusing world as they struggle together against a common demon: sex addiction.