20 best movies like Sydney White (2007)

Ryan and Jennifer are opposites who definitely do not attract. At least that's what they always believed. When they met as twelve-year-olds, they disliked one another. When they met again as teenagers, they loathed each other. But when they meet in college, the uptight Ryan and the free-spirited Jennifer find that their differences bind them together and a rare friendship develops.

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.

Thirty-nine-year old divorcé Louise Harrington (Linney) works in the admissions office at Columbia University School of the Arts. She is unnerved when she receives an application from F. Scott Feinstadt, the same name of her high school sweetheart who was killed in a car crash, and calls the student to arrange an interview. His appearance, mannerisms, and painting style closely resemble those of her former love, and she begins to suspect the young artist may be the reincarnation of her old flame. Hours after meeting, the two embark upon an affair. Also complicating Louise's life are her relationship with her ex-husband Peter , who confesses he is learning to cope with a sex addiction that, unknown to her, plagued their marriage; her ne'er-do-well brother Sammy, who is favored by their mother Ellie despite his shortcomings; and her best friend Missy, who stole the original Scott from Louise before his death and seems intent on doing the same with the contemporary version.

Nerdy high schooler Ronald Miller rescues cheerleader Cindy Mancini from parental punishment after she accidentally destroys her mother's designer clothes. Ronald agrees to pay for the $1,000 outfit on one condition: that she will act as though they're a couple for an entire month. As the days pass, however, Cindy grows fond of Ronald, making him popular. But when Ronald's former best friend gets left behind, he realizes that social success isn't everything.

A trio of beautiful girls set out to revolutionize life at a grungy American university: the dynamic leader Violet Wister, principled Rose and sexy Heather. They welcome transfer student Lily into their group which seeks to help severely depressed students with a program of good hygiene and musical dance numbers.

Four black students attend an Ivy League college where a riot breaks out over an “African-American” themed party thrown by white students. With tongue planted firmly in cheek, the film explores racial identity in 'post-racial' America while weaving a story about forging one's unique path in the world.

The President's daughter, unable to experience life like a normal 18 year-old, escapes from her entourage of Secret Service agents while traveling in Europe. She falls in love with a handsome British stranger, who also happens to be working undercover for her father.

A recent college graduate sets out to win back the girl of his dreams.

Eight close friends soak up their last day of summer together on the beach before parting ways for college.

Grand romantic gestures need not apply in this comedic tale of star-crossed young love. Instead, freshman Brian Kieslowski displays endless reserves of bumbling awkwardness as he goes home with a girl for the first time... and then learns that he got her pregnant... with twins... all while she's going through a rather inconvenient Christianity phase. Could it be that being the good guy and doing what's right are two very different things?

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.

Two students at neighboring colleges get swept up in first love. Pookie Adams, a kooky misfit with no family or friends, clings to the quiet and studious Jerry, who has the ability to make a choice of living in Pookie's private world or be accepted by the society that Pookie rejects. Unwittingly, it is through their awkward relationship that Pookie prepares Jerry for the world of "weirdos" that she doesn't fit into.

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.

When nerdy high schooler Dani finally attracts the interest of her longtime crush, she lands in the cross hairs of his ex, a social media celebrity.

Easy-going, gentle college-boy Adam Baker enjoys frat-life, however disgusting the frat-house gets because of his sloppy house-mates Freddie, Ferguson and Munch. Then Adam meets Eve, starts falling in love, but gets jealous of frat-brother Billy, who 'bumps' almost constantly without seeking love, while Eve guards her campus-unique virginity. As even his thrice-divorced dad, an MD, urges Adam to get laid rather then loved, his patience runs out against healthy hormones

Set in New York City in the sweltering summer, The Wackness tells the story of a troubled teenage drug dealer, who trades pot for therapy sessions with a drug-addled psychiatrist. Things get more complicated when he falls for one of his classmates, who just happens to be the doctors daughter. This is a coming-of-age story about sex, drugs, music and what it takes to be a man.

Dylan Schoenfield is the pink princess of the upscale Los Angeles Woodlands Academy. She has the coolest boyfriend, the most popular friends, and a brand-new it bag that everyone covets. But when she accidentally tosses her Serge Sanchez bag into a fountain, this princess comes face-to-face with her own personal frog, self-professed film geek Josh Rosen. In return for rescuing Dylan's bag, Josh convinces Dylan to let him film her for his documentary on high school popularity. Reluctantly, Dylan lets F-list Josh into her A-list world, and is shocked to realize that sometimes nerds can be pretty cool. But when Dylan's so-called prince charming of a boyfriend dumps her flat, her life and her social status comes to a crashing halt. Can Dylan win the Woodlands Academy Fall Formal Blossom Queen crown? Can Josh win the Woodlands Academy 10th Annual Film Festival? Can Dylan, with Josh's help, pull the pieces together to create her own happily-ever-after?

A pregnant New York social worker begins to develop romantic feelings for her gay best friend, and decides she'd rather raise her child with him, much to the dismay of her overbearing boyfriend.

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.

Young mattress salesman Brian decides to adopt a baby from China but is distracted when he forms a relationship with quirky, wealthy Harriet whom he meets at his mattress store. As their relationship flourishes, unbeknownst to them, a hitman is trying to kill Brian.

Natalie allows her classmate Jeff, who ran away from home after a fight with his stepfather, to stay at her place while her father is away on a business trip. Natalie soon starts dating Jeff's friend James Casey, who isn't as faithful as she thinks, while her best friend Polly falls in love with baseball player Zoo Knudsen.

Straitlaced Princeton University admissions officer, Portia Nathan is caught off-guard when she makes a recruiting visit to an alternative high school overseen by her former college classmate, the freewheeling John Pressman. Pressman has surmised that Jeremiah, his gifted yet very unconventional student, might well be the son that Portia secretly gave up for adoption many years ago.

Angie lives in the Bensonhurst section of Brooklyn, N.Y. and dreams of a better life than everyone she knows. When she finds that she is pregnant by her boyfriend Vinnie, she decides that she will have the baby, but not Vinnie as a husband. This turns the entire neighborhood upside down and starts her on a journey of self discovery. This journey includes her family, a new lover and her life. Even her best friend Tina has trouble understanding Angie. Written by Tony Fontana

Widowed U.S. president Andrew Shepherd, one of the world's most powerful men, can have anything he wants -- and what he covets most is Sydney Ellen Wade, a Washington lobbyist. But Shepherd's attempts at courting her spark wild rumors and decimate his approval ratings.

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.

Naive Midwestern prep student Jonathan bonds with his more worldly roommate, Skip, who takes the small-town boy under his wing. At Skip's urging, the inexperienced Jonathan is emboldened to seek out older women in the cocktail lounges of nearby Chicago, where he meets and beds the alluring Ellen, who unfortunately turns out to be Skip's mother. The division between the friends is further deepened when a cheating scandal engulfs the school.

When Juli meets Bryce in the second grade, she knows it's true love. After spending six years trying to convince Bryce the same, she's ready to give up - until he starts to reconsider.

Fourteen years after the events of the first film, a series of encounters between people in Britain reminds us that in these different times Love, actually exists.

Carolina is a 2003 romantic comedy film directed by Marleen Gorris, starring Julia Stiles, Shirley MacLaine, Alessandro Nivola, Mika Boorem, Randy Quaid, and Jennifer Coolidge. Lisa Sheridan has a cameo role in the film, and Barbara Eden has the uncredited part of Daphne. It is set in Los Angeles, California. Shot in 2003, the film failed to find a distributor and was released direct-to-video in 2005.

Gib, a beer-guzzling slob, and Alison, an uptight Ivy-Leaguer, are an unlikely duo stuck together on a cross-country trip during Christmas break. At first they get on each other's nerves but, as time passes, they find their divergent natures complement each other. Now they need to realize what they've already found before it's too late.

Olive, an average high school student, sees her below-the-radar existence turn around overnight once she decides to use the school's gossip grapevine to advance her social standing. Now her classmates are turning against her and the school board is becoming concerned, including her favorite teacher and the distracted guidance counselor. With the support of her hilariously idiosyncratic parents and a little help from a long-time crush, Olive attempts to take on her notorious new identity and crush the rumor mill once and for all.

It's Hollywood, 1958. Small town beauty queen and devout Baptist virgin Marla Mabrey, under contract to the infamous Howard Hughes, arrives in Los Angeles. At the airport, she meets her driver Frank Forbes, who is engaged to be married to his seventh grade sweetheart and is a deeply religious Methodist. Their instant attraction not only puts their religious convictions to the test, but also defies Hughes' number one rule: No employee is allowed to have any relationship whatsoever with a contract actress. Hughes' behavior intersects with Marla and Frank in very separate and unexpected ways, and as they are drawn deeper into his bizarre world, their values are challenged and their lives are changed.

Rose Morgan, who still lives with her mother, is a professor of Romantic Literature who desperately longs for passion in her life. Gregory Larkin, a mathematics professor, has been burned by passionate relationships and longs for a sexless union based on friendship and respect.

Eddy and Stuart share two-thirds of a dormitory suite. Due to bureaucratic error, a woman named Alex is added to their room. At first, relations among the three are tense. Soon, however, Alex falls for Eddy, and Stuart lusts after Alex.

Back in 1982, a Texas University student who is curious about the male sex fantasies he's been having, decides he needs to hook up with an out gay student on campus.

Music From Another Room is a romantic comedy that follows the exploits of Danny, a young man who grew up believing he was destined to marry the girl he helped deliver as a five year old boy when his neighbor went into emergency labor. Twenty-five years later, Danny returns to his hometown and finds the irresistible Anna Swann but she finds it easy to resist him since she is already engaged to dreamboat Eric, a very practical match. In pursuit of Anna, Danny finds himself entangled with each of the eccentric Swanns including blind, sheltered Nina, cynical sister Karen, big brother Bill and dramatic mother Grace as he fights to prove that fate should never be messed with and passion should never be practical.

An American girl on vacation in Italy finds an unanswered "letter to Juliet" -- one of thousands of missives left at the fictional lover's Verona courtyard, which are typically answered by a the "secretaries of Juliet" -- and she goes on a quest to find the lovers referenced in the letter.

College has always been a time for experimentation, sexual, cultural and otherwise. "Harvard Man" plays out against a background of love, sex, basketball, crime and experimentation. Action and philosophy in young people's quest to discover their true identity.

Dorian realizes he is gay in his final year of high school. He meets another gay youth locally, but remains confused. He starts therapy, then resorts to confession in the Church, and finally comes out to his brother. Dorian then decides to come out to his father; he gets kicked out of the house.

Paper Heart follows Nick and Charlyne on a cross-country journey to document what exactly "love" is. Interviewing ministers, happily married couples, chemists, romance novelists, divorce lawyers, a group of children and more, the determined young girl attempts to find definition and perhaps even experience the mysterious emotion.

When he suddenly finds himself without his long-standing blue-collar job, Larry Crowne enrolls at his local college to start over. There, he becomes part of an eclectic community of students and develops a crush on his teacher.

Jenny Farrell is getting married. But how will her straight-laced family react when they find out that the woman they thought was their daughter’s roommate is actually her fiancée? As the old-fashioned Farrells attempt to come to terms with the prospect of a surprise daughter-in-law, they face a difficult choice: either adapt with the times or risk being left behind.

Two single friends agree to be each others' respective plus one for each wedding they're invited to during a particularly busy nuptial period of their lives.

Antoine and Kenny Tyler are NCAA college basketball players, and Antoine is the star. Suddenly Antoine dies of heart attack and Kenny has to fill his shoes as leader of team. Some time later, Antoine returns as a ghost and helps Kenny in game and in life, but Kenny changes in the process and doesn't quite like it.

A manic-depressive mess of a father tries to win back his wife by attempting to take full responsibility of their two young, spirited daughters, who don't make the overwhelming task any easier.

Seven close friends reunite for the wedding of two of their friends. Problems arise because the bride and the maid of honor have had a long rivalry over the groom.

A sex therapist goes through puberty after the successful removal of a benign tumor resting against his pituitary gland. He experiences all the changes and effects of puberty over a three-week period.

After being cut from the USA softball team and feeling a bit past her prime, Lisa finds herself evaluating her life and in the middle of a love triangle, as a corporate guy in crisis competes with her current, baseball-playing beau.

A conservative lawyer named Diane takes her two teenage children Jake and Zoe to meet their estranged, hippie grandmother in Woodstock after her husband asks for a divorce.

High school student Yuki Hase (Kento Yamazaki) wants to become close with classmate Kaori Fujimiya (Haruna Kawaguchi) who is alway by herself. Kaori Fujimiya refuses to become close with Yuki Hase, because she forgets her friends every new Monday. Even though Kaori tells Yuki why she doesn't want to become friends, Yuki still wants to become close to her.