20 best movies like Taking Chances (2009)

Drew Baylor is fired after causing his shoe company to lose hundreds of millions of dollars. To make matters worse, he's also dumped by his girlfriend. On the verge of ending it all, Drew gets a new lease on life when he returns to his family's small Kentucky hometown after his father dies. Along the way, he meets a flight attendant with whom he falls in love.

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.

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.

After her sister and brother-in-law's tragic death, an American woman who is the guardian for her young niece and nephew is invited to a royal European castle for Christmas by her late brother-in-law's father, the Duke of Castlebury. Feeling out of place as a commoner, she is determined to give her family a merry Christmas and surprises herself when she falls for a handsome prince.

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.

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.

Left broke and homeless by his wealthy parents' divorce, a young man moves in with an old friend and finally meets the woman of his dreams -- only to discover she's already dating his friend.

A washed up Vegas lounge singer, Jack Satin (Hamilton von Watts), has no money, no job, and delusional aspirations of fame. When Jack is forced to leave Vegas, he packs up his old Cadillac and hits the road for Atlantic City. But his car dies in the desert and Jack is left stranded in the small town of Lost Springs. There, Jack meets jazz legend turned mechanic, Doc Bishop (Robert Guillaume), who helps him with his car trouble. Although Jack is far from the stage, he begins to find himself feeling at home in the small town. When he meets local bar owner, Lauren Wells (Melissa Joan Hart), Jack starts to see there is more to life than chasing fame and fortune. Doc encourages Jack to explore his true love of music, while Lauren provides the audience he has always wanted. But as Jack realizes this town has more to offer him than the bright lights of the big city, his Vegas past catches up with him -- what unfolds is comedy at the crossroads of life.

When her rather explicit copy is rejected, magazine journalist Kate is asked by her editor to come up with an article on loving relationships instead, and to do so by the end of the day. This gets Kate thinking back over her own various experiences, and to wondering if she is in much of a position to write on the subject.

Aged, embittered widower, Fred learns to enjoy life thanks to his elderly yet vibrant neighbor, Elsa. Upon learning Elsa is terminally ill, Fred takes her to the Fontana di Trevi in Rome in order to reenact her favorite scene from ‘La Dolce Vita’.

A Hollywood-set romantic tale of a guy who is content to live his life without a job yet with the love of his life, a young actress.

When they say “love is blind” they must have been talking about Amy and Ben. Amy is a beautiful young woman with a mysterious past. Ben is a scruffy slacker, whose only ambition seems to be avoiding growing up. However, Amy sees something in Ben that Ben doesn't see in himself, which gives Ben the confidence to make something of his life. The power of love shows Ben that being a grown-up isn't such a bad thing after all.

Pressured by his deceased mother's ghost to return home to the family he abandoned, a former addict grabs a bag of pills and a sack of marijuana and hits the road to Shreveport.

A man, shaken by fate after his wife's death, chooses to be a monk.

Big city girls Julia and her best friend Sydney take a trip to a dude ranch in Wyoming for a fun weekend getaway, but after a brawl at the local bar, the girls are sentenced to stay in town and perform community service. Along the way, Julia finds love and her true calling in life.

Hamo, a handsome 60-year old man, lives alone in a Romenian village with one of his daughters and his granddaughter. He also owns a retirement of seven dollars per month, a closet, an old russian television set and a military costume.A letter from his second daughter arrives from France.A rumor runs through the village: the envelope would be full of money...But Hamo doesn't think but of the beautiful unknown girl from the cemetery.

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.

Set to the music of popular hit songs from the 1980s. A beautiful coastal village, present day Italy. After a whirlwind romance, Maddie is preparing to marry gorgeous Italian Raf, and has invited her sister Taylor to the wedding. Unbeknownst to Maddie, however, Raf is Taylor's ex-holiday flame, and the love of her life...

Travis and Gabby first meet as neighbors in a small coastal town and wind up in a relationship that is tested by life's most defining events.

A decade after they graduated from high school and went their separate ways, Casper (Sam Rosen), a soldier haunted by the horrors of war, and Rebecca (Zoe Lister Jones), a whip-smart graduate student with a shaky future, reunite by chance and get to know each other over the course of an accidental tour of the little-known underbelly of Minneapolis. The evening's odyssey includes a bar fight, a house party, a punk-rock circus, a spontaneous burglary, a home Casper did not know he had, and a cast of strange characters, unexpected allies and disappointing friends.

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.

Duets is a road-trip comedy which revolves around the little known world of karaoke and the whimsical characters who inhabit it. All roads lead to Omaha, site of a national karaoke competition where this motley group of singers and stars come together for a blow-out sing-off.

A love story about a woman who "just wants someone who makes her laugh" and a man who is not that funny. As he tries to learn how to be the man she says she wants, they each find an unexpected chance at happiness.

Businessman Wesley Deeds is jolted out of his scripted life when he meets Lindsey, a single mother who works on the cleaning crew in his office building.

Amy, a naive college graduate who believes she's destined to be a great poet, begrudgingly accepts a job at a sex shop while she pursues a mentorship with reclusive writer Rat Billings.

Ivy League Freshman, Aaron Milton (17) gets a different kind of education when he falls for Linda (34) a vivacious former wild-child who has returned to college to straighten out her life. The curriculum gets more challenging when Aaron meets Linda's sarcastic 14 year-old daughter, Beth - who quickly develops a crush on him. The math doesn't work in either direction but the dysfunctional triangle becomes a learning experience for all involved.

A childless couple bury a box in their backyard, containing all of their wishes for an infant. Soon, a child is born, though Timothy Green is not all that he appears.

After a distastrous first date for caterer Holly and network sports director Messer, all they have is common is a dislike for each other and their love for their goddaughter Sophie. But when they suddenly become all Sophie has in this world, Holly and Messer must set their differences aside. Juggling careers and social calendars, they'll have to find common ground while living under the same roof.

A two days from the life of Pyotr Drozdov, a highly ranked official from Moscow, which he spends with young museum employee Masha.

Ren MacCormack is transplanted from Boston to the small southern town of Bomont where loud music and dancing are prohibited. Not one to bow to the status quo, Ren challenges the ban, revitalizing the town and falling in love with the minister’s troubled daughter Ariel in the process.

When a college piano prodigy tries to check his mother into rehab, he is taken hostage by her drug dealer and swept along on a wild adventure.

Single mother Ryan has just about given up on dating after her divorce, happily accepting her young son as the most important man in her life. That all changes when Ryan's brother Owen, also feeling unlucky in love after a bad breakup, swaps his home in their small North Carolina town with New York City adman Sean.

Pompous and self-absorbed Kyle, is unhappily stuck in his life, longing to relive the success of his first novel. His not-so-desirable life rapidly unravels forcing him to return home to his wildly eccentric family with his tail between his legs. Life at home begins to show signs of improvement when Kyle meets the spunky, vivacious girl across the street who recruits Kyle to help her make the world a better place, making him feel alive for the first time in ages and inspiring his writing. But its short-lived. Joys been told shes going to die soon and wants Kyle to write her obituary.

After spending eight months in a mental institution, a former teacher moves back in with his parents and tries to reconcile with his ex-wife.

A family dog—with a near-human soul and a philosopher's mind—evaluates his life through the lessons learned by his human owner, a race-car driver.

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).

A long-time married couple who've spent their lives together in the same New York apartment become overwhelmed by personal and real estate-related issues when they plan to move away.

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.

The film follows Grace, a young woman whose irresponsible mother blows her college fund on her younger sister's beauty pageant campaign.

On a small town college campus, a philosophy professor in existential crisis gives his life new purpose when he enters into a relationship with his student.

Miss Meadows is a school teacher with impeccable manners and grace. However, underneath the candy-sweet exterior hides a ruthless gun-toting vigilante who takes it upon herself to right the wrongs in the world by whatever means necessary. For Miss Meadows, bad behavior is simply unforgivable.

Ivana Cornejo is just getting used to being single again after her divorce three years ago. After an exasperating call from her ex-husband, she throws her cell phone away. Fortunately, the man who finds it calls her to return it, and to her amusement they have an instant rapport. The man on the other end of the phone is León Godoy, a renowned architect with a charming voice and a charismatic personality. They schedule a date so that he can return the cell phone. When León arrives, Ivana is surprised: he is everything she had imagined, except for one unexpected and startling detail... he’s only 4'5" tall.

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 dark comedy which follows two brothers who are in love with the same woman.

A small town girl is caught between dead-end jobs. A high-profile, successful man becomes wheelchair bound following an accident. The man decides his life is not worth living until the girl is hired for six months to be his new caretaker. Worlds apart and trapped together by circumstance, the two get off to a rocky start. But the girl becomes determined to prove to the man that life is worth living and as they embark on a series of adventures together, each finds their world changing in ways neither of them could begin to imagine.

Marisa Ventura is a struggling single mom who works at a posh Manhattan hotel and dreams of a better life for her and her young son. One fateful day, hotel guest and senatorial candidate Christopher Marshall meets Marisa and mistakes her for a wealthy socialite. After an enchanting evening together, the two fall madly in love. But when Marisa's true identity is revealed, issues of class and social status threaten to separate them. Can two people from very different worlds overcome their differences and live happily ever after?

Hum Tum (Hindi: हम तुम, translation: You and Me, Urdu: ہم تم) is a Bollywood movie, released in India on May 28, 2004, directed by Kunal Kohli and produced by Aditya Chopra and Yash Chopra. The movie stars Saif Ali Khan and Rani Mukerji in the lead roles.

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.

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

Simon Birch and Joe Wenteworth are boys who have a reputation for being oddballs. Joe never knew his father, and his mother, Rebecca, is keeping her lips sealed no matter how much he protests. Simon, meanwhile, is an 11-year-old dwarf whose outsize personality belies his small stature. Indeed, he often assails the local reverend with thorny theological questions and joins Joe on his quest to find his biological father.