Best movies like Mrs. Winterbourne

The story of a girl who is going from filthy to rich

A unique, carefully handpicked, selection of the best movies like Mrs. Winterbourne Starring Shirley MacLaine, Ricki Lake, Brendan Fraser, Miguel Sandoval, and more. If you liked Mrs. Winterbourne then you may also like: 3 Men and a Little Lady, Three to Tango, A Walk in the Clouds, The Wedding Date, Where the Heart Is 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.

Connie Doyle is eighteen, pregnant and alone. She accidentally ends up on a train where she meets Hugh Winterbourne and his wife pregnant Patricia. The train wrecks and she wakes up in the hospital to find out that it's been assumed that she's Patricia. Hugh's mother takes her in and she falls in love with Hugh's brother Bill. Just when she thinks everything is going her way, her ex-boyfriend shows up.

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3 Men and a Little Lady

Sylvia's work increasingly takes her away from the three men who help bring up Mary, her daughter. When she decides to move to England and take Mary with her, the three men are heartbroken at losing the two most important females in their lives.

Three to Tango

Oscar and Peter land a career-making opportunity when a Chicago tycoon chooses them to compete for the design of a cultural center. The tycoon mistakenly believes that Oscar is gay and has him spy on his mistress Amy. Oscar goes along with it and ends up falling in love with Amy.

A Walk in the Clouds

World War II vet Paul Sutton falls for a pregnant and unwed woman who persuades him -- during their first encounter -- to pose as her husband so she can face her family.

The Wedding Date

With the wedding of her younger sister fast approaching, Kat Ellis faces the undesirable prospect of traveling alone to London for the ceremony. While this is bad enough, Jeffrey, the man who left her as they moved closer to marriage, happens to be the groom's best man. Determined to show everyone -- most of all Jeffrey -- that her romantic life is as full and thrilling as ever, Kat hires a charming male escort as her date.

Where the Heart Is

Novalee Nation is a 17-year-old Tennessee transient who has to grow up in a hurry when she's left pregnant and abandoned by her boyfriend on a roadside, and takes refuge in the friendly aisles of Wal-Mart. Eventually, some eccentric but kindly strangers 'adopt' Novalee and her infant daughter, helping them buck the odds and build a new life.

While You Were Sleeping

A transit worker pulls commuter Peter off railway tracks after he's mugged, but—while he's in a coma—his family mistakenly thinks she's Peter's fiancée, and she doesn't correct them. Things get more complicated when she falls for his brother, who's not quite sure that she's who she claims to be.

Once Around

Renata Bella feels like a failure at life and career. But when Renata attends a seminar on selling real estate, she finally finds True Love. Sam Sharpe, while a top-notch, successful salesman, is much older than Renata. She is swept away by his excessively flamboyant style and irrepressible nature. The very traits she finds romantic, however, lead to repeated conflict with her family, especially her beloved father Joe, leaving Renata trapped in the middle.

Only the Lonely

Danny Muldoon, a Chicago policeman, still lives with his overbearing mother Rose. He meets and falls in love with Theresa Luna , whose father owns the local funeral parlour. Naturally, his mother objects to the relationship, and Danny and Theresa must either overcome her objections or give up the romance.

The Other Sister

A mentally challenged girl proves herself to be every bit as capable as her "perfect" sister when she moves into an apartment and begins going to college.

Overboard

Heiress Joanna Stayton hires carpenter Dean Proffitt to build a closet on her yacht—and refuses to pay him for the project when it's done. But after Joanna accidentally falls overboard and loses her memory, Dean sees an opportunity to get even.

Raising Helen

Helen Harris has a glamorous, big-city life working for one of New York's hottest modeling agencies. But suddenly her free-spirited life gets turned upside down when she must chose between the life she's always loved, and the new loves of her life!

The Back-Up Plan

When Zoe tires of looking for Mr. Right, she decides to have a baby on her own. But on the day she's artificially inseminated, she meets Stan, who seems to be just who she's been searching for all her life. Now, Zoe has to figure out how to make her two life's dreams fit with each other.

Crush

Three 40-something women in a small English town meet weekly for a ritual of gin, cigarettes, and sweets -- and swapped stories arguing which of them has the most pathetic love life. Kate is headmistress at the local school; her best friends are the town's police chief and a cynical, thrice-divorced doctor.

Sabrina

An ugly duckling having undergone a remarkable change, still harbors feelings for her crush: a carefree playboy, but not before his business-focused brother has something to say about it.

Kimberly

Four young men fall in love with the same woman. When they all find themselves attracted by Kimberly, hey vow not to fight for her affections during the season -- but then she gets pregnant and doesn't know which teammate is the father.

Hope Floats

Birdee Pruitt has been humiliated on live television by her best friend, Connie, who's been sleeping with Birdee's husband, Bill. Birdee tries starting over with her daughter, Bernice, by returning to her small Texas hometown, but she's faced with petty old acquaintances who are thrilled to see Birdee unhappy -- except for her friend Justin. As he helps Birdee get back on her feet, love begins to blossom.

Home Fries

Dorian and Angus chase down their womanizing stepfather with a helicopter, frightening him to death. In his effort to cover their tracks, Dorian begins investigating his stepfather's mistress, Sally. She works at a fast-food drive-through, she's pregnant and Dorian quickly falls in love with her. Unfortunately, his scheming mother wants Sally dead. And Sally isn't sure she wants Dorian to be her child's father and also his brother.

How to Deal

Halley is convinced true love doesn't exist based on the crazy relationships around her. Her mother is divorcing her father who is dating a younger woman Halley can't stand. Her crazed sister is planning a wedding but has second thoughts and her best friend has fallen madly in love for the first time leaving Halley to feel even more alone.

Picture Perfect

A young advertising executive's life becomes increasingly complicated when, in order to impress her boss, she pretends to be engaged to a man she has just met.

The Proposal

When she learns she's in danger of losing her visa status and being deported, overbearing book editor Margaret Tate forces her put-upon assistant, Andrew Paxton, to marry her.

The Truth About Cats & Dogs

A successful veterinarian and radio show host with low self-esteem asks her model friend to impersonate her when a handsome man wants to see her.

Nine Months

When he finds out his longtime girlfriend is pregnant, a commitment-phobe realizes he might have to change his lifestyle for better or much, much worse.

Time Share

Two single parents - male and female - along with their kids have to involuntarily share a house for their holidays.

Kissing Cousins

A "relatively" romantic comedy about a professional heartbreaker (and cynical bachelor) who teams up with his attractive cousin from the UK in order to fool his friends into believing he is capable of a relationship. Hijinks and laughs ensue with a hilarious cast!

Fools Rush In

After a one night stand with Alex, Isabel realizes that she is pregnant and they decide to get married. However, along with the marriage comes compromise of one's own cultural traditions.

Love Comes Softly

Marty is a 19 year old pioneer woman, recently married. She goes west with her husband Clem, hoping to start a new life. But Clem unexpectedly dies, and Marty finds herself alone, two months pregnant. Clark Davis, a widower, offers her a marriage of convenience: she needs food and money, and he needs someone to take care of his daughter Missie. She accepts his proposal as a temporary solution.

Betting On The Bride

A womanizer bets that he can get someone to accept his marriage proposal after dating them for just 30 days. What he doesn't know is that the woman he targeted has some serious commitment issues.

Lovestruck: The Musical

Harper was one of the best dancers to hit Broadway, but an injury caused her to leave the spotlight, become a choreographer, and raise her daughter Mirabella. When Mirabella decides to quit the show to get married, her mother is determined to put a stop to the wedding and show Mirabella that she cannot give up her career for love.

6.7 / 10 2008 Comedy Romance
suggested by: cosmicvoyage

My Sassy Girl

A guy has his life planned out until he is wooed, groomed and then dumped by an elusive woman.

Destination Wedding

Ellie Hamilton is helping plan her little sister’s wedding taking place in Acapulco. With the nuptials just a few days away—and no sign yet of the bride and groom—Ellie must work with her ex-boyfriend to make last minute decisions and stall worried family and guests.

Stop the Wedding

A meddling man and woman determined to stop a wedding for the good of the bride and groom instead wind up falling in love with each other.

A Christmas Wedding Date

After being fired, Rebecca hours back to her old home town to attend her friends wedding on Christmas Eve and visit her mother. But when she tries to return home she finds she must relive Christmas Eve over and over until she gets it right.

Straight From the Heart

Jordan Donavan, a photographer in New York, is so disappointed when after five years of going steady Edward Morgan offers her not marriage but just to move in with him, that she accepts the match-making arranged via a magazine by her female friend with Tyler Ross, a horse rancher in the West, whose candidacy was actually also posted by his sister. After a bad start they soon grow closer.

Suzanne's Diary for Nicholas

A woman discovers the truth about her former lover from the diary that his first wife wrote to their son, Nicholas.

A Wedding Wonderland

When family conflicts arise between happy couple Hallie and Lucas on the week before their big day, their plans for a breezy wedding in the tropics take a turn and their love is tested when they are forced to put on a small town winter wedding in the snow.

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