20 best movies like Playing Mona Lisa (2000)

Social satire based on the best-seller by Adele Lang humorously chronicles the life of Katya Livingston, a self-centered, obnoxious and conceited 28-year-old ad sales exec who won't let anything or anyone stand in her way in getting to the top of the San Francisco social ladder.

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

Jimmie is seeing his single friends get married one by one. He isn't too worried until his girlfriend Anne catches the bouquet at his friend Marco's wedding. Suddenly, his wild mustang days are numbered. He finally decides to propose to her, but he sticks his foot in his mouth and botches the proposal. Being insulted by the defeatist proposal, Anne leaves town on an assignment. After she's gone, he finds out that his recently-deceased grandfather's will stipulates that he gets nothing of a multi-million dollar fortune unless he's married by 6:05pm on his 30th birthday: tomorrow! Not being able to find Anne, Jimmie begins backtracking through his past girlfriends to find a wife.

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.

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.

Altruistic Jane finds herself facing her worst nightmare as her younger sister announces her engagement to the man Jane secretly adores.

Charley Pearl, wealthy heir and gadabout, is slated to marry Adele, the daughter of a Hollywood tycoon. But, during a wild bachelor party in Las Vegas, Charley strikes up a flirtation with nightclub crooner Vicki Anderson that soon leads to her bedroom. When the couple are discovered by Vicki's beau, infamous gangster Bugsy Siegel, he makes a surprising pronouncement -- they'd better marry, or Charley is a dead man.

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.

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.

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.

Christina's love life is stuck in neutral. After years of avoiding the hazards of a meaningful relationship, one night while club-hopping with her girlfriends, she meets Peter, her perfect match. Fed up with playing games, she finally gets the courage to let her guard down and follow her heart, only to discover that Peter has suddenly left town. Accompanied by Courtney, she sets out to capture the one that got away.

A physical therapist falls for the basketball player she is helping recover from a career-threatening injury.

Deloris Van Cartier is again asked to don the nun's habit to help a run-down Catholic school, presided over by Mother Superior. And if trying to reach out to a class full of uninterested students wasn't bad enough, the sisters discover that the school is due to be closed by the unscrupulous chief of a local authority.

This joyous celebration of frontier life combines tender romance and violent passion in the Oklahoma Territory of the 1900s with a timeless score filled with unforgettable songs. Rodgers and Hammerstein's hit Broadway musical.

After a one-night stand a couple is faced with the terrifying possibility of what they really want.

Quirky Jamie Harris is a magnet for less-than-kind men as she hops beds. But things start to look up when she becomes the object of affection of two seemingly normal men. Unfortunately, there's the immense problem of her self-imposed 90-day moratorium on sex.

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.

Ben Holmes, a professional book-jacket blurbologist, is trying to get to Savannah for his wedding. He just barely catches the last plane, but a seagull flies into the engine as the plane is taking off. All later flights are cancelled because of an approaching hurricane, so he is forced to hitch a ride in a Geo Metro with an attractive but eccentric woman named Sara.

Mary Fiore, San Francisco's premiere wedding planner is rescued from an accident by the man of her dreams, pediatrician Steve Edison, only to find he is the fiancé of her latest client, wealthy Fran Donnolly. As Mary continues making the wedding arrangements, she and Steve are put into a string of uncomfortable situations that force them to face their mutual attraction.

A small circle of friends suffering from post-collegiate blues must confront the hard truth about life, love and the pursuit of gainful employment. As they struggle to map out survival guides for the future, the Gen-X quartet soon begins to realize that reality isn't all it's cracked up to be.

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.

Tom and Hannah have been platonic friends for 10 years. He's a serial dater, while she wants marriage but hasn't found Mr. Right. Just as Tom is starting to think that he is relationship material after all, Hannah gets engaged. When she asks Tom to be her 'maid' of honor, he reluctantly agrees just so he can attempt to stop the wedding and woo her.

A washed up golf pro working at a driving range tries to qualify for the US Open in order to win the heart of his succesful rival's girlfriend.

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.

Two strangers meet and fall in love during the weekend that they are planning their respective weddings.

Jeffrey, a gay man living in New York City with an overwhelming fear of contracting AIDS, concludes that being celibate is the only option to protect himself. As fate would have it, shortly after his declaration of a sex-free existence, he meets the handsome Steve Howard, his dream man -- except for his HIV-positive status. Facing this dilemma, Jeffrey turns to his best friend and an outrageous priest for guidance.

A lesbian hires a male escort to break the heart of the bisexual woman who has just dumped her.

A man suspects his girlfriend of being unfaithful. So he sends her a letter, but than finds out that he was wrong. He has 24 hours to stop the package, prevent a disaster, and fall in love. The only problem is the delivery man will not stop until the package has been delivered.

Standing on the precipice of adulthood, a group of friends navigate new relationships, while reexamining others, during their final summer before college.

The Malacicis, a hard-working Italian family recently immigrated from Florence, open a fancy restaurant in the Bronx, N.Y., drawing the ire of another clan. Mike and Sadie Capomezzo, equally hard-working Sicilian caterers from the area, find they cannot stand Piero and Maria Malacici. But things get complicated when the Malacicis' daughter, Gina, and the Capomezzos' son, Rosario, fall in love.

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.

A small town girl and a city boy meet on the Sunset Strip, while pursuing their Hollywood dreams.

An aloof, struggling food photographer thinks he has found true love with a fiery grade-school teacher. At first, the relationship is all wine and roses, but as they realize they have little in common besides great sex, the romance wanes, and they struggle through a succession of break-ups and reunions as they try to work things out.

Set to the intoxicating rhythms of Brazil, "Woman on Top" is a spicy, sexy comedy about the magic of food, love and music. Meet Isabella, a sultry enchantress born with the special gift of melting the palates and hearts of men everywhere. When she decides to break free from her rocky marriage and the stifling kitchen of her husband's restaurant in Brazil, she spirits off to San Francisco in pursuit of her dreams of a real culinary career.

A childhood incident has convinced Faith Corvatch that her true love is a guy named "Damon Bradley," but she has yet to meet him. Preparing to settle down and marry a foot doctor, Faith impulsively flies to Venice when it seems that she may be able to finally encounter the man of her dreams. Instead, she meets the charming Peter Wright. But can they fall in love if she still believes that she is intended to be with someone else?

Teenager Jones has opted not to go to college and is instead renting a room in a boarding house to work on his writing skills. Soon, Jones finds himself dividing his time between two women: a young actress named Lisa and a photographer named Jane. After Jane's ex-boyfriend arrives to help her recover from a car accident, Jones begins to understand just how much he cares for her.

A contemporary romantic comedy exploring the unlikely pairing of two 20-somethings thrown together by their respective best friends in hopes of igniting their own romance.

On a university scholarship, a good natured student from the midwest gets a crash course in city life while dealing with three evil roommates. He befriends a virtually homeless college student whom he falls for, but she's dating a nasty professor.

Developed from a radio program which began in 1941, hyperactive teenager Judy challenges and is challeged by her overly proper parents, pest of a brother Randolph and boyfriend Oogie.

After her husband, Carl, suddenly leaves, Joline travels from New York to Texas to track him down. Although Joline tries to remain upbeat, she is discouraged when she discovers that Carl already has a new girlfriend, the lovely Carmen. Familiarizing herself with Carl's new home and friends, Joline gets company in the form of her brother, Jay. Will Joline win Carl back, or are there other romantic possibilities on her horizon?

For 16 years Miss Bentley has been spending April at an elegant hillside villa on Lake Como. This year, 1937, her London society artist father has recently died and the only other English-speaking guests are brash Americans. Then Major Wilshaw arrives. He suggests they meet for cocktails and Miss Bentley stands him up -- not even thinking about it -- as she helps the new nanny of an Italian family settle in. Miss Beaumont, a tall, young American who has dropped out of finishing school in Switzerland, is bored and finds some amusement in flirting with the major, whose libido is awakened for the first time since before the great war. And Miss Bentley now finds more about the major to admire than his ears.

Exactly one year after Tom meets Violet, he surprises her with a wedding ring. By all accounts, Tom and Violet are destined for their happily ever after. However, this engaged couple just keep getting tripped up on the long walk down the aisle.

Childhood friends Tracy Lord and C.K. Dexter Haven got married and quickly divorced. Now Tracy is about to marry again, this time to a shrewd social-climbing businessman. C.K. still loves her. Spy magazine blackmails Tracy's family by threatening to reveal her playboy father's exploits if not allowed to cover the wedding.

How important is the truth when falling in love? Bella is a Manhattan café waitress, about to turn 35, stuck in a long-term affair going nowhere. Paul is a widower, facing old age alone. Bella's mother sets her up with Bruno, a novelist/cabbie who likes to bed-hop and whose ex-wife expects their two children to stay with him for awhile. While Bruno learns some maturity from his young daughter, Paul answers a personals ad placed by a "widow, 60." The two couples - along with one of Paul's older pals and a Jungian stripper - sort out how to initiate a relationship these days, what to do when someone you like disappoints you, and when to tell the truth.

A working girl from New Jersey looks for love with a fast-lane Manhattan salesman from Queens.

Through good times and bad, Stella and Delilah have always had each other. Now, Stella's so busy building a life that she's forgotten how to really live. But Delilah is about to change all that. What starts as a quick trip to Jamaica, end as an exhilarating voyage of self discovery as Stella learns to open her heart and find love - even if it's with a man 20 years her junior.

Still reeling from his breakup with college sweetheart Allison, Adam's world is thrown into further chaos when he’s surprisingly invited to attend her wedding.

New York City. Melvin Udall, a cranky, bigoted, obsessive-compulsive writer, finds his life turned upside down when neighboring gay artist Simon is hospitalized and his dog is entrusted to Melvin. In addition, Carol, the only waitress who will tolerate him, must leave work to care for her sick son, making it impossible for Melvin to eat breakfast.

Described as "90210 on acid", the film tells the story of a day in the lives of a group of high school kids in Los Angeles and the strange lives they lead.

No sooner does Italian-American widow Loretta accept a marriage proposal from her doltish boyfriend, Johnny, than she finds herself falling for his younger brother, Ronny. She tries to resist, but Ronny lost his hand in an accident he blames on his brother, and has no scruples about aggressively pursuing her while Johnny is out of the country. As Loretta falls deeper in love, she comes to learn that she's not the only one in her family with a secret romance.