20 best movies like The Wedding Singer (1998)

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 love story built on a misunderstanding. A transit worker pulls commuter Peter off the 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.

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.

Though Rachel (Ginnifer Goodwin) is a successful attorney and a loyal, generous friend, she is still single. After one drink too many at her 30th-birthday celebration, Rachel unexpectedly falls into bed with her longtime crush, Dex -- who happens to be engaged to her best friend, Darcy (Kate Hudson). Ramifications of the liaison threaten to destroy the women's lifelong friendship, while Ethan (John Krasinski), Rachel's confidant, harbors a potentially explosive secret of his own.

Sidney is a writer who's just left her L.A. Times music review gig to edit New York hip-hop magazine XXL. Dre is an executive with a hip-hop record company based in New York. They've known each other since they met as children, when both discovered hip-hop for the first time. Now that they're back together, they should be perfect for each other, except that Dre's about to marry lawyer Reese and Sidney claims not to be interested in Dre romantically. Meanwhile, Dre is growing increasingly restless with his company's focus on profit over artistry, which leads to signing the gimmicky duo Ren and Ten while ignoring the talented Chris

During their travels from Chicago to New York, Harry and Sally Will debate whether or not sex ruins a perfect relationship between a man and a woman. Eleven years later, and they're still no closer to finding the answer.

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.

Book superstore magnate, Joe Fox and independent book shop owner, Kathleen Kelly fall in love in the anonymity of the Internet – both blissfully unaware that he's putting her out of business.

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.

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.

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

Nora Wilder (Parker Posey), a single, career woman works at a Manhattan boutique hotel where her excellent skills in guest relations lack in the romantic department. If it is not her loving and dominant mother (Gena Rowlands) attempting to set her up that consistently fail, she has her friend’s (Drea de Matteo) disastrous blind dates to rely on as a backup for further dismay. She's surrounded by friends who are all happily engaged or romantically involved and somehow, love escapes Nora -- until she meets an unusual Frenchman (Melvil Poupaud) who helps her discover life beyond her self-imposed boundaries.

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.

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 woman on the brink of a marriage proposal is told by a friend that she should date other men before spending the rest of her life with her boyfriend.

Celeste and Jesse met in high school and got married young. They laugh at the same jokes and finish each other’s sentences. They are forever linked in their friends’ minds as the perfect couple – she, a high-powered businesswoman and budding novelist; he, a free spirit who keeps things from getting boring. Their only problem is that they have decided to get divorced. Can their perfect relationship withstand this minor setback?

The "black sheep" son of a wealthy family meets a young psychiatric patient who's been raised in isolation her entire life. He takes the naive young woman home for his brother's wedding an improbable romance blooms, as she impresses everyone with her genuine, simple charms. Remake of the German film "Barfuss" (2005).

When new kid in town Ed Wallis is given an assignment to interview an older person, he turns to his mysterious neighbor, Ashby Holt for help. That new connection leads to unexpected journeys for both of them, as Ashby – who turns out to be a retired CIA assassin – deals with a terminal prognosis, and Ed deals with adjusting to life with his newly single mom and developing relationship with a brainy classmate, Eloise.

A young working girl with a blue-collar background is surprised when her new fiancé announces he is actually a prince of a small sovereign country in Europe. After the couple quickly takes off to spend the holidays at his family’s sprawling, royal castle, she must work hard to win over her disapproving and unaccepting future mother-in-law—the Queen—and find out if love truly can conquer all.

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.

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 woman at rock bottom must find her way across Los Angeles in order to crash her ex-boyfriend's engagement party.

Family friends Sam and Kat spend every Christmas Eve at the Children's Table. They grow up together, sharing the highs and lows of young adulthood. And at thirty, Sam realizes that Kat is the one...but he's afraid that the past will get in the way.

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.

On a flight from Los Angeles to New York, Oliver and Emily make a connection, only to decide that they are poorly suited to be together. Over the next seven years, however, they are reunited time and time again, they go from being acquaintances to close friends to ... lovers?

When Johnny is released from prison following a forgery charge, he quickly lands a job as a short-order cook at a New York diner. Following a brief fling with waitress Cora, Frankie develops an attraction for Cora's friend and fellow waitress Frankie. While Frankie resists Johnny's charms initially, she eventually relents when her best friend, Tim, persuades her to give Johnny a chance.

Nino is a quiet outcast with only a bird for a friend. Kira is a popular boy with a big secret. Even though they live next to each other, they have never spoken. But when Nino learns Kira's secret, everything begins to change, and what starts as a hesitant friendship grows into something more... but how long can it last?

Two women, one (Cameron Diaz) from America and one (Kate Winslet) from Britain, swap homes at Christmastime after bad breakups with their boyfriends. Each woman finds romance with a local man (Jude Law, Jack Black) but realizes that the imminent return home may end the relationship.

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.

A couple fall in love despite the girl's pessimistic outlook. As they struggle to come to terms with their relationship, something supernatural happens that tests it.

Annie is stuck in a long-term relationship with Duncan – an obsessive fan of obscure rocker Tucker Crowe. When the acoustic demo of Tucker's hit record from 25 years ago surfaces, its discovery leads to a life-changing encounter with the elusive rocker himself.

Cheated on, mistreated and stepped on, the women are holding their breath, waiting for the elusive "good man" to break a string of less-than-stellar lovers. Friends and confidants Vannah, Bernie, Glo and Robin talk it all out, determined to find a better way to breathe.

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.

Mickey Gordon is a basketball referee who travels to France to bury his father. Ellen Andrews is an American living in Paris who works for the airline he flies on. They meet and fall in love, but their relationship goes through many difficult patches.

In this world, there are many people who seem to be wandering along a relationship border-lining 'friends' and 'lovers'. This borderline is also commonly known as the FRIEND ZONE. It is a special area for those who are stuck in the middle where they cannot really stay friends with their close friends, nor move forward to be their friends' lovers.

When Elliot, a brash 23-year-old living carefree in New York City, meets the sensible Mia and receives a damning diagnosis all in the same week, his world is turned completely upside down. But as their love blossoms amidst the chaos of his treatment, they discover that Elliot's illness is not the real test of their relationship – it's everything else.

It's an hour before Lucy's wedding and her best friend wants to hear all about what led up to that moment. So, Lucy tells about the five men she had blind dates with over the past year (Doug, Gabriel, Bobby, Barry, and Luke) and her experiences with each one. But which one of the five men is Lucy about to walk down the aisle with?

Kristin has just had to close her small Manhattan clothing boutique to return to her Ohio home town and live in her parents' former home. It's an adjustment for Kristin and her young daughter— especially when she runs into her former high school rival. Kristen and Emily struggle to find their new normal with the help of the hunky local music teacher.

In an attempt to win back her ex-boyfriend on Christmas Eve, Kate ends up ruining her blind date with Miles, a handsome guy she's been set up with. In a strange twist of fate, Kate is given the chance to re-live Christmas Eve twelve times.

Life has its downs for James, living with his mom in Chicago at 39, an aging performer at Second City, eating and weighing too much. A woman he's been dating drops him, as does his agent, her brother. James turns down roles in local TV, roles that make him sad. Someone's remaking his favorite movie, "Marty," a role he'd love, but he doesn't even get an audition.

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.

After an extremely regrettable one night stand, two strangers wake up to find themselves snowed in after sleeping through a blizzard that put all of Manhattan on ice. They're now trapped together in a tiny apartment, forced to get to know each other way more than any one night stand should.

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.

Lizzie, a high-end event planner, lies awake nightly while her devoted fiancé Josh rests peacefully. When a sleep-deprived incident causes her to run into Billy, a low-key bartender who is just as sleepless and frustrated as she is, they discover that they can only fall asleep while next to each other.

Reunited after 15 years, famous chef Sasha and hometown musician Marcus feel the old sparks of attraction but struggle to adapt to each other's worlds.

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.

Sam and Gray are such a well-matched pair that it is difficult to believe they are brother and sister rather than husband and wife. They both share a love of 1940s movies and dancing, and when they meet Charlie, they have something else in common: They both fall in love with her. Sam must deal with unexpected feelings of jealousy, while Gray struggles to come to terms with her sexual orientation.

Ex-football star Mike Gambril meets Terry McKay on a flight to Sydney, which is forced to land on a small atoll. They become romantic on board a ship sent to take them to a larger island. They agree to meet in New York three months later to see if the attraction is real. One shows up but the other doesn't. However, a chance meeting brings them together again.

A group of friends reunite ten years after their high-school graduation.

Mandy Moore stars as Halley, a young hip high school student who's 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.