20 best movies like You, Me and Dupree (2006)

Thirty-five years in the life of Max, his best friend Sal and a woman they both adore, Lyla. The trio stumble through mandatory but seemingly unfulfilling entanglements, at weddings, funerals, hospitals, eateries, divorce courts and the tool shed. A deadpan fable about time sneaking up on and swerving right around us.

A romantic comedy that brings together three disparate characters who are learning to face a challenging and often confusing world as they struggle together against a common demon: sex addiction.

Following a wild night out with his Best Man, Rob Anderson wakes up to find himself naked in an elevator on the morning of his wedding day and is forced to relive the morning over and over again.

All the couples are back for a wedding in Las Vegas, but plans for a romantic weekend go awry when their various misadventures get them into some compromising situations that threaten to derail the big event.

Eddie, the 40-year-old confirmed bachelor finally says "I do" to the beautiful and sexy Lila. But during their honeymoon in Mexico, the woman of his dreams turns out to be a total nightmare, and the guy who could never pull the trigger realizes he’s jumped the gun.

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).

Revolves around three friends who have dream weddings only to find out that the pastor who married them failed to complete the key paperwork required to make them official.

Patrick returns to San Francisco for the first time in almost a year to celebrate a momentous event with his old friends. In the process, he must face the unresolved relationships he left behind and make difficult choices about what’s important to him.

Smitten with a Jewish woman, a gentile asks his Jewish pal to advise him on how to act like a member of the community.

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.

"Cavemen" is a comedic film with a slight edge of drama revolving around the lives of somewhat single, somewhat unemployed guys living in a warehouse converted to living quarters in the 'Arts District' of Downtown Los Angeles, California they are toiling adulthood and realities of love.

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.

Aspiring New York City artist, John Hollar returns to his Middle America hometown on the eve of his mother’s brain surgery. Joined by his girlfriend, eight months pregnant with their first child, John is forced to navigate the crazy world he left behind.

Newly engaged, Ben and Sadie can't wait to start their life together and live happily ever after. However Sadie's family church's Reverend Frank won't bless their union until they pass his patented, "foolproof" marriage prep course consisting of outrageous classes, outlandish homework assignments and some outright invasion of privacy.

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.

Four lifelong friends have their lives forever changed after reading Fifty Shades of Grey in their monthly book club.

'Divorce Invitation' centers on Mike Christian, a happily married man who runs into his high school sweetheart Alex, and after all these years, sparks still fly. When Mike is determined Alex is his true soul mate, he realizes he has a huge problem-he signed an iron-clad pre-nuptial agreement and his wife will not let him out of the marriage

In a world connected by YouTube, iTunes, and Facebook, Lola and her friends navigate the peer pressures of high school romance and friendship while dodging their sometimes overbearing and confused parents. When Lola's mom, Anne, "accidentally" reads her teenage daughter's racy journal, she realizes just how wide their communication gap has grown.

Jamie is a New York-based executive recruiter who entices Dylan, an art director from Los Angeles, to take a job at the New York office of GQ magazine. Finding that they have much in common, the two become fast friends. Feeling jaded by a number of broken romances, Dylan and Jamie decide that they are ready to quit looking for true love and focus on having fun. However, complications unfold when the two best pals add sex to their relationship.

Eddie lands his first teaching gig at an inner city middle school and finds his highly pubescent pupils are receiving no form of sexual education. Eddie isn't really equipped to teach them...he's not exactly experienced romantically.

Iris invites her friend Jack to stay at her family's island getaway after the death of his brother. At their remote cabin, Jack's drunken encounter with Hannah, Iris' sister, kicks off a revealing stretch of days.

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.

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.

Three friends are asked to be bridesmaids at a wedding of a woman they used to ridicule back in high school.

During a wild vacation in Las Vegas, career woman Joy McNally and playboy Jack Fuller come to the sober realization that they have married each other after a night of drunken abandon. They are then compelled, for legal reasons, to live life as a couple for a limited period of time. At stake is a large amount of money.

Phil's new phone comes with an unexpected feature, Jexi...an A.I. determined to keep him all to herself in a comedy about what can happen when you love your phone more than all else.

A woman struggles to escape the clutches of her overbearing, co-dependent mother, while gradually falling for a sexy, sophisticated attorney.

A chain reaction of confrontations and romantic encounters occurs when college friends reunite for one's wedding.

A group of 30-year-olds who have been friends since high school attempt to throw an end-of-summer orgy.

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

When a professional couple, who have lived and worked together for many years, finally decide to marry, their sudden betrothal causes many unexpected difficulties. They soon find that being married is often quite different from being "best friends."

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.

After fast-paced New York City high-end real estate broker Fiona Rangely (Lacey Chabert) gets dumped by her boyfriend, she escapes to her family’s quaint Vermont Inn for a few days to slow down and evaluate her life. When her ex-boyfriend Nate shows up at the Inn with a brand new girlfriend, Fiona quickly devises a plan to win him back: pretend the handsome and very laid- back head chef Derek (Carlo Marks) is her new boyfriend! Much to the surprise of Derek --and to Fiona herself-- in pretending to be in love, she realizes that she’s been thrown a curveball: sometimes the best things in life are worth the wait.

Terrence J. stars as Charlie, a playboy who's convinced that relationships are dead. His two best friends, Donald Faison and Robert C. Riley, bet him that if he sticks to one woman for one month, he's bound to get attached. Charlie denies this until he crosses paths with the beautiful and mysterious Eva, played by singer/actress Cassie. They may agree to a casual affair, but eventually Charlie is questioning whether he may actually want more.

A Broadway artiste turns a faded film star's comeback vehicle into an artsy flop.

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.

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.

Providing the romantic comedy genre with a decidedly queer twist, THE ONE is an effortlessly charming tale which proves that love is never simple! Hunky Daniel couldn’t have it better: great parents, a successful career and his beautiful fiancée Jen. But in his seemingly perfect life, there is one temptation- he has a thing for his adorable, openly gay former college classmate Tommy. After a few drinks, Daniel succumbs to his repressed desires sending these two on a torrid affair. Funny how love and lust have a way of messing up even the best laid plans of man!

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

Christmas is approaching, and Paul's adopted sister Alana is coming home for the holidays. This won't be just a regular family celebration, as she's recently engaged and the weekend will be spent planning her June wedding with her best friends Roy and Vicki. Problem is that Roy is Paul's ex-boyfriend, and the two young men haven't seen each other since their very messy breakup. Nervous about seeing his ex again, Roy talks his good friend Gavin into joining him for the weekend, and pretending to be his new boyfriend. When Paul and Gavin meet, sparks of attraction fly, but Gavin thinks Roy's still hung up on Paul. This charming romantic comedy is a funny look at family bonds, misunderstandings and the "perfect wedding

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 story centered around a transitional point in the life of Ave Maria Mulligan, the heart of her community in the Appalachian Mountains of Virginia.

The romantic and coming-of-age misadventures of a 13-year-old American living in Germany.

A pair of high school rappers have two major goals - make music and get hot girls. The best way to get both is to throw the biggest and best house party ever! The night of the party, one of the boys is grounded by his parents, so it's up to his best friend to break him out of his house confinement and get the party started.

When brokenhearted Stan flies to Austin for the weekend in hopes of "accidentally" running into his ex-girlfriend Cathy, he arrives to find their best friends Jeff and Kara in the middle of their own vicious breakup. Before too long, battle lines are drawn – and with the Air Sex World Championships in town, anything can go down.

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?

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.

The modern-day story focuses on two beautiful young vampires who are living the good nightlife in New York until love enters the picture and each has to make a choice that will jeopardize their immortality.

Best pals Jason and Daniel indulge in casual flings and revel in their carefree, unattached lives. After learning that the marriage of their friend Mikey is over, they gladly welcome him back into their circle. The three young men make a pact to have fun and avoid commitment. However, when all three find themselves involved in serious relationships, they must keep their romances secret from one another.

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.