20 best movies like That Awkward Moment (2014)

A recent college graduate sets out to win back the girl of his dreams.

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.

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.

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.

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?

A small business owner is about to lose her shop to a major corporate development.

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.

Emma Corrigan, a girl with a few secrets on a turbulent plane ride, thinks she’s about to die, Emma spills them all to the handsome stranger sitting next to her. At least, she thought he was a stranger. But then, her company’s young and elusive CEO, arrives at the office. It’s him. And he knows every single humiliating detail about Emma.

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.

As her marriage dissolves, a Manhattan writer takes driving lessons from a Sikh instructor with marriage troubles of his own. In each other's company they find the courage to get back on the road and the strength to take the wheel.

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.

Two young people arrive in New York to spend a weekend; once they arrive they are met with bad weather and a series of adventures.

The comedy follows Jefferson, a ski-bum temp worker, whose singular joy comes from an annual excursion to the slopes with fellow slacker Curtis. But when Jefferson falls for Stephanie, an ambitious go-getter, he is forced to re-evaluate his priorities.

A small town waitress gets a nail accidentally lodged in her head causing unpredictable behavior that leads her to Washington, DC. Sparks fly when she meets a clueless young senator who takes up her cause - but what happens when love interferes with what you stand for?

Manhattanite Ashley is known to many as the luckiest woman around. After a chance encounter with a down-and-out young man, however, she realizes that she's swapped her fortune for his.

When a reporter encounters the eldest son of a famous political family at a mountain retreat, she winds up pretending to be his girlfriend over Christmas so he can save face with his family. Should she secretly expose newsworthy scoops about the famous family in order to save her job, or trust that she's falling in love for real? Stars Patricia Richardson and Katrina Law.

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

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.

New York City is full of lonely hearts seeking the right match, and what Alice, Robin, Lucy, Meg, Tom and David all have in common is the need to learn how to be single in a world filled with ever-evolving definitions of love.

After a man finally gets over his former girlfriend, who has moved to Los Angeles and become a television star, and falls in love with another woman, the former girlfriend's show is canceled and she wants him back.

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?

A young woman is forced to reflect on her first relationship when she inadvertently moves into her ex boyfriend's apartment building.

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).

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.

A young woman with Asperger's tries to find her first boyfriend with a little help from her older sister.

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.

Divorced and demoralised, Amy Minsky’s prospects look bleak when she is condemned to move back in with her parents at the age of 35. Everyone wants to help but, as her patience level with advice is plummeting, a bold teenage boy enters her life, igniting her last bit of self-esteem.

Forlorn heiress Penelope Wilhern is cursed, and the only way out is to fall in love with someone of suitable stock. But how can she find her soul mate when she's sequestered inside her family's estate with only her parents to keep her company. This untraditional fairy tale about a girl who bucks convention to create her own happy ending.

Carlos is a man who goes to a coffee shop-library to take a cup, where Irene is reading a book. Not a reason for it, Irene close to Carlos and talks with him, starting a friendship with a little rules: no pasts, no birth names, no modern ways to contact between them (as Internet or similar), and finally not falling in love each other. Calling themselves Hada Chalada ('Crazy Fairy') and Duende Chiflado ('Mad Goblin'), both pass the days walking around the city engaged with magic, surrealist and funnies conversations about life, love and themselves, at the same time that Carlos tries to end his new script with his friend Cristóbal, and eccentric writer obsessed with Japan.

Teenager Rick Stevens is willing to do whatever it takes to win the heart of Nina Pennington. He'll have to deal with his best friend's horny mom, a drug abusing boss and even the mob if he ever hopes to land the girl of his dreams. Love is never easy!

A sex therapist goes through puberty after the successful removal of a benign tumor resting against his pituitary gland. He experiences all the changes and effects of puberty over a three-week period.

With his family away for their annual summer holiday, Richard Sherman decides he has the opportunity to live a bachelor's life. The beautiful but ditzy blonde from the apartment above catches his eye and they soon start spending time together—maybe a little too much time!

When Anna Parisi, an unemployed fine arts painter, is unable to make ends meet, she is hired to become a personal Christmas shopper for Marc, an uptight corporate exec. As they begin working together, Marc learns that Christmas giving has less to do with the amount of money spent and more to do with the importance of the gift, while Anna discovers she might find success as an artist in a way she never expected. The best gift of all of course is the love they discover with one another.

Susanna gladly accepts help one day from handsome stranger Nate at her parents’ garden store in small-town Georgia. Sparks between them fly, but when a photo of them gets leaked to the press, Susanna is in for the shock of her life when Nate is called back home by his mother… For his coronation as the King Nathaniel of Cambria!

After a one night stand Deb wakes up in the middle of a zombie apocalypse.

Dan Farrell, a single father and firefighter unexpectedly falls for local florist Kate just two weeks before his stations’ annual Valentine’s Day fundraising ball. But Kate’s recent ex returns to town to win her back with a marriage proposal. Will Dan suit up to fight for love, or let the flame with Kate burn out?

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?

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

Romance novelist Liam Bradley (Dylan Bruce) has already found massive success with three books written under the pen name Gabriel August, but he's mysteriously unknown to his legions of readers. With his first book written as a way to heal after a broken relationship, Liam has slowly become disheartened with writing strictly for romantic fantasy, something evident to a sweet, but honest, journalist who reviews books, Sophie Atkinson (Amy Acker), whom he meets by chance on a plane. The two begin a tentative relationship in Sophie’s home town of Portland, Oregon, where Liam has come to find inspiration for his newest entry. Liam’s agent puts him on the spot with a long-planned reveal of Gabriel August’s true identity, but Sophie doesn’t know of his public persona. The longer Liam avoids telling her the truth, the deeper a hole he digs for himself. Will their romance survive once his true identity comes to light?

Rahul and Riana meet each other for the first time, get drunk, and awake the next morning to find that they have gotten legally married to each other.

The story of Charlie Darby, who has everything going for him: a great job, friends, family, the whole package. The one thing Charlie doesn't have is love, because every time he gets close, he goes clinically insane. When he meets the perfect girl, Charlie must overcome his psychosis to claim his chance at true love.

After a zombie becomes involved with the girlfriend of one of his victims, their romance sets in motion a sequence of events that might transform the entire lifeless world.

Tripp, an attractive man in his thirties, is still living with his parents Al and Sue. Tripp's best friends Demo and Ace are also still living in their parents' homes and seem proud of it. Al and Sue are not happy, however, and are fascinated when friends whose adult son has recently moved away from home reveal they hired an expert to arrange the matter and couldn't be happier with the result.

When a winter storm hits Cleveland and grounds flights, the nearby hotels quickly fill up with stranded travelers. Nina, a pilot, reluctantly agrees to let her arrogant but charming fellow pilot, Brady, stay at her nearby parents' home. But when they discover her family is hosting a tree trimming party that night and that her ex will be there, Brady pretends to be her boyfriend to help her out.

Jenny Farrell is getting married. But how will her straight-laced family react when they find out that the woman they thought was their daughter’s roommate is actually her fiancée? As the old-fashioned Farrells attempt to come to terms with the prospect of a surprise daughter-in-law, they face a difficult choice: either adapt with the times or risk being left behind.

A sudden loss disrupts Carol’s orderly life, propelling her into the dating world for the first time in 20 years. Finally living in the present tense, she finds herself swept up in not one, but two unexpected relationships that challenge her assumptions about what it means to grow old.

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.

Lifelong friends Kate (Mamrie Hart), Evie (Grace Helbig) and Charlie (Hannah Hart) are in a rut. Kate spends her days at a middling job and her nights alone or on failed dates. Evie is married with the in-laws from hell, wandering from one charitable cause to the next. Charlie has the girl of her dreams but just can’t seem to pull her business (or her act) together. On the eve of Kate’s 30th birthday, she agrees to let Evie and Charlie throw her a party. But what’s supposed to be a simple celebration becomes a wild who’s who of past and present, and things quickly spiral out of control.

Dave, a high school senior, spends most of his time pining away over a girl he can’t have. Aubrey, a junior with artistic aspirations, has a hot boyfriend who doesn’t quite understand her or seem to care. Although they go to different schools, Dave and Aubrey find themselves at the same party. When both head outside to get some air, they meet. A casual conversation sparks an instant connection, and, over the course of a weekend, things turn magical, romantic, complicated, and funny as Aubrey and Dave discover what it's like to fall in love for the first time.