Best movies like That Awkward Moment

By following ten simple rules, 20-somethings Vince and Cameron spice up their relationship by sleeping around. But when their straitlaced friends get engaged, their relationship gets turned upside down. To put the rules to the test, they will go on the road to the Hamptons to crash the biggest party of the year where love triangles collide and off-the-wall mayhem ensues.

Matt Sullivan's last big relationship ended in disaster and ever since his heart's been aching and his commitment's been lacking. Then came Lent, that time of year when everybody gives something up. That's when Matt decides to go where no man's gone before and make a vow: No sex. Whatsoever. For 40 straight days. At first he has everything under control. That is until the woman of his dreams, Erica, walks into his life.

Ally Darling is realizing she's a little lost in life. Her latest romance has just fizzled out, and she's just been fired from her marketing job. Then she reads an eye-opening magazine article that warns that 96 percent of women who've been with 20 or more lovers are unlikely to find a husband. Determined to turn her life around and prove the article wrong, Ally embarks on a mission to find the perfect mate from among her numerous ex-boyfriends.

A couple with a newborn baby face unexpected difficulties after they are forced to live next to a fraternity house.

Emma is a busy doctor who sets up a seemingly perfect arrangement when she offers her best friend Adam a relationship with one rule: No strings attached. But when a fling becomes a thing, can sex friends stay best friends?

Upon discovering her husband's infidelity, Sandy leaves the suburbs and moves into the city. There, she befriends Aram, a guy whose wife only married him so she could get a green card. Sandy hires Aram to be her nanny, and it isn't long until Aram and Sandy find out they get along wonderfully and start to date. But is their relationship real or is it, in fact, just a rebound for both of them?

While visiting his hometown during Christmas, a man comes face-to-face with his old high school crush whom he was best friends with – a woman whose rejection of him turned him into a ferocious womanizer.

A slacker and a career-driven woman accidentally conceive a child after a one-night stand. As they try to make the relationship work, they must navigate the challenges of parenthood and their differences in lifestyle and maturity.

A modern reimagining of the classic romantic comedy, this contemporary version closely follows new love for two couples as they journey from the bar to the bedroom and are eventually put to the test in the real world.

In Manhattan, the British limousine driver Alfie is surrounded by beautiful women, having one night stands with all of them and without any sort of commitment. His best friends are his colleague Marlon and his girl-friend Lonette. Alfie has a brief affair with Lonette, and the consequences force Alfie to reflect on his lifestyle.

Matthew Hollis is man on holiday in Rio with his best friend. Both men have teenage daughters with them. When Matthew falls for his best friend's amorous daughter named Jennifer, they embark on a secret, if slightly one-sided relationship. Jennifer's father is furious when he finds out about the 'older man' in his daughter's life, and sets out to hunt him down with the aid of Matthew!

Three couples travel to a secluded cabin in an attempt to revitalize their lives through bizarre games of sexual dysfunction....and all heck breaks loose!

Four friends search for love and happiness while working at a California sandwich shop.

It’s the battle of wills, as Andie (Kate Hudson) needs to prove she can dump a guy in 10 days, whereas Ben (Matthew McConaughey) needs to prove he can win a girl in 10 days. Now, the clock is ticking - and the wildly entertaining comedy smash is off and running in this irresistible tale of sex, lies and outrageous romantic fireworks!

Remember that really cute girl/guy who said they'd call – and didn't? Maybe they lost your number. Maybe they're in the hospital. Maybe they're awed by your looks, brains or success. Or maybe... They're just not that into you.

Though Rachel 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. Ramifications of the liaison threaten to destroy the women's lifelong friendship, while Ethan, Rachel's confidant, harbors a potentially explosive secret of his own.

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.

Kassie is a smart, fun-loving single woman who, despite her neurotic best friend Wally’s objections, decides it’s time to have a baby – even if it means doing it herself…with a little help from a charming sperm donor. But, unbeknownst to her, Kassie’s plans go awry because of a last-minute switch that isn’t discovered until seven years later… when Wally gets acquainted with Kassie’s cute – though slightly neurotic – son.

Olive, an average high school student, sees her below-the-radar existence turn around overnight once she decides to use the school's gossip grapevine to advance her social standing. Now her classmates are turning against her and the school board is becoming concerned, including her favorite teacher and the distracted guidance counselor. With the support of her hilariously idiosyncratic parents and a little help from a long-time crush, Olive attempts to take on her notorious new identity and crush the rumor mill once and for all.

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.

Popular high schoolers and best friends Shawn and Nick decide to ditch football camp for cheerleader camp. For the girls and for the glory.

Dylan and Jamie think it's going to be easy to add the simple act of sex to their friendship, despite what Hollywood romantic comedies would have them believe. They soon discover however that getting physical really does always lead to complications.

A New York writer on sex and love is finally getting married to her Mr. Big. But her three best girlfriends must console her after one of them inadvertently leads Mr. Big to jilt her.

Dating coach Alex 'Hitch' Hitchens mentors a bumbling client, Albert, who hopes to win the heart of the glamorous Allegra Cole. While Albert makes progress, Hitch faces his own romantic setbacks when proven techniques fail to work on Sara Melas, a tabloid reporter digging for dirt on Allegra Cole's love life. When Sara discovers Hitch's connection to Albert – now Allegra's boyfriend – it threatens to destroy both relationships.

Duffy, the big man on campus, is marrying Adriana, a debutante heiress to a global wine fortune, right after they both graduate from the same prestigious university. Unfortunately, the final frat party of his college career is the night before his wedding, and there are many obstacles in his way, including a soon to be father-in-law who is less than happy with his daughter's choice.

Joe and Lucy are roommates and best friends. Lucy, whose love life is embarrassingly dull, convinces Joe, who is infatuated with a neighbor he's never met, that if they don't have stable romances within a month, they must jump off the Brooklyn Bridge.

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.

After dying in a car crash, Bobby Fantana is forced to pay for his misdeeds by becoming someone's guardian angel. He reluctantly agrees to watch over awkward high schooler Lenny Barnes, teaching him how to be cool and confident. As Bobby teaches Lenny, the two form a close bond.

Ordinary single girl Amanda Pierce unexpectedly finds herself sharing an awesome Manhattan apartment with four sexy supermodels. Determined to bring Amanda into their world, the models give her the ultimate makeover. The plan works fabulously as Amanda connects with next door charmer Jim Winston. That is, until one night...

After a distastrous first date for caterer Holly and network sports director Messer, all they have is common is a dislike for each other and their love for their goddaughter Sophie. But when they suddenly become all Sophie has in this world, Holly and Messer must set their differences aside. Juggling careers and social calendars, they'll have to find common ground while living under the same roof.

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 Dustin's girlfriend, Alexis, breaks up with him, he employs his best buddy, Tank, to take her out on the worst rebound date imaginable in the hopes that it will send her running back into his arms. But when Tank begins to really fall for Alexis, he finds himself in an impossible position.

Jack and his buddy Ben check in at a posh Florida resort, planning to spend every hour in hot pursuit of gorgeous babes. But their plans hit a major detour when they try to bed the wife of a conniving jewel thief. They'll have to outsmart him, a nasty security guard and an obnoxious jock if they're ever going to get a moment alone with the girls of their dreams!

Ed and Alice are two months shy of getting married when she realizes that she wishes she'd had a more active love life while still single. Reluctantly, Ed agrees to have an open relationship in the months before their wedding, and initially this seems to improve their connection, particularly in the bedroom. However, as Ed and Alice get more involved in their own flings, the experiment goes awry.

The film follows the marital and dating lives of three men and three women who unknowingly form a tangled web of relationships. Interspersing "man on the street" interviews with scenes from the six characters' lives, the film weaves a humorous and biting commentary on the game of love -- easy to start, hard to finish.

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.

A gigolo must contend with the prospect that he has found true love.

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.

Two British Chinese gay men decides to re-examine their lives following a death of their friend. Mel sleeps around whilst rejecting the love of Todd and Ash decides to cross dress to find his knight in shining armour.

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.

Tired of the unsatisfying singles scene, Glenn answers a personal ad and meets Adam, a handsome Southern man seeking a long-term relationship. The two hit it off immediately, but their initial attraction is soon put to the test. Glenn's gay friends say he'd be happier playing the field again, but his straight pals encourage him to work at the budding relationship.

Two friends are about to learn that they are "Grownups."

Taylor is a man who has no problems with women. So confident is he that he accepts a challenge from his friends: he has to secure proposals of marriage from three women of their choice.

After a career-ending accident, former NFL recruit Ian Hunter is back on campus, and he's putting his extensive skills with women to work as one of the masterminds behind a successful and secretive dating service. But when Blake Olson requests the services of Wingmen, Inc., Ian may have landed his most hopeless client yet. As Blake begins the transformation from hot mess to smokin' hot, Ian realizes he's in danger of breaking his cardinal rule....

Myles and Brody are best friends with two very different ways of finding love. Displeased with their current love lives, they make a pact to be together if neither finds love in ten year’s time. Now two months shy of their deadline, both friends set off to do whatever it takes to avoid ending up as each other’s last resort.

Cooper is an actor who sees life as one big party, while Ed is in advertising and takes life too seriously. When Ed gets stressed over a deadline he has to meet, his brother Cooper works hard in trying to get his brother hooked up with a girl, thus a long weekend of stress and beautiful women, culminating in Ed meeting, and making love to, the woman of his dreams.

Spencer turns to his best friend who's planned an unorthodox "mantervention" filled with debauchery to convert him from hopeless romantic to forever player, and in the process they discover that being in love is not so bad after all.

When her inability to commit leads to a breakup with her girlfriend, opera-loving writer Allegra winds up in the bed of amiable professor Philip. He is so smitten with Allegra that he dumps his lover, Grace, and convinces Allegra to continue their affair. When Allegra meets Grace, sparks fly, and she begins a parallel romance, unaware that her new lover is the woman Philip left to be with her.

Long-term couple Simon and Jason, along with daddy-ish Cooper and his boy du jour, escape to a mountain cabin for a three-day weekend away from their hectic city lives. Looking to spice up this long-standing tradition, they add a special twist to this years retreat - each of them must invite one attractive single friend to their mountain getaway.

Corrine's holiday season gets an unexpected dose of romance when she meets the mysterious Harold, who is on a deadline from a higher power to help Corrine find her true love by Christmas Eve. As the clock ticks down to Harold's deadline, Corrine must decide if she will open up to Christmas love.