Best movies like That Awkward Moment

Similar in 87%

Mike and Dave Need Wedding Dates (2016)

Plot Summary:

Mike and Dave are young, adventurous, fun-loving brothers who tend to get out of control at family gatherings. When their sister Jeanie reveals her Hawaiian wedding plans, the rest of the Stangles insist that the brothers bring respectable dates. After placing an ad on Craigslist, the siblings decide to pick Tatiana and Alice, two charming and seemingly normal women. Once they arrive on the island, however, Mike and Dave realize that their companions are ready to get wild and party.

Similar in 89%

You, Me and Dupree (2006)

Plot Summary:

After standing in as best man for his longtime friend Carl Petersen, Randy Dupree loses his job, becomes a barfly and attaches himself to the newlywed couple almost permanently -- as their houseguest. But the longer Dupree camps out on their couch, the closer he gets to Carl's bride, Molly, leaving the frustrated groom wondering when his pal will be moving out.

Similar in 79%

Set It Up (2018)

Plot Summary:

Two overworked assistants with nasty bosses try to get their supervisors out of their hair.

Similar in 78%

How I Met Your Mother (2005)

Plot Summary:

How I Met Your Mother is an American sitcom that originally aired on CBS from September 19, 2005, to March 31, 2014. The series follows the main character, Ted Mosby, and his group of friends in Manhattan. As a framing device, Ted, in the year 2030, recounts to his son and daughter the events that led to his meeting their mother.

Similar in 77%

Knocked Up (2007)

Plot Summary:

For fun loving party animal Ben Stone, the last thing he ever expected was for his one night stand to show up on his doorstep eight weeks later to tell him she's pregnant.

Similar in 78%

Can You Keep a Secret? (2019)

Plot Summary:

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.

Similar in 75%

Two Night Stand (2014)

Plot Summary:

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.

Similar in 80%

Playing It Cool (2014)

Plot Summary:

The story of a young man disillusioned by love who meets a breathtaking young woman at a charity dinner by pretending to be a philanthropist. Turns out that she’s engaged to a guy who doesn’t like her going on dates. Challenged by the chase, and egged on by his eclectic friends, he feigns a platonic relationship in order to keep seeing her as he tries to conquer her heart.

Similar in 90%

About Last Night (2014)

Plot Summary:

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.

Similar in 80%

Neighbors (2014)

Plot Summary:

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

Similar in 79%

The 40-Year-Old Virgin (2005)

Plot Summary:

Andy Stitzer has a pleasant life with a nice apartment and a job stamping invoices at an electronics store. But at age 40, there's one thing Andy hasn't done, and it's really bothering his sex-obsessed male co-workers: Andy is still a virgin. Determined to help Andy get laid, the guys make it their mission to de-virginize him. But it all seems hopeless until Andy meets small business owner Trish, a single mom.

Similar in 89%

The Rebound (2009)

Plot Summary:

Sandy, upon discovering her husband's infidelity while watching her son's birthday video, leaves the suburbs and moves into the city. She gets an apartment that's above a coffee house where she befriends one of the workers, Aram, a guy whose wife only married him so she could get a green card. Aram's family thinks he's wasting his life and education by working in the coffee house. Soon after moving into the apartment, Sandy hires Aram to be her nanny while she takes on work for the first time since her children where born. It isn't long when Aram and Sandy find they get along wonderfully and start to date. But the question is: is their relationship real or is it, in fact, just a rebound for both of them?.

Similar in 77%

I Love You, Beth Cooper (2009)

Plot Summary:

A valedictorian's declaration of love for a high-school cheerleader launches a night of revelry, reflection and romance for a group of graduating seniors.

Similar in 78%

No Strings Attached (2011)

Plot Summary:

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?.

Similar in 87%

The Other Woman (2014)

Plot Summary:

After discovering her boyfriend is married, Carly soon meets the wife he's been cheating on. And when yet another affair is discovered, all three women team up to plot mutual revenge on the three-timing SOB.

Similar in 76%

Sleeping with Other People (2015)

Plot Summary:

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.

Similar in 84%

He's Just Not That Into You (2009)

Plot Summary:

Remember that really cute guy who said he'd call – and didn't? Maybe he lost your number. Maybe he's in the hospital. Maybe he's awed by your beauty, brains or success. Or maybe... he's just not that into you.

Similar in 78%

How to Be Single (2016)

Plot Summary:

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.

Similar in 89%

Valentine's Day (2010)

Plot Summary:

More than a dozen Angelenos navigate Valentine's Day from early morning until midnight. Three couples awake together, but each relationship will sputter; are any worth saving? A grade-school boy wants flowers for his first true love; two high school seniors plan first-time sex at noon; a TV sports reporter gets the assignment to find romance in LA; a star quarterback contemplates his future; two strangers meet on a plane; grandparents, together for years, face a crisis; and, an "I Hate Valentine's Day" dinner beckons the lonely and the lied to. Can Cupid finish his work by midnight?.

Similar in 79%

Just Friends (2005)

Plot Summary:

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.

Similar in 88%

What's Your Number? (2011)

Plot Summary:

Ally Darling (Anna Faris) 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.

Similar in 82%

Chalet Girl (2011)

Plot Summary:

While working a job at an exclusive ski resort to support her Dad, Kim learns to snowboard and is so good at it that she enters a competition with a huge cash prize. She has to dig deep to overcome her fears, but her life gets more complicated through her spoken-for boss, Jonny.

Similar in 76%

Leap Year (2010)

Plot Summary:

When yet another anniversary passes without a marriage proposal from her boyfriend, Anna decides to take action. Aware of a Celtic tradition that allows women to pop the question on Feb. 29, she plans to follow her lover to Dublin and ask him to marry her. Fate has other plans, however, and Anna winds up on the other side of the Emerald Isle with handsome, but surly, Declan -- an Irishman who may just lead Anna down the road to true love.

Similar in 75%

What Happens in Vegas (2008)

Plot Summary:

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.

Similar in 77%

She's Out of My League (2010)

Plot Summary:

When he starts dating drop-dead gorgeous Molly, insecure airport security agent Kirk can't believe it. As his friends and family share their doubts about the relationship lasting, Kirk does everything he can to avoid losing Molly forever.

Similar in 83%

Failure to Launch (2006)

Plot Summary:

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.

Similar in 90%

Friends with Benefits (2011)

Plot Summary:

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.

Similar in 79%

How to Lose a Guy in 10 Days (2003)

Plot Summary:

An advice columnist, Andie Anderson (Kate Hudson), tries pushing the boundaries of what she can write about in her new piece about how to get a man to leave you in 10 days. Her editor, Lana (Bebe Neuwirth), loves it, and Andie goes off to find a man she can use for the experiment. Enter executive Ben Berry (Matthew McConaughey), who is so confident in his romantic prowess that he thinks he can make any woman fall in love with him in 10 days. When Andie and Ben meet, their plans backfire.

Similar in 90%

Love, Rosie (2014)

Plot Summary:

Since the moment they met at age 5, Rosie and Alex have been best friends, facing the highs and lows of growing up side by side. A fleeting shared moment, one missed opportunity, and the decisions that follow send their lives in completely different directions. As each navigates the complexities of life, love, and everything in between, they always find their way back to each other - but is it just friendship, or something more? Based on Cecelia Ahern's bestselling novel, LOVE, ROSIE is a heart-warming, modern comedy-of-errors posing the ultimate question: do we really only get one shot at true love?.

Similar in 82%

Hitch (2005)

Plot Summary:

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.