Top 10 Captivating Movies Like 'How to Be Single'

Updated on October 24, 2019
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Rahul is a movie addict who can never get enough of good films. His all time favorites are Inception, 12 Angry Men, and Scarface.

What Movies Are Like How to Be Single?

Nobody likes feeling lonely. While couples are involved in their lovey-dovey antics, single men and women often take a bitter world view. Fortunately, they have an escape in the form of romantic comedy films. People can't get enough of this genre. Starring Dakota Johnson, Rebel Wilson, Alison Brie, and Leslie Mann, How To Be Single will certainly elevate your mood.

As the title suggests, this flick follows the shenanigans of four single women in New York City. Living wild and free is their motto, but they learn soon enough that it's not the key to happiness.

This film from Christian Ditter aptly shows that romantic relationships are an integral part of everyone's life. The best thing about this film, however, is that it doesn't glorify it. Sometimes finding yourself takes precedence over finding a soulmate.

If you enjoyed this flick and are looking for some movies like How to Be Single, we got you covered.

Movies Similar To How To Be Single

  1. My Big Fat Greek Wedding
  2. 10 Things I Hate About You
  3. Groundhog Day
  4. Juno
  5. Hitch
  6. 40 Year Old Virgin
  7. Chasing Amy
  8. There's Something About Mary
  9. Four Weddings And A Funeral
  10. 50 First Dates

1. My Big Fat Greek Wedding

For fans of the rom-com genre, this one's a cult classic. My Big Fat Greek Wedding's unique screenplay and a cavalcade of quirky characters make it a spellbinding experience.

The story follows the lives of Toula and Ian. Coming from an orthodox Greek ancestry, Toula's tires her best to ensure that her family accepts Ian as the groom.

Toula and Ian's incredible chemistry will more than satisfy those who are looking for that romantic spark. Those who aren't as romantic also have plenty to look forward to. The cultural differences between the Greek and the American way of life will leave you amused.

From the kooky antics of the uncles and aunts to sheer absurdness of the whole situation, this romantic comedy will leave you in splits. It's a gem of a film, no matter how you slice it.

2. 10 Things I Hate About You

This 1999 rom-com starring Heath Ledger and Julia Stiles is an instant classic. The film set the cash registers ringing the box office when it released and still enjoys a huge fan following. 10 Things I Hate About You neatly ties teen romance with humorous scenarios and plenty of sass.

Stiles plays Kat, a rebellious senior who has made quite a name for herself as an anti-social person. However, she has a sweet younger sister Bianca, who wants to date - something her father will never agree to unless Kat also starts seeing someone.

In comes Patrick, played by Heath, a high school bad boy who gets paid to get closer to Kat and take her out on dates. As you can guess, all hell breaks loose eventually when she learns about her false relationship. While the plot may be corny, Stiles and Ledger's stellar performances keep the show running.

It's equal parts silly and emotional, making it a perfect feel-good film for people of every age group. If you're looking for an outlandish movie like How to Be Single, 10 Things I Hate About You should be right up your alley.

3. Groundhog Day

Although it's generally lumped in the rom-com category with the others, Groundhog Day is anything but that. There's a supernatural element at the heart of this tale and a message so universally inspirational it'll definitely move you, even if you're a stone-hearted cynic.

Comedy king Bill Murray plays the pig-headed Phil Connors, a selfish, self-loathing local weatherman. He goes to a small town with his producer Rita, and here's where things get super weird. Phil wakes up every day only to find he is living the same day over and over again. Stuck in some weird curse or time loop, he must live this nightmare until he mends his ways.

Initially reluctant, he eventually learns his lesson and falls in love with Rita. Murray is unstoppable in this feature. His frustration, exasperation, and mean-spirited demeanor guarantee a few laughs. The ultimate message of how we never learn from our mistakes and keep repeating them, makes us introspect.

Groundhog Day should be watched over and over again until we learn our lessons, too. Trust me, it's that good.

4. Juno

Starring Ellen Page and Michael Cera, this 2007 indie film finds its charm as it delivers its story. Though Juno and Paulie, the main characters, are at the center of this movie, the story isn't just about them. Juno is only sixteen when she gets pregnant with Paulie's child. Confused about what to do with her life, she takes the help of friends and family to figure out if she should keep the baby.

The strength of the film lies in its comedy, for it conveys a lot through light and breezy demeanor of its characters. Talking about complicated real-world problems like teen pregnancy and complications that arise in relationships, Juno says a lot without making anything super-obvious.

5. Hitch

Hitch is sleek, cheeky, and slapsticky in certain places. This flick might not find its way in the romantic comedy hall of fame, but it's certainly up there. Will Smith plays Hitch, a suave, sophisticated dating coach, who's famous for teaching men different techniques on how to woo women. Working anonymously, for the most part, his life takes an interesting turn when he meets his new client, Albert.

Albert is chubby, nerdy, and wants to date the actress, Allegra Cole. Needless to say, his wild ambition presents a real challenge to the famous dating coach. Hitch tries his best to get cracking on this tough case, and hilarity ensues as most of his advice backfires. Brainstorming sessions with his new client aside, Hitch is also trying to get his love life in order as he dates a cynical columnist.

However, all hell breaks loose when his profession catches the public eye and he's demonized as a womanizer. With a plot this capricious, you can already imagine crazy scenarios Hitch and Albert have gotten into.

The chemistry between Will Smith and Kevin James is another revelation. Their initial awkward phase slowly turns into a bromance, adding another dimension of fun.

6. 40 Year Old Virgin

You must have heard of this film at the very least if not seen it already. In case you haven't witnessed the awesomeness of Steve Carrell on screen, now's the time to redeem yourself.

As the self-explanatory title suggests, Carrell plays a 40-year-old retail shop salesman, who's also, yes, you guessed it right, a virgin. After a super awkward and hilarious conversation, his co-workers deduce he has never gotten laid.

And thus begins the quest of trying to get this man some tail, which results in some ludicrous situations. There's also romance on the table as he falls for Katherine Keener's character in the film. Surprisingly, their love story is quite mature and no-nonsense for the most part, with a major focus on lewd jokes and slapstick humor.

Highlights include the toaster scene. You'll understand what I'm talking about when you watch the film.

7. Chasing Amy

Another classic from the archives, Chasing Amy's plot is a nightmare-come-true for those who are crushing on someone. Holden, played by Ben Affleck, wiles his days away as an amateur comic book artist. His life takes a major turn when he meets Alyssa, and the two hit it off instantly. However, there's one major problem; she's is a lesbian! A harrowing nightmare indeed!

In spite of knowing that there's no chance of anything romantic taking place between them, Holden befriends her and they grow close. But, unrequited feelings never stay hidden for long and when Holden spills it all, Alyssa is completely devastated. It doesn't take long before her hurt turns into fury.

Although the topic seems rather serious, it has been told light-heartedly. The thought-provoking concepts of sexual orientation have been beautifully embedded in between comic moments. The best part about the film, though, is that none of its life-lessons seem preachy. From the moment they meet till the very end, Chasing Amy feels real.

8. There's Something About Mary

Considered to be on the grosser side of the rom-com genre, this Ben Stiller and Cameron Diaz starrer is a cinematic gem. While the love story aspect takes the short, sweet route, funny set pieces truly make this film memorable.

Ben plays a man who hires a detective to spy on his high school crush, Mary. However, the investigator misleads Ben when he sees how stunning she looks. He reports back saying she's gotten fat and has four children with three different men, making Ben lose all interest.

As you can see, with multiple men vying to win her over, this film already has serious potential as a comedy film. When you witness how brilliantly it has been executed, it will leave you amazed, if you can spare a moment from laughing, that is.

Crazy, stupid and downright weird in some place. This flick holds back nothing when it comes to delivering its comedic punches. Watch this goofy masterpiece first and thank me later.

If you're looking for some movies like How to Be Single, There's Something About Mary should be your best bet.

9. Four Weddings And A Funeral

When a rom-com gets selected by the Academy for Best Picture, you know it's something special. Four Weddings And A Funeral enjoyed critical acclaim as well as love from the audience. Starring Hugh Grant in the lead, it follows his multiple encounters with a woman named Fiona, played by Kristen Scott Thomas. The duo keeps bumping into each other in four different weddings and finally, a funeral.

This 1994 flick puts more emphasis on the romance part than the comedy. Watching the British actor bumble on about love on has a certain fascinating quality to it. The film is cheesy in parts but it's well aware of that.

Watch it for the quality performances of the entire cast and you'll understand why the film made the cut for Best Picture alongside gems like The Shawshank Redemption, Pulp Fiction, and Forrest Gump.

10. 50 First Dates

Adam Sandler's films are generally not very tasteful. His brand of comedy doesn't have a lot of admirers. However, he can also be full of surprises, as he proved with this film. This Drew Barrymore starrer can be best described as cute, with its heart set in the right place.

Sandler plays Henry, a veterinarian who falls in love with a woman named Lucy during a Hawaiian vacation. But Lucy, played by Barrymore, suffers from short term memory loss. She's unable to remember anything from the day prior. Henry has his work cut out as he must make her fall for him every single day. With such astronomically bad odds, you can't help but feel bad for him and admire his love and devotion.

The plot, although unusual, keeps the film afloat. It's cheesy, sweet, and captivating, all thanks to strong performances from the lead actors and a heart-warming storyline. Don't miss out on this one.

That's about it, for now. Despite my best efforts, I know I might have missed out on some excellent movies like How To Be Single. If you have any suggestions, let me know in the comments section.

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