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Romantic Comedy Movie Tournament: Round 2

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Feb 03, 2020 9:27 PM
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Constance Wu, Crazy Rich Asians
1/18
Warner Bros. Pictures

Crazy Rich Asians

Based on the popular book by the same name, Crazy Rich Asians follows Rachel Chu on her trip to Singapore to meet her boyfriend's family, only to find out that they are one of the richest families in the country.

As she is thrown into the spotlight, she must deal with trying to keep her sense of self while trying to fit in, and learning if this is even what she wants.


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2/18
Netflix

To All the Boys I've Loved Before

Imagine if your crush learned all your secret, deepest thoughts about them. Now, imagine if five of your crushes learned that!

In To All the Boys I've Loved Before, also based on a popular book, that's exactly what happens to Lara Jean after her younger sister mails out love letters Lara had written, but never mailed, to her crushes. Including one to her older sister's ex.

To avoid confronting him, Lara strikes up a fake relationship with Peter Kavinsky, another one of the letter recipients, but as their fake dating progresses, real feelings develop.


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3/18

Crazy, Stupid Love

Grab the tissues, because this heartwarming movie that interconnects so many love stories still hits us right in the feels.

After Cal Weaver (Steve Carell) learns his wife has cheated on him, he enlists playboy Jacob Palmer (Ryan Gosling) to help him become a hit with the ladies.

Meanwhile, Jacob's player tendencies are derailed when he meets Hannah (Emma Stone) and watching the two recreate the Dirty Dancing lift is still our favorite Stone/Gosling collaboration.


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4/18
Snap Stills/Shutterstock

When Harry Met Sally

The quintessential romantic comedy starring Meg Ryan and Billy Crystal is still one of our favorite stories about two friends who end up falling for one another.

We'll have what she's having.


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5/18
Paramount Pictures

How to Lose a Guy in 10 Days

Advice columnist Andie and marketing executive Ben are each trying to impress their respective bosses. Andie is working on a piece on how you can drive a man away while Ben is trying to prove he can make any woman fall in love with him.

The two start dating one another, unaware of the other's ulterior motives, but things get complicated when real feelings start to develop.


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6/18

Sleepless in Seattle

After Sam's son Jonah calls into a radio program wanting a new wife for his dad, hundreds of women fall for the architect, including engaged Annie Reed. 

Annie writers to Sam to meet her on the observation deck of the Empire State Building on Valentine's Day, and the rest is a happily ever after.


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7/18

You've Got Mail

Local bookstore owner Kathleen Kelly is at odds with corporate book chain owner Joe Fox, making them sworn enemies.

However, to neither of their knowledge, they have been writing to one another via an anonymous Internet romance, and when the moment of realization hits in this movie, the tears flow.


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8/18
Touchstone/Kobal/Shutterstock

Pretty Woman

Big mistake, huge!

You know this classic by now, where Vivian, a sex worker, and her client, Edward, start to fall for one another after spending time together in LA.

But despite our many re-watches, we still never fail to laugh and cry at one of the most defining movies in the genre.


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9/18
Moviestore/Shutterstock

The Wedding Singer

When a down-on-his-luck wedding singer (Adam Sandler) falls for Julia, there's just one problem: she's set to get married.

He must work against the clock to get her to fall for him before she walks down the aisle.


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10/18
Sony Pictures/Kobal/Shutterstock

The Holiday

Quick, book an Airbnb!

At least, that's what you'll want to do after watching the home-swapping romance The Holiday, where two women switch places for the holidays to get away from their respective situations only to find themselves in flirty, fun new ones.


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11/18
Touchtone

Sweet Home Alabama

You can't ride two horses with one ass!

In this Southern-charmed romcom, fashion designer Melanie (Reese Witherspoon) heads back to Alabama to get her estranged husband to finally sign their divorce papers so she can be free to marry her new fiancé.

However, the longer she is back home with her roots, the more she questions which life path is truly right for her.


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12/18
Suzanne Hanover/20th Century Fox/Kobal

Never Been Kissed

Josie Geller (Drew Barrymore) is sent undercover to her old high school to research teen culture, but hits a snag in her plan when she's triggered by her own bad memories from her time at school as well as when her brother infiltrates the cool kids clique.

Meanwhile, Josie also faces a moral dilemma when she falls hard for her English teacher.


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13/18
Columbia

13 Going on 30

All 13-year-old Jenna Rink wants to be is thirty and flirty and thriving, and she gets that wish thanks to a little magic dust.

Now a successful magazine editor in New York, Jenna starts to wonder if this is really the life she wanted after reconnecting with Matty, her childhood best friend who has always been in love with her.


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14/18
Jason Bell/Universal/Studio Canal/Miramax/Kobal

Bridget Jones' Diary

After deciding to take control of her life, Bridget Jones keeps a raunchy diary by her bedside tale that chronicles everything from sex to food to the men she can't pick between.


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15/18
Gold Circle Films

My Big Fat Greek Wedding

After Toula meets Ian, a handsome teacher, she has fallen in love, her family is relieved their perpetually single daughter has found a man.

That is, until they learn that he's not a little bit Greek.


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16/18
Touchstone Pictures

The Proposal

In this star-studded romcom, Margaret (Sandra Bullock) is facing deportation to Canada until she claims to be engaged to Andrew (Ryan Reynolds), her assistant who can't stand her.

We love a enemies become lovers tale, and this is one of the funniest out there.


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17/18
Touchstone Pictures

10 Things I Hate About You

Kat has zero interest in dating, but her older sister Bianca isn't okay with that since their house rules are that until Kat gets a date, no one in the house can.

So, she tries to set up her outcast sister with new student Patrick. And despite her best efforts, Kat finds herself falling for the handsome new arrival.


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18/18

Four Weddings and a Funeral

Charles and Carrie meet at a wedding and fall for each other, only for the latter to leave him for the States.

Their paths continue to cross—over, as you guessed it, four weddings and a funeral—leading them to wonder what could be if the timing was right.


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