Best First Dates on Film

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The first date. An event that strikes fear into the hearts of everyone. For many, it can be daunting, intimidating and even frightening. It’s an event that could easily make or break a relationship, and needs to be planned just right. Luckily, we can easily take a note from our favourite movies for great first date experiences and inspiration.

The latest film that will no doubt inspire a whole generation of young lovers is Southside With You, a romantic comedy-drama that follows a young Barack Obama and Michelle Robinson as they spend an afternoon together in Chicago’s south side in the summer of 1989. What happened on that fateful day planted the seeds for one of the most powerful relationships in the world.

From spending a night with a stranger in a different city to serenading an acquaintance in a music shop to find a common interest, we’ve rounded up the best dates in films.

Southside With You (2016)

Inspired by accounts of the first couple’s first date, Richard Tanne’s romantic and intimate directorial debut Southside With You follows the story of the charming first-year law associate Barack Obama (Parker Sawyers), as he takes reluctant attorney Michelle Robinson (Tika Sumpter) on a daylong trip in and around Chicago’s South Side in 1989. The pair spend the day bonding over their personal and political aspirations – Michelle to empower women and Barack to hold a position of influence in Civil Rights. Although the pair have no inkling they will someday make history together, their date marks the first spark of romance between the future first couple, making this sweet and inspiring love story all the more poignant.

Like Crazy – 2011

Go karts and walks on the beach sound like a perfect date for this crazy-in-love couple, who would do anything to be together. Like Crazy tells the story of Anna (Felicity Jones), a British exchange student who falls in love with Jacob (Anton Yelchin), an American. Everything seems perfect for the couple, who plan their future together after university, but they’re pulled apart when Anna is denied re-entry into the United States after staying in the country longer than her student visa allows. As a result, they’re forced to move on with their lives, though they never forget about each other. But it’s the moments where they reunite after being an ocean apart that’s undeniably beautiful. The actors were free to improvise much of the dialogue, with director Drake Doremus compiling only a 50-page outline of what would happen.

Nick & Norah’s Infinite Playlist – 2008

The Big Apple really does never sleep in this adaptation of Rachel Cohn and David Levithan’s 2006 novel of the same name. Nick & Norah’s Infinite Playlist tells the story of teenagers Nick (Michael Cera) and Norah (Kat Dennings) who form a bond through their love of music. Their romance starts off as a rocky one, as they meet when Norah asks Nick to pretend to be her boyfriend for five minutes to show up a mean girl at a high-school party. What then transpires is a crusade through New York City at night as they try to find their favourite band’s secret show and look for Noah’s drunken best friend who’s gone missing. The film illustrates the craziness of young love and how one night can change everything.

Once – 2007

The entirety of John Carney’s Oscar-winning film follows two unnamed people as they bond through their love of music. They meet when the girl (Markéta Irglová) sees the guy (Glen Hansard) busk in the heart of Dublin. She’s immediately lured by his music, but is more delighted to learn that he repairs hoovers and insists that he fixes her broken hoover. She also tells him that she’s a musician, and their first proper musical encounter is when we fall in love with them. The song they perform, ‘Falling Slowly’ won the Oscar for best original song, and it’s pretty clear that this is the moment that they fell in love with each other too. They never admit it because for them, they find musical solace within each other as a way to escape from their broken lives.

The Notebook – 2004

The date that the lead characters Noah Calhoun (Ryan Gosling) and Allie Hamilton (Rachel McAdams) go on has gone down as one of the most memorable in rom-com history. The night ends on their first date with Noah and Allie nearly run over by a car when they spontaneously decide to lay on the road and dance in the street without music. The Notebook, adapted from Nicholas Sparks’ 1996 novel, follows the courtship of Noah and Allie, a young couple who fall in love in the 1940’s, despite being from different worlds. But their love for each other isn’t enough to hold their relationship together; they are soon torn apart because of their social differences. The film has gained a rabid cult following since its release, while Gosling and McAdams’ on-screen chemistry was praised.

Amélie – 2001

The BAFTA-award winning Amélie was an instant hit and became one of the most well known French films of all time. It stars Audrey Tautou as the titular Amélie Poulain, a shy waitress struggling with isolation, who finds bliss by devoting her life to the people around her. She resorts her own life to a fantastical world, and she dreams of love and beauty. But in doing so, Amélie begins to leave behind her own life and her own quest for love until she meets Nino Quincampoix (Mathieu Kassovitz), a quirky young man who Amélie gradually ends up falling in love with. This French classic is a feel-good charmer that showcases Tautou as a delightful heroine, and introduced her to a wider international audience.

10 Things I Hate About You – 1999

10 Things I Hate About You is perhaps mostly remembered either for Julia Stiles’ love poem, or Heath Ledger singing his heart out with ‘Can’t Take My Eyes Off Of You’. But the date that their characters, Kat and Patrick, go on is one of the most romantic scenes in the film. After she helps him sneak out of detention, they take a paddleboat out to an island, shoot paintballs at each other and have their first kiss in the hay. The film, which is loosely based on Shakespeare’s The Taming of the Shrew, follows new student Cameron James (Joseph Gordon-Levitt) who tries to date Bianca Stanford (Larisa Oleynik). In an attempt to get around her father’s strict rules on dating, he gets ‘bad boy’ Patrick (Ledger) to date her goody two-shoes sister Kat (Stiles). This was Ledger’s first American film, beating out Josh Hartnett and Ashton Kutcher for the role.

Before Sunrise – 1995

Before Sunrise is essentially a feature-length date that follows two strangers, Céline (Julie Delpy) and Jesse (Ethan Hawke), who meet on a train and gradually fall in love over the course of a long night in Vienna. They spend their limited time together walking around the idyllic city, believing that they will never see each other again. This allows them to open up to each other, revealing more about themselves than they normally would and the chemistry is made so much more powerful by what’s left unsaid. The lead actors were allowed to make changes to director Richard Linklater’s script, which he wrote in eleven days and is largely based on a personal experience. The film gained two sequels (which were both nominated for the best adapted screenplay Oscar) and the series was showered with critical acclaim for the simplicity of its straightforward premise.

Say Anything – 1989

John Cusack’s infamous boombox serenade is immediately the standout scene from Say Anything. Cameron Crowe’s pitch-perfect post-high school love story, which also stars Ione Skye, follows aspiring kickboxer Lloyd Dobler (Cusack) who falls for valedictorian Diane Court (Skye) at their high school graduation ceremony. As they begin to fall in love, their relationship hits a bump in the road when Diane’s father tells her to break up with Lloyd. That’s when Lloyd goes to her house at dawn with a boombox, blasting out the track ‘In Your Eyes’ by Peter Gabriel, a song Diane loves. Cusack holding the boombox high above his head is the defining moment of the film, and a proud and unapologetic symbol of young love that defines old-school movie romance.

Pretty In Pink – 1986

The Howard Deutch-directed rom-com is perhaps remembered for its soundtrack, but the romance of the film is probably what contributes to its status as a cult classic. The film stars Molly Ringwald as Andie Walsh, a working-class high school girl who finds herself torn between two different guys, Duckie (Jon Cryer) her friend who’s always had a crush on her and Blane (Andrew McCarthy), the rich boy who she immediately likes. The final scenes of the film are the most iconic ones. Andie ends up making an important decision at the high-school prom, though it was meant to swing in the other direction; even writer John Hughes was allegedly unhappy with the ending. Nevertheless, the film is remembered as being a cult classic that defied the barriers of class and social cliques.

Southside With You is in cinemas 30 September 2016.