Dating may feel like a lifetime ago, but I definitely remember how awkward and exciting it was. Those first dates, in particular. The forced conversation and mixed signals — it’s nothing like what you usually see in the movies. The creativity, humor and general sappiness found in those first dates are enough to make me swoon whenever I put on a rom-com.
If you need a little inspiration to recreate that first date feeling or need something to lord over your significant other, here are 10 epic first dates from some of my favorite movies:
Autumn in New York (2000)
It’s hard to find a more picturesque setting for a first date than Central Park on a gorgeous fall day. So when Charlotte (Winona Ryder) and Will (Richard Gere) meet up there for a stroll, their date looks picture perfect. Add in the poetry recitation and her clever way of snagging his watch and you have a magical first date.
Notting Hill (1999)
Inviting a famous actress to a dinner party takes balls. But it’s the fact one of the guests doesn’t recognize her that makes this first date scene so entertaining. There’s no better way to test a relationship’s potential than to introduce your date to your friends and Anna (Julia Roberts) surely passed the test with William’s (Hugh Grant) crew.
50 First Dates (2004)
Breakfast dates are always a good idea (especially with waffles). Not as loaded as a dinner date. Unless, of course, your date has amnesia. This comedy starring Adam Sandler and Drew Barrymore is full of first dates, but it’s the actual first one — the honest one — that is the best of them all.
10 Things I Hate About You (1999)
Was their first official date real or not? That’s up for debate, given the whole paid seduction thing. But Patrick (Heath Ledger) and Kat’s (Julia Stiles) paintball outing seems like a fantastic way to avoid first-date weirdness — as long as your date knows what to wear in advance.
Roman Holiday (1953)
Who hasn’t daydreamed about riding around Rome on a Vespa with a handsome date? While not started with the best of intentions, Princess Ann (Audrey Hepburn) and reporter Joe’s (Gregory Peck) day spent exploring the city’s most famous attractions is still #dategoals. I’d skip falling into the river though.
Pitch Perfect (2012)
First dates don’t have to be fancy. Sometimes the best way to break the ice and win someone over is to just watch a classic movie, like The Breakfast Club. And that’s exactly how Jesse (Skylar Astin) and Beca (Anna Kendrick) spend their first adorable evening together. Just maybe make sure you have the place all to yourself first.
Serendipity (2001)
The opening of this romantic comedy is a quintessential meet-cute, which turns into a pretty epic first date. After a chance meeting at Bloomingdales, Sara (Kate Beckinsale) and Jonathan (John Cusack) spend the day enjoying dessert, ice skating, and looking for signs around NYC proving their destiny is to be together.
Before Sunrise (1995)
Love is all about taking chances, which is the message at the heart of this romantic comedy about two strangers who meet on a train from Budapest to Vienna. Jesse (Ethan Hawke) convinces Céline (Julie Delpy) to spend his last night in Europe with him, wandering the streets of the city, talking about everything under the sun.
Titanic (1997)
It’s as if they knew what was coming … deciding to buck their different social standings, Jack and Rose’s first date was all about living in the moment. After a somewhat uncomfortable dinner with her upper-class cohorts, they end up dancing the night away below decks and falling in love aboard the doomed ship.
Hitch (2005)
Dating guru Hitch’s (Eva Mendes) idea to take Sara (Eva Mendes) for a private tour of Ellis Island via jet ski from Manhattan was very cool. Aside from the part where he kicked her into the Hudson River. Even though it briefly went off the rails, this first date certainly beat the usual dinner and a movie itinerary.
Which first date do you wish you’d been invited on? Share your thoughts in the comments.
