Top 5 Romantic New York Movie Scenes You Can Recreate

Valentine’s Day is the perfect time for romantic New Yorkers (and visitors!) to plan the perfect date night.

Here in the Big Apple, of course, we have an advantage. Hollywood has spent years teaching us how to make the most of this enchanting city. Every street corner is the perfect stage for a one-act play, and every cafe is brimming with potential romance.

For those of you who have a special Valentine, here’s some inspiration for a day to make them swoon. Reenact one of these five romantic New York movie scenes this Feb. 14 for the ultimate day of love. Some of them are even near our popular New York tours if you want to extend your special day.

Read on for tips, inspiration, and movie clips to recreate your rom-com fantasy with your sweetheart in beautiful New York City.

1. A romantic New York meeting

How better to meet up with your sweetheart than in one of the city’s many parks? Riverside Park, in upper Manhattan, is where Meg Ryan and Tom Hanks shared one of their most romantic moments — as their real selves and not Shopgirl and NY152 — in “You’ve Got Mail.” 

The two met up at the 91st Street Garden in the 1998 film, and though the weather may be brisk for Valentine’s Day, we think it’s still worth a romantic visit, in the spirit of Kathleen Kelly and Joe Fox!   

One of the New York-based film’s other classic locations, Cafe Lalo, where the two have their first encounter, was once a popular spot for film buffs to come for a first date. However, the iconic NYC landmark closed at the end of 2024, leaving movie fans to find other spots to live out their rom-com fantasies. 

2. Leave it up to fate

No other city on Earth can match NYC for chance encounters. In “Serendipity,” sparks fly between Kate Beckinsale and John Cusack over a pair of black cashmere gloves, but fate has other plans for these two. 

They’ll separate and meet again, but not before partaking in a famed, romantic New York dessert at the film’s namesake restaurant, Serendipity 3. 

Book early to bring your date to this iconic Big Apple sweet spot. There are two locations: Upper East Side and Times Square, but true movie fans already know that the UES spot is the way to go. Of course, you should try one of the famous Frrrozen Hot Chocolates. There are several varieties, but the classic is always a good choice — get two straws to share! 

If your tastes run a bit more refined, you might order New York’s most expensive dessert. In the Guinness World Records section of the menu, you’ll find the Golden Opulence Sundae, which costs $1,000. It once held the record for the world’s most expensive dessert, before Serendipity 3 beat itself by creating an even MORE expensive dessert (not currently on the menu) that costs $25,000. If you want the Golden Opulence Sundae, you have to order ahead.

3. (More than) just friends

Maybe not the most romantic moment, but certainly the most well-known, the Katz’s Deli scene from “When Harry Met Sally” put this NYC institution on the world stage. You too can have what she’s having when you sit in their famous booth, marked with a sign hanging from the ceiling. Even if you don’t get to sit in that specific booth, you should definitely take a photo of the sign while you’re in the restaurant!

Katz’s Deli, which is located on 205 E. Houston St., caters to the late-night weekend crowds, which means you can go any time you like on Valentine’s Day. This spot is open from 8 a.m. to 11 p.m. during the week but open 24 hours on weekends, so if you want a hearty sandwich with your sweetheart late at night on Valentine’s Day after watching “When Harry Met Sally,” then so be it.

Don’t skip the pastrami — it’s Katz’s specialty — and make sure to have a few pickles. But for your own sake, don’t lose your ticket! If you know, you know. And if you don’t, it’s time to watch the movie again!

4. Reunite on top of the world

It’s a cliché, but there’s a good reason romantic New York couples have reunited at the Empire State Building again and again over the years. The observation deck is well known from the final moment of “Sleepless in Seattle.” This is the second Tom Hanks and Meg Ryan scene on this list, but it plays out a little differently. No one understands the romance of New York City quite like director Nora Ephron.

The Empire State Building is no stranger to romance. This unique spot is open until 10 p.m. on Valentine’s Day, so maybe make it your last stop of the evening. Of course, if you want to include this gorgeous building in your sentimental backdrop, we recommend meeting atop Rockefeller Center for the perfect skyline view. (Our Rockefeller Center Walking Tour includes a tour of this Art Deco city within a city, a romantic spot in its own right, as well as your ticket to the Top of the Rock where you can see the Empire State Building towering above its fellow skyscrapers.)

Once atop the Empire State Building — which is located on 34th Street between Fifth and Sixth Avenues — you’ll have 360-degree views. On a clear day or night, you’ll be able to see for miles over into New Jersey, far into Brooklyn, down to Lower Manhattan, into the Bronx, and beyond. The Empire State Building observatory is a must when you visit New York, whether you’re traveling with your sweetie, solo, or as a group. It’s why it’s the grand finale of our Midtown NYC Walking Tour.

Discover the magic of NYC’s iconic skyline up-close

Race to the Sky: Midtown NYC Walking Tour With Empire State Building

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But truly nothing says “I love you” like a warm embrace with your loved one while gazing out over one of the most beautiful cities in the world with nothing but the twinkling lights of the city around you. (And, well, other visitors, because this is the city that never sleeps!)

5. Have a broken heart? Have it in NYC

When love ends, the awkward encounters that follow are best staged in grand ol’ New York. One of these classic bittersweet moments can be found between Barbra Streisand and Robert Redford in Sydney Pollack’s “The Way We Were.” Reunited years after their separation, the two share a moment outside the Plaza Hotel, reminiscing, obviously, about the way they were.

Tour the iconic space outside the Plaza Hotel, hopefully under better circumstances. If you want to escape the chilly New York weather, though, I recommend you actually head inside the Plaza Hotel for your romantic plans. 

If you don’t want to actually plan an overnight stay at the famed hotel, you can at least dine at The Champagne Bar or The Palm Court. Both are open all day and would make for a lovely date spot. The Palm Court is especially known for its tea service if you’re looking for a fancy afternoon outing. 

Bonus: Cheer on the home team

The romantic season perfectly coincides with basketball season, and you can take in a Knicks game at Madison Square Garden just like Andie Anderson and Ben Barry, played by Kate Hudson and Matthew McConaughey in “How to Lose a Guy in 10 Days.” 

The game may not have been the most romantic in the film — that took place on a bridge, where we definitely won’t send you in the middle of winter on foot! — but it’s certainly one of the most fun places to visit from the movie.

Madison Square Garden is the World’s Most Famous Arena for a reason, so even if you can’t score Knicks tickets during your trip to New York, you’re sure to find some event happening, whether it’s a concert or hockey game. It’s also a very central location in the city, right near Herald Square and Penn Station, so it’s easy to access and easy to get to after you’ve visited other spots during the day.

Make the most of your next visit

Whether your next trip to New York is in time for Valentine’s Day or you just want a romantic visit with your loved one, the city has everything you need to make it special. Grab some of the city’s most iconic foods and sightsee at all of the must-see spots.

No matter how many times you come to New York, there’s always plenty to do and see, so don’t worry if you can’t get to everything on your list — that just means you have to come back again!