Live Your Pittsburgh Romantic Comedy

Yinz had me at hello

From Pittsburgh International Airport to Kennywood, Pittsburgh has been the site of some of the most memorable romantic comedies in film.

Ready to make fiction into reality? Turn your life into a Hallmark Channel movie and follow our feel-good guide to living your Pittsburgh romantic comedy.

The Strip District
Credit |
Jody Mader Photography

Find the Perfect Meet Cute Spots

The meet cute is one of the most important elements of the romcom when our two star-crossed lovers interact for the first time. Recreate your favorite meet cutes around Pittsburgh taking inspiration from local businesses and landmarks. You can go the "You've Got Mail" route and pop into The Big Idea Bookstore in Bloomfield (just don't try to put your partner out of business) or sing along to someone else's music between sets at Mr. Smalls a la "500 Days of Summer."

Or create your own meet cute! Maybe you'll reach for the same cut of salmon at Wholey's Fish Market and graze hands, or discover a fellow cinephile who loves the directors you do at Row House. The unexpectedness of the meet cute is what makes it so endearing, so get out there and explore.

Make Your Love Story Montage

As the couple falls deeper in love, things usually get sped up for the audience in the form of a montage of their dates and special moments. Go on a "Pretty Woman"-esque shopping spree. Our four distinct seasons make it easy to date through snow, summer and falling leaves like "13 Going on 30." Better yet, make your own montage like Jim in "The Office" and edit all of the photos and videos you've made in Pittsburgh together that tells your love story even better.

Going solo? You can channel the Pittsburgh-filmed "Flashdance" which contains one of the most iconic montages in cinema as Alex trains for her big audition to "Maniac." Feel free to bust out those moves at clubs throughout the South Side or Lawrenceville.

Go On Romantic Strolls

Siri, play "I Melt With You" by Modern English. Much like the beloved stroll in 80s classic "Valley Girl", Pittsburgh has tons of places to walk hand in hand. Take the Riverfront Trail Downtown past the giant fountain of Point State Park. Walk Grandview Avenue atop Mt. Washington at dusk as the city lights up at night. Follow the footsteps of Pittsburgh playwright August Wilson and see the places that inspired him in the Hill District. Grab a blanket and find somewhere cozy to lay in the grass at Frick Park.

With 90 unique neighborhoods, you can also simply pick one, head out and explore together. Who knows what attraction, restaurant or experience you might find there?

The Grand Romantic Gesture

When you know they are the one in a romcom, it's time to bust out the grand romantic gesture. Something so over-the-top but full of love that any problems of the past are forgotten and the couple ends up together forever.

The century old Kaufmann’s Clock Downtown is our vote for your Pittsburgh-centric grand romantic gesture, whether you're paying the school band to help you serenade a la "10 Things I Hate About You" or just want to kiss in the rain like "Breakfast at Tiffany's."

In a "Sleepless in Seattle" situation? Tell them to meet you at the top of the Mon Incline on Valentine's Day for the best view of the city before enjoying a fantastic dinner from restaurants with scenic overlooks.

Further Research | Love Stories Shot in Pittsburgh

Want to just curl up with a good romcom instead? Don't worry; we've compiled a list of some of our favorite of the genre, all shot in and around Pittsburgh, and where to watch them.

Me and Earl and the Dying Girl
A tale of young love and a budding filmmaker in impossible circumstances

She’s Out of My League (Starz)
A romance begins at the Pittsburgh International airport

Zack and Miri Make a Porno (Hulu)
Two roommates, one who works for the Pittsburgh Penguins, find a creative way to get out of debt and eventually get married

Happiest Season (Hulu)
An inclusive winter romcom set in Pittsburgh

Adventureland (Paramount+/Pluto)
Two young adults fall in love against the backdrop of Kennywood, Pittsburgh’s iconic amusement park

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Jared B.

Author

Jared B.

Enthusiastic Pittsburgher

Always in search of the next great craft beer and arcade. Can be found in the Supporters Section of Pittsburgh Riverhounds games and at whatever festival is happening in the city.

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