Meg Ryan fans read on… this engagement was built around visiting locations from You’ve Got Mail and When Harry Met Sally.

When Nina reached out to me months ago to help plan and capture their proposal to Emily while the two visited New York, I was so excited. Letting locations from You’ve Got Mail like the 91st Street Garden along with When Harry Met Sally gems like Katz’s Delicatessen and Sally’s upper west side brownstone be the foundation of our plan, we set out on a lovely afternoon around Manhattan.

The proposal

When I’ve captured proposals in the past, the couples have always arrived together while I wait. But if you’ve seen You’ve Got Mail, Tom Hanks & Meg Ryan’s characters agree to meet in person for the first time at the 91st Street Garden at the end of the movie (sorry, spoilers). So in true rom-com spirit, Nina came to meet me first and chat out our plan while Emily got ready and walked over to meet up for the big surprise. I loved this idea!

A lovely walk around the Upper West Side

As the rain stopped, we set out on a walk to Sally’s brownstone from When Harry Met Sally. When my couples are looking for a session that really feels like a day in NYC, I always recommend walking around a bit. Running across the street, yellow cabs zipping by, stopping in front of cool buildings – these little things really make an NYC gallery come together.

Photos on the subway, of course

Another city classic: the subway. It can be grimy and packed with people, but if you have spots you want to hit all over the city like Nina and Emily did, it just makes sense to hop on the train to get there. Plus, the photos can be so cute! To get from the upper west side down to the Strand for some When Harry Met Sally-esque bookstore shots, we hopped on the train.

At Katz’s… “hope you have what she had!“

One last stop: Katz’s Delicatessen. Harry and Sally sat inside and, well, you know the rest. But we just stopped for one quick shot out front to round off their session with some city light vibes.

New York City engagement photos on film

While I primarily shoot digital, I always bring along a roll or two of 35mm film for the vibes, because there’s nothing like capturing the city on film. I snagged some Portra 400 for this session (if you know, you know) and it was the perfect splash of nostalgia to add to their gallery, especially for this 90s throwback theme.

If you’re looking for a photographer to help plan your proposal or engagement in the city, I’d love to chat!