Romantic Pizza Date Night Photo Session on the Upper West Side

If you told me there is a food sexier than pizza, I'd show you these photos and argue-- there's not.

There are things you need to know about Gabriel and Matt. They have been dating a handful of months, but I think they are some of the funnest daters I know. Just the other day Gabriel sent me a photo of her and Matt wearing bucket hats while fishing in Central Park. They like to take people on food tours in NYC, like best dumplings and baked goods. Since they like food so much, I knew they would probably love a pizza date night. They are fun to be around as a couple (I feel like that's just an extra bonus) and the way they treat one another with kindness, silliness, respect, and dignity. It's the stuff of dreams. When they started dating and I met Matt, all I could think was-- wow, I'm so glad they found one another because they are such a great match. I didn't know modern dating could be as fun as they make it.

These two just know how to care for one another, and it really translates in their photos. These photos are a product of almost 100% candid interactions for the first thirty minutes and directed/prompted interactions the second half of their session. I love the pizza date idea because it gives you space to enjoy time together, but also gives us space to marry both candid and posed moments.

Couple enjoying pizza at Upside Pizza during a romantic NYC date night

Cinematic couple portrait outside Tom’s Diner in Morningside Heights

Late-night editorial-style couple photoshoot on the Upper West Side

Authentic candid moment between couple during NYC pizza date

Romantic couple sharing a slice at Upside Pizza, NYC

Couple sharing a slice at Upside Pizza on the Upper West Side

Nighttime pizza date in NYC with moody romantic lighting

Editorial-style portrait of couple toasting pizza slices at Upside Pizza

Romantic couple’s photo session inside NYC pizza shop

Morningside Heights couple laughing during pizza date

Moody film-style photo of couple eating late-night pizza in NYC

Couple captured through window of NYC pizza shop during date night

Authentic candid photo of couple on romantic pizza date in Manhattan

Silly couples moment captured at pizza counter in NYC

Neon-lit pizza shop couples session on the Upper West Side

Urban date night photoshoot in Morningside Heights

Gabriel and Matt laughing together during late-night NYC shoot

Couple playing with Instax camera during NYC date night session

Close-up of couple holding pizza slices at Upside Pizza

Here's how we could copy and paste the bare bones of their photo session to any couple's session.

1. Creating an intentional list to keep you engaged. They created a list of topics, silly date games, and embarrassing stories they wanted to save for this date. I've included the list they sent me so you can get idea-- they had a lot they wanted to cover. A lot that had them interacting with one another. Having this list gave them autonomy to enjoy one another without me interfering.

2. Loving on each other is key. They knew the assignment was to love on each other. If you're not a super physical couple, I always like to challenge my couples to appreciate things about their partner maybe they haven't attended to lately. Enjoy and touch those freckles on their cheek. Give their shoulder a kiss because you forget to most days. Give their bum a little squeeze every now and then because it's squish needs some squishing. If you think you might struggle to love on each other, I dare you to never stop touching body parts the entire time. See if you can meet the challenge.

3. Dress up a date night and expect the photos to be feel nostalgic and documentary meets lifestyle/editorial. We didn't make these as editorial as we could have, but I love how their relationship translates.

Through-the-glass portrait of couple enjoying a late-night meal

Romantic cinematic couple photography at Tom’s Diner NYC

Couple standing under neon lights outside Tom’s Diner after pizza date

Black and white romantic portrait from NYC pizza shop session

Flash photo of couple embracing in corner booth at Upside Pizza

photos that feel like riverdale

checkered floor pizza shop date photos

silly date lifestyle photo session

photos that feel like a movie taken by NYC photographer, Stine Creative

NYC couple walking hand in hand after romantic pizza night on UWS

Upper West Side couples photographer

Walking the crosswalk outside of Tom's Diner

Romantic Tom's Diner Photo Session

romantic couples city photo session in New York City

As an artist and photographer, I loved photographing this Romantic Pizza Date Night Photo Session on the Upper West Side. My goal was to make most of it candidly feel like a movie, giving direction only when necessary. Gabriel and Matt’s late‑night slice at Upside Pizza in Morningside Heights was pure cinematic magic. Practically, we timed their session for around 10:00 PM—just past dinner rush—so the shop would feel intimate and film‑noir cool. And it really was! The plus of having a couple's session at a pizza shop in NYC, is that most pizza shops stay open pretty late! This Upside location in Morningside Heights is also absolutely perfect for photos because of it's big glass windows. And you know we hit up the Softside soft serve while we were there too. I loved watching them dance around with their ice cream cones.

Matt and Gabriel treated it like any cozy date: they walked in, ordered their favorite pies, clinked slices for a “cheers,” and dove right in—while I took photos through the window to keep it feeling candid. I handed them an Instax before they went in and told them to snap silly Polaroid faces of each other.

Technically, I added FX prism filters—yes, the same kind real film crews use—to deepen that moody, movie‑like glow. Then we crossed the street to Tom’s Diner (the “every Seinfeld episode you’ve never seen” spot) where the neon sign’s pink and teal hues gave us an epic backdrop for more romantic night‑life portraits.

Do you love these Romantic Pizza Date Night Photo Session on the Upper West Side shots? Ready to plan your own cinematic date‑night or solo session in NYC? Let's start talking about what cinematic photo session would fit you best!