How We Created a Cinematic Engagement Session at Best Intentions, IL for Sarah & Jack!

So, you just got engaged! CONGRATS!! The ring is on your finger, the reality is sinking in, and suddenly, you’re in the middle of one of the most exciting times of your life. But before you dive headfirst into wedding planning, let’s talk about something just as important, documenting this moment in a way that actually feels like YOU. Sarah and Jack weren’t about to settle for a cookie-cutter engagement session. No awkward prom poses. No forced, overly “Pinterest-y” moments. They wanted something cinematic, moody, effortlessly cool, something that felt like their love story, bottled up in a series of stills. So, that’s exactly what we created! We built an engagement session that was personal, stylish and packed with nostalgia. A little city grit, a little vintage beauty, and a whole lot of LOVE! If you’ve ever wanted to turn your engagement shoot into a movie moment, keep reading, because this one was straight out of a film! Come read more about their engagement session at best intentions!

Sarah & Jack’s Dream Engagement Session in Chicago

This shoot wasn’t about posing, it was about telling a story!

Sarah and Jack’s love is rooted in the city, in movement, and in the everyday moments that feel small but actually mean everything. So instead of picking a random “aesthetic” location, we started with places that were already a part of their world! And it was PERFECT!    

• An “L” stop they pass through every day: Because what’s more Chicago than a train platform, a little city noise, and that fleeting moment before the next adventure begins?
• A vibey neighborhood bar (Best Intentions, obviously): Moody lighting, retro decor, the kind of place that makes you want to order a cocktail and get lost in the conversation!
• A slow walk through Logan Square: Because some of the best moments happen when you’re just being together.

They also brought personal touches, a vintage film camera, some killer sunglasses, and outfits that felt cool but comfortable, because this wasn’t just a shoot. It was a moment in their story, and we made sure it felt like them!!

First Stop: The “L” Train

There’s something about a train platform that just feels cinematic. Maybe it’s the anticipation, maybe it’s the movement, or maybe it’s the fact that it’s such an everyday part of life in Chicago. Either way, this was the perfect place to start! Jack pulled Sarah in close as the train whizzed by, the wind catching her hair at just the right moment. She adjusted her sunglasses with that effortless “cool girl” energy, while he watched her like she was the only thing that mattered. The best part? It didn’t feel like a posed moment. It was just them, living in their city, sharing a moment that they probably had a hundred times before but this time, we captured it!

Next Up: A Drink During Their Engagement Session at Best Intentions!

If you’ve never been to Best Intentions, let me set the scene. It’s got the kind of effortlessly cool, retro bar aesthetic that feels like it belongs in an old film. Dim lighting, vintage decor, and the kind of ambiance that makes you want to sip an old-fashioned and stay a while. Sarah and Jack fit right in. Here we capture amazing photos and memories that they will cherish FOREVER!

Final Stop: A Walk Through Logan Square

We wrapped things up with a slow stroll through Logan Square, one of Sarah and Jack’s favorite neighborhoods. This is where they go for coffee, for date nights, for Sunday morning walks. So, it only made sense to let them move through the city naturally, the way they always do, right? They held hands, twirled on the sidewalk, and leaned into each other at stoplights. The little moments in between were the ones that made the best photos!

Ready For Your Dream Engagement Session at Best Intentions Or Wherever Fancies You? Let’s Chat!

Wren And Rose Photography | Chicago Engagement Photographer

Here’s the thing, engagement photos should feel like you. Sarah and Jack didn’t want an over-the-top production, so we focused on the places they love, the details that matter, and the kind of moments they actually share in real life. The result? A session that felt cinematic but never staged. Stylish, but never forced. Personal, but still effortlessly COOL. Ready for me to capture yours next? Head to my contact page so we can chat about the ideas you have! If you want to learn more about me and what I do, click here. Can’t wait to hear from you!