I’ve known JD and Josh for years. We all worked together at an automotive tech startup in the Chicago suburbs — still do, actually — Josh has since gone off to do bigger and better things. So when they asked me to photograph their engagement session ahead of their destination wedding, it was an easy yes. Photographing people you actually know is one of my favorite parts of this job, and these two are some of my favorite people to spend a few hours with.
This post is part engagement session, part the absolute best proposal story I’ve heard in a long time, and part love letter to two specific Chicago spots if you’re a couple looking to do something similar.
How They Got Here
JD and Josh have been together a little over seven years. They met at work — same team for a stretch — and JD has gone on the record saying she barely gave Josh the time of day in those early days unless she needed him to code something for one of their projects.
Then came the company Christmas party. Apparently Josh’s interest finally became impossible to ignore, and with some match-making sorcery from their mutual friend Amy, they exchanged numbers. Coffee date a week later. The rest, as they say, is history.
Their relationship since has been built on the things that make a really good partnership work: cooking together, going to shows (live music, comedy, Broadway — anything), staying home with their dogs Tonks and Lupin, and, more than anything else, traveling. Their first trip together was Austin. Since then they’ve made it through several cities and a handful of countries. So a destination wedding isn’t a stretch — it’s exactly who they are.
The Proposal (Buckle Up)
Okay. I have to tell you about the proposal, because Josh played a very long game.
JD loves Harry Potter. Has loved it for years. And early in their relationship, Josh started this quiet little tradition of hiding small Harry Potter Funko Pop figurines around their place for her to find — just little surprises, always perfectly timed, always thoughtful. It became a thing.
Fast forward to them moving into a new home together. JD decorated her office with bookshelves and packed them with books and figurines. At some point, Josh quietly added a few new characters to the shelves. He also slipped in a special edition Harry Potter book.
And then he waited.
For three months.
For three months JD did not notice. Walked past the shelves daily. Nothing. Josh just kept on living his life, ring hidden in plain sight, waiting for her to spot it.
Finally, one evening while she was tidying up, JD clocked the new characters and got confused. When did I buy these? Wait — did I really only buy one book from the whole series? Why is this random one here? She pulled the book down off the shelf, opened it, and found a hollowed-out section right in the “Unbreakable Vow” chapter.
The ring was inside.
Sobbing, she walked into Josh’s office, where he was — and this is the part that kills me — in the middle of a game of Apex Legends. She held up the book and asked, “is this what I think it is?”
Josh dropped his controller, shouted into his mic “sorry boys gotta go — I just got engaged!” (his teammates were apparently as surprised as she was), gathered the dogs, and asked her to spend the rest of forever with him.
I cannot improve on that story. I’m not going to try.
The Session
For their engagement session, JD and Josh picked the two locations themselves, and honestly the pairing tells you everything you need to know about them as a couple: Lincoln Park Conservatory because JD is a serious plant mom and wanted to be somewhere lush and beautiful, and Off Color Brewing because they genuinely love their beer.
Plants and beer. Calm and casual. Exactly them.
We met up on a soft April afternoon. Josh wore plaid and jeans (peak Josh). JD wore a black leather jacket, jeans, and combat boots (peak JD). No formal styling, no wardrobe stress — just two people who already know what they like wearing what makes them feel like themselves. Which is, in my opinion, the entire point of an engagement session.
Lincoln Park Conservatory
If you’ve never been, Lincoln Park Conservatory is one of the best free things in Chicago. It’s a historic glass conservatory in Lincoln Park with several rooms — palm house, fern room, orchid house, show house — each one its own little world of light and green. For photos, it’s almost cheating. Even on a gloomy Chicago day, the light through the glass roof is soft and even, and the backdrops are endless.
We wandered through slowly. JD identified plants. Josh teased her gently about how many plants they have at home already. We stopped for portraits whenever the light caught something good.
Quick practical notes if you’re planning your own conservatory session:
The conservatory is free, but it requires advance reservations to enter, and any professional photography also requires a permit from the Chicago Park District. (I’m planning a separate post walking through the reservation and permit process for both photographers and couples — keep an eye out for it.) The light shifts dramatically depending on which room you’re in, so build in a few minutes to move around and find the spots that work for the look you want.
Off Color Brewing Mousetrap Taproom
From the conservatory we drove over to Off Color Brewing in Lincoln Park. JD and Josh picked it because they’re regulars and because the vibe is exactly right for them — exposed brick, industrial bones, mural on the side of the building, beers they actually wanted to drink. We grabbed pints, sat at the bar, hung out outside in the alley by the brewery’s signage, and just let the session breathe a little.
This is one of my favorite second-location moves for engagement sessions: pick a place where the couple actually hangs out. The photos end up looking like them instead of looking like an engagement session. JD held her beer like someone who’s done this before. Josh laughed at her between sips. We saw, for the record, several extremely cute dogs go by.
If you’re looking for a Chicago brewery for your own session, Off Color is a great pick — relaxed, photogenic, and the staff didn’t blink when we set up for portraits. (As always, it’s worth calling ahead anywhere you want to shoot at to make sure they’re cool with it.)
A Few Thoughts on Doing It This Way
A lot of couples I talk to ask whether it’s worth doing an engagement session at all. My answer is always yes — especially if you’re doing a destination wedding like JD and Josh.
When your wedding is somewhere far away, with limited time and a small guest list, you might not get a lot of relaxed, just-the-two-of-you portrait moments on the day itself. An engagement session back home gives you that — a chunk of time dedicated entirely to the two of you, in places that actually mean something to you, with photos that document this specific chapter of your relationship.
It’s also a good chance to get used to being photographed before the wedding day, which makes a real difference if you’re not naturally comfortable in front of a camera. By the time the wedding rolls around, the photographer isn’t a stranger and neither is the experience of being directed.
For JD and Josh specifically, this session also serves as a kind of love letter to where they built their life together — their dogs, their friends, their favorite brewery, the rhythms of home — before they head out to actually get married. I think that’s a really nice way to do it.
Two Locations I’d Recommend Without Hesitation
If you’re a Chicago couple planning your own engagement session and looking for ideas, both of the spots JD and Josh picked would absolutely work for you too:
Lincoln Park Conservatory is the move if you want lush, romantic, slightly editorial — think gardens, glass, soft light, and a green backdrop in any season. Free, public, and consistently beautiful.
Off Color Brewing is the move if you want casual, character, and a place that feels like real Chicago — exposed brick, beer in hand, outdoor space, a vibe that doesn’t take itself too seriously.
Both together make a perfect arc: green and quiet first, then loosen up with a beer.
JD and Josh — congratulations again, you guys are the best, and I cannot wait to see the wedding photos. Anyone else planning an engagement session in Chicago? I’d love to hear from you.
Looking for more Chicago engagement and intimate wedding stories? You might also like Kait + Jake’s Chicago sidewalk elopement and Nikki + Kate’s Chicago City Hall elopement.
Hiiiii, I’m the imaginative force behind Cooper’s Mill Photography—capturing your unique and magical moments with a touch of enchantment.
