Relaxed Downtown Winter Garden Engagement Session at a Brewery

Boy, do we have a fun Downtown Winter Garden engagement session for you today! My dear friend and former trainer, Katie, is officially getting married to the love of her life, Chris. I couldn’t be more excited for the two of them!! We took them to Downtown Winter Garden to capture their love at a few very meaningful places to their relationship. But first, you need the backstory!

Katie and Haleigh

My relationship with Katie started back in 2016. I was straight out of college and started my short-lived career with Disney. I was assigned to the show, Fantasmic, and my life would never be the same. The first person I met that day at Fantasmic would be the person I shadowed for the day. That would be where Katie entered my life! I followed Katie for the day, learning the ropes, and getting to know her a bit better. It turned out that we both started in theatre in the lighting department and we had a mutual friend in one of my other clients, Nick!

Over the next few years, after the Disney journey ended for us both, we would see each other at a few weddings. Katie was a bridesmaid in one and the planner of another. She even saved my clumsy self when I broke my ankle stepping out of a limo at the very beginning of a wedding day! I truly wouldn’t be where I am today without Katie. Seeing her finding her true love and being able to have the wedding of her dreams makes my wee heart so happy. We are so excited to be a part of it and to start celebrating with this Downtown Winter Garden engagement session!!

The Beginning

Katie and Chris first met in their high school theatre program. Chris was building sets and Katie was on lighting. They were always friendly with each other and spent all of their time in the same places with the same friends, but Katie didn’t care much for Chris back then. They both went their separate ways for college. Chris travelled to North Carolina to study theatre, computer science, and beer pong at a prestigious private college, while Katie stayed in Orlando to start her career in entertainment.

After Chris graduated, he came back to Orlando to visit his mother. With some other friends from high school in town, they decided to throw a party. Katie and her friends heard Chris was in town and invited him, and they reconnected then- only this time he was cute, fun, and smart and Katie simply had to have him. Katie and Chris started seeing each other casually, but they knew it would come to an end because Chris was headed to Texas to start working. They still talked a lot after he left, until one day Katie freaked out and straight up ghosted him for someone else.

Katie Moves Home

After a few years of not talking, seeing other people, each moving around the country, Katie found herself driving home to move back to Orlando all alone and, not uncommonly, thinking about that Chris guy. So, she did what any true Millennial would do and called her best friend from the road (their wedding officiant!!). Katie said “Richard, I’m driving back to Orlando. I don’t have a job or a place to live when I get there, but I’m going home. Could you please stalk Chris on the internet and find out if he’s seeing anyone?” Richard said “Of course, I’ll call you back” and he reported back with the lovely news that Chris was in fact, recently single.

Katie texted Chris out of the blue, completely disrupting his life in Ohio, and they started talking frequently. A few days later, while planning a trip to Costa Rica for her cousin’s wedding, Katie (jokingly) said to Chris “I’m expected to show up with a date. Do you want to come to Costa Rica with me?” Chris replied, “I hope you weren’t joking because I just bought a ticket!” They met at the San Jose International Airport and they haven’t looked back since then!

The Relationship

Katie and Chris’s relationship is special for a lot of reasons. Some people just fit into your life so perfectly you can’t ignore it. They always have a good time together, whether they are off someplace fabulous on a trip or just sitting in their living room playing board games. They’re always having a laugh and plotting big ideas for their future together. Katie and Chris brew beer at home together and they spend a lot of time cooking up recipes and sending beer off to competitions. They hope to someday open their own brewery. Katie and Chris are always pushing each other to take big steps because they know they can make it through anything together.

The Proposal

Chris proposed in their living room on Christmas morning. It was so sweet and well-planned! Katie said it would have been a perfectly executed surprise if he hadn’t looked at her hand two days before and said “You’re going to paint your nails before Christmas, right?” Ugh. Boys. To be fair, Katie is an AMAZING scenic and props designer, so paint is part of the deal!

Katie’s Nana makes stockings for everyone in her family when they’re born or when they marry into the family. The stockings are frequently a wedding gift when someone marries into the family and it’s a really sweet tradition. Every year it’s hung on the mantle, and every year from her Nana, they all get the same things in our stockings- a new toothbrush, toothpaste, hand sanitizer from Bath and Body Works, and some scotch tape. One year, Katie asked her mom if she could have her stocking at her house. Katie’s mom told her she couldn’t have it until she was settled into a home and married so that Katie wouldn’t lose it. She wouldn’t let Katie have her own stocking!

On Christmas morning, the couple was opening presents with Chris’s family. After everything was opened, Chris pulled out Katie’s Nana stocking, and inside was all of the family traditions, plus a ring box. It was the sweetest thing anyone had ever done for Katie. Her mom knew about it because she gave him the stocking a few days before. Katie said it was really fun to call her afterwards and pretend that nothing happened. She told her that she got a really nice food processor for Christmas while her mom tried not to spill the beans!

The Ring

Katie and Chris had her ring custom built together after Katie fell in love with the place holder proposal ring. They found the ring at a vintage/estate jewelry shop in Winter Park. It has two pieces that fit together. The ring was an old vintage yellow gold and all diamonds, but the couple loves bright colors far too much to let that be it! Katie and Chris had it plated in white gold. They replaced the center diamond with purple/blue opal that changes colors in the light. It is surrounded by a band of diamonds, and they replaced the diamonds on the little ring with bright red rubies. They are going back before the wedding to make a third ring that fits into these two as a wedding band!

The Downtown Winter Garden Engagement Session

Since Katie and Chris are huge into breweries and the downtown vibe, we all figured that Downtown Winter Garden would be the best place for their engagement session! With the Crooked Can Brewery, a gorgeous and small downtown view, and a theatre to tie it all together, it was the perfect scenario. We started our session at the brewery, letting the couple relax and feel at home with one another. The two cracked jokes over their beers and enjoyed being in the company of one another. The manager of the Crooked Can let us in to the closed Barrel Room to capture more intimate moments of Katie and Chris together.

After our adventure through the brewery and Barrel room, we walked the streets of Downtown Winter Garden, eventually ending up at the Garden Theatre. As you may have seen from our Instagram stories, Jack frequently sound designs at the Garden Theatre! They were gracious enough to let us sneak in for a few photos in the empty theatre. We really wanted to showcase where Katie and Chris met and what brought them together. It was a wonderful way to end their Downtown Winter Garden engagement session!

Katie and Chris, I am SO excited and thankful to be on this wedding journey with you. This may not be our first wedding together, but it will be the most special now that it is YOURS. We cannot wait to celebrate with you at the Lightner Museum in October. Bring on the year of wedding planning!!

Take a peek at their Downtown Winter Garden engagement session below. Plus, a HUGE thank you to the Crooked Can Brewery and the Garden Theatre for allowing us the space to capture Katie and Chris’s Downtown Winter Garden engagement session!