At WedVibes, we’re always drawn to the stories behind the aesthetics—the vision boards, voice notes, and late-night Pinterest scrolls that quietly shape iconic wedding moments. So, we did what we do best: reached out to real brides who are planning weddings their way. From spontaneous proposals to guest lists made on Google Docs, these brides are rewriting the rules and curating celebrations that feel less like tradition and more like self-expression.
In this series, they open up about the moodboards they can’t stop tweaking, the TikTok trends they’re into, and the vendors who just get it. Expect real love stories, real planning highs (and lows), and plenty of inspiration for your own “main character” moment.
Meet The Couple
Jack and Maddy live in Chicago. He works in private equity real estate, she’s an energy broker. Between the two of them, life revolves around yoga, spontaneous trips, trying new restaurants, a good documentary or a night at the movie theater, watching the sunset, lakefront bike rides, the occasional round of pickleball, and Goose, their dog.
How did you meet?
Jack was technically my first boyfriend in 5th grade, even though we never actually spoke. I eventually had my best friend Margot break up with him on a three-way call—he thought it was me. We stayed in the same friend group through middle and high school, went to prom together senior year, and then lost touch. I went to FSU and moved to New York after college. He went to Wisconsin and ended up back in Chicago. Eight years later, I came home for my friend Summer’s birthday. We met up with all our old friends, including Jack, and we’ve been together ever since.
The Proposal
We had a Bali trip planned for late October 2024, so I was convinced it was happening there. Instead, he proposed on my birthday, October 3rd, while we were walking home along the Chicago River. Our families were waiting at our apartment with food and champagne, and my mom put Goose in a tux. I was still in such shock. Waking up the next day with all my family was the best feeling. That night, he threw a surprise party with all of our friends + family. My 2 sisters bought me 3 dresses to choose from (bless them). It was the best weekend, I wouldn’t change a thing.
The Wedding Vision
1. When and where is your wedding taking place?
August 2026, at Theater on the Lake in Chicago – the same place we rekindled in 2022.
2. Describe your wedding in 3 words.
Effortless, Chic, Cinematic.
3. What are three non-negotiable elements for your big day?
First look down the aisle – We want a raw, emotional moment to happen in real time, nothing staged.
Fun, unexpected experiences – No tacky traditions or stiff vibes; we want it to be fun and emotional. We want a sax guy on a table to start the dancing, joints/cigs/cigar bar, no massive wedding cake.
Intentional design + florals – Nothing preppy or overly floral. I want it to feel like an intimate speakeasy, long tables, candlelit, romantic with an edge and energy.
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Planning Process
1. What’s been the highlight of your planning process so far?
Pinteresting and figuring out how to build an experience and not just a wedding.
2. What’s surprised you most about wedding planning?
How many details exist that you’ve never noticed once as a guest and suddenly you have strong opinions about all of them.
3. What’s one piece of advice you’d give to someone just starting their planning journey?
Take your time. You don’t need to race to the altar. Use the in-between to be intentional and actually enjoy it.
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