Sweet Outdoor Garden Wedding at Glessner House

The sweetest outdoor garden wedding for Cindy and Dennis was had at Glessner House. Chicago can be very tricky to secure an outdoor day, but these two successfully managed an outdoor ceremony AND reception! We wish we could always get that lucky with weather! Photographed by Winterlyn Photography.

The Proposal

“Cindy and Dennis were doing long distance between Detroit and Chicago. Usually, the trips to each other’s city would be planned ahead of time. Cindy was not expecting Dennis the weekend the proposal shenanigans started. Dennis gave Cindy’s two best friends a task to take Cindy out on a scavenger hunt. One of Cindy’s best friend decides that she wants to go shopping with Cindy and she makes a plan to pick Cindy up. But when Cindy comes outside to the car, her other friend was there. Usually, the two best friends do not hang out together. Cindy is very quick witted and knew something was up. The two best friends say that they have something to do with Cindy and it’s important to do it together. All of this is very suspicious of course. So Dennis is ahead of the two best friends planting these beautifully printed cards with a poetic riddle that he wrote. The best part is, the two best friends do not know the answers so they have to figure out the riddles with Cindy’s help, of course, to complete the scavenger hunt. They would have to confirm the next destination with Dennis if they had an idea of where it would be. Cindy usually just blurts out something random that she thinks is the answer. At the end of the scavenger hunt is the museum that Dennis asked Cindy to go two messages in on the dating app. And of course, as Cindy is running to the front of the Art Institute, she sees Dennis hiding in the bus stop. And Dennis is shocked that Cindy even saw him in there. It is Chicago so we have to be well aware of our surroundings. At the entrance of the Art Institute, Dennis tells Cindy that she is not getting proposed to because it is too easy. Instead, he hands her a plane ticket to go to New York as one of their trips for the year. The secret is that Cindy does not know Dennis invited her two best friends to go as well.

Okay fast forward, two months later. The trip to New York is another shenanigan that Dennis created on his own. Dennis makes it seem like a full friends trip and they even spend a whole afternoon walking in Central Park witnessing 3 proposals. Cindy gives up on the idea of a proposal at this point until they decide to walk under the Brooklyn Bridge. Cindy’s phone is dead so she borrows her friend’s phone. It had just rained and it was dark outside since it was evening. Dennis starts talking to these random people that he knows (nothing surprising) and Cindy minds her own business trying to take some landscape photos of the bridge. Then, Cindy noticed the guy that Dennis is talking to looks very familiar. It was one of their friends. This is where Dennis decided it was brilliant to go kneel down on one knee and take out a ring. The friend was there to photograph this moment. And this is the long story about how Dennis successfully proposed and surprised Cindy.”-Cindy & Dennis

The Wedding Vision

“We envisioned our wedding to be outdoors in Chicago with a very green environment. We are so lucky that we came across Glessner House while we were taking a walk in the neighborhood. We wanted to spend it with all of our closest friends and family. The venue exceeded our expectations with their ivy lined wall, and beautifully lit outdoor space. The unique wedding dress, from Grace and Ivory, turned out better than I expected with modern/classic vibes. The floral color palette came out to what I asked for thanks to Bunches Chicago! The food tasted better than the food tasting and I think everyone had as much as I wanted them to. Everything just falls into place on the day of.

We made our own wedding favors. We wanted to have something that would not take up more space in someone’s home or life. We had a tiny jar of bonne maman honey with two tea bags tied together with a ribbon. The honey was also a good touch for our venue as the previous homeowner of the historic home was a beekeeper.”-Dennis & Cindy

Advice to Engaged Couples

“Our advice is “do not procrastinate.”  We procrastinated due to COVID and the unforeseeable future. But we think everything turned out the way it should be. The wedding is about you as a couple and who you want to share that day with. We were focused on ourselves and everyone that we invited so we did not have a large wedding. The day was about us as much as it was about the guests. We highly recommend a day of coordinator if you are on a budget. But take some time out on your wedding day to have a moment between the two of you. And nobody knows if the wedding did not go the way you envisioned. It all falls into place on the day of.”-Cindy & Dennis