Winter Park Rain Day Proposal

on November 30, 2023
in Marriage Proposals

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Winter Park Rain Day Proposal

Jasuan + Josie's Engagement | Kraft Azalea | Winter Park, FL

We love a great Winter Park proposal story, don’t you? When we heard the beautiful story, we knew that we wanted to feature Josie & Jasaun’s Winter Park rain day proposal story.

Share with us when and how you met each other.

We met back in 2017 while at Illinois College. Jasaun was friends with my college resident advisor and one night he crashed our hall meeting, where he introduced himself. A year of friendship, movies, late-night Taco Bell, college parties, and laughs turned into much more.

We began dating in 2019 during my (Josie) senior year at Illinois College. Later down the road, we found ourselves relocating to Orlando, Florida in 2021 to complete graduate school & pursue our careers. Our love has continued to grow in Orlando, Florida where Jasaun proposed on October 1st, 2023.

What are your favorite things to do together as a couple?

Pickleball, working out, trying new foods and restaurants, dancing, karaoke, watching bad reality TV on Netflix.

How long were you together before getting engaged?

4 years

Did anyone help with the Winter Park rain day proposal?

Mackenzie Ayn Photography & Imago Dei Photography

Share your marriage proposal story…

I woke up Sunday morning and it was pouring down rain, I said “Wow it is really raining hard today!” Jasaun nervously asked “It’s raining?? That’s great.” as he nervously laughed. I had a feeling he was asking that day because he convinced me to wear a white dress to church that morning and he was so nervous about the weather. We went to church that morning and he immediately wanted to leave right after service, as he seemed in a rush.

I kept my cool and tried to just stay relaxed, because I knew he was truly freaking out on the inside. He told me he needed to take me somewhere to go ‘talk’. I knew it was happening at this point, but just went with the flow. He drove me to Winter Park, and after about 15 minutes I could tell he was stalling. I figured it was because of the weather his proposal idea wasn’t going as planned; so I just stayed quiet and let him do his thing.

We finally arrived at Kraft Azalea park, and it of course was still raining. We walked up to a bench where there were two clear umbrellas. He handed me an umbrella and he took one as well. He got down on one knee and asked me to marry him in the rain; which ended up being so unique and beautiful. Photographers Mackenzie and Darious caught all of it on camera for us, and we continued to finish the rest of the proposal session in the rainy weather with our adorable clear umbrellas.

Although Jasaun didn’t think it went perfect, in my eyes it was perfect for us! Jasaun then surprised me with a brunch celebration in Winter Park with our friends and family; including my parents and best friend (both from Illinois) flew into surprise me. The day was perfect in every way, and I felt so loved and joyful the entire day!