We love when a marriage proposal has the element of surprise, don’t you? When we learned that this particular proposal had a very sweet second surprise for the unsuspecting Lauren, we knew that we had to feature the story of Lauren and Anna’s surprise proposal in Winter Garden.
Photo by Crystal Photography LLC
Share with us when and how you met each other.
How we met is just another typical online dating story. In November of 2021, Anna swiped right and I matched with her on Hinge. To be quite honest, I was at a rough point in my life and wasn’t even sure if I wanted a relationship at the moment so I didn’t really give her the time of day.
She was persistent though, and the more we talked, the more I realized the calming affect she had on my life. I’m not sure if it was out of pity or what, but after spending Thanksgiving alone, Anna asked me out on a date the Monday after.
With nothing to lose, I said yes.
She thought I was going to bail all day but to her surprise, I met her in Winter Garden, FL for dinner. After dinner, we went to the bar next door and talked and laughed and cried until we closed the place down but that wasn’t the end.
I walked her to her car and we stood in the road talking in downtown Winter Garden, until we forced ourselves to go home. I know we both could’ve stayed there all night but don’t worry. I drove to her house the next day for date #2 and the rest is history!
What are your favorite things to do together as a couple?
We love anything and everything to do with sports. We watch them on tv, attend games, and even play them ourselves. We love spending time with our dog, Tatum, and taking her on adventures.
Most of the summer is spent on the water, fishing, swimming, or floating. We enjoy traveling as often as possible like trips to Tulum, St. Louis, or Arkansas to visit my family. Anna also enjoys reading, photography, and forcing me to workout with her.
How long were you together before getting engaged?
We were together for 14 months before getting engaged.
Did anyone help with the surprise proposal in Winter Garden?
Tamra Crystal @crystalphotographyllc and our friend, Madeline Wright.
Share your marriage proposal story…
Proposal planning began in October of 2022. Anna and I had already gone to look at rings together so it was time to get the ball rolling.
I wanted to do something special to document my perspective throughout the proposal planning process so I decided to document all the important days leading up to the proposal by writing letters to Anna in a journal that she could read after.
But before planning the proposal day, I needed to get the ring. So, I may or may not have taken an extra long trip to get my car serviced in order to pick out the perfect one without Anna knowing.
From then, the proposal planning took off. I knew I wanted to take it all back to the place we first met in Winter Garden, FL. I picked an even numbered date (just like Anna would want) in January and invited our closest friends and family.
Photo by Crystal Photography LLC
Unfortunately, our parents weren’t going to be able to make it but that didn’t stop the plan. On the day of, I took Anna back to the bar we closed down in Winter Garden on our first date. I was so nervous, I’m certain she could tell.
In the meantime our friend, Madeline, and our photographer, Tamra, were getting everything set up by the fountain. A basket with the journal, an engraved bottle of champagne, and the ring were waiting on us as we walked up the steps.
Photo by Crystal Photography LLC
I think I blacked out because all the people around, didn’t even phase me. I read the poem on the last page of the journal and I can still hear her voice in the background saying “Holy Sh*t!” I was almost to the end, the most important part, when she told me how beautiful it was but I was quick to let her know that I wasn’t done yet.
I pulled the ring out and asked her to marry me and of course, she said YES!
We were quickly surrounded by our people who were ready to celebrate and Tamra who was excited to capture the moment. We continued taking photos with Tamra across downtown and then headed back to meet our friends for dinner.
Photo by Crystal Photography LLC
One last picture was captured and when she turned the camera around for us to see, and I almost collapsed. I had the whole day planned. Every detail. The only one being surprised was Anna.
But in the background of the photo, there stood my parents who drove 14 hours through the night from Arkansas to surprise both us on our happiest day. It was the cherry on top. I couldn’t have asked for a better engagement day with the love of my life.
Photo by Crystal Photography LLC
What was the best moment of the proposal?
The best moment has to be when Anna interrupted me mid proposal and I had to tell her, “Wait! I’m not done yet!”
Photo by Crystal Photography LLC
Who did you tell that you were engaged first?
The first person I told was my brother, Logan.
Tell us about the ring!
The ring is an emerald cut with halo that was custom ordered from International Diamond Center. It has a blue sapphire on the inside of the band that can be used to signify “something blue” on our wedding day.
Photo by Crystal Photography LLC
I’ve been surprised by how much you have to pay attention to every little thing that goes into wedding planning.
I’m enjoying getting to dedicate special time to planning a wedding together.
What are you most excited about wedding planning?
Anna is most excited about the music and I’m most excited about the food because those are two things we love. We also enjoy spending this time together, planning a day to celebrate our love.
Photo by Crystal Photography LLC
If you’ve already decided, when are you getting married and what is your venue?
February 4, 2024 at The Garden Villa in Winter Park, FL
Why did you choose that venue?
The Garden Villa has the outdoor and indoor spaces we desired along with an intimate vibe that would allow us to truly enjoy the day with all of our guests.
We are expecting 100 guests.
Focus on the big things first and prioritize the most important smaller details next that we both want.
Modern and minimalistic.
Photo by Crystal Photography LLC
Have you selected any other vendors for your wedding?
💚 DJ – Our DJ Rocks @ourdjrocks – DJ Jazmin @djjazminrocks
💚 Catering – Cocktails Catering @cocktails_catering
Live Event Painter – Sam Nelson Art LLC @samnelsonart
Photography – Tamra Crystal Photography @crystalphotographyllc
Don’t be afraid to start early. Also, it is your day so plan it how you want it. Don’t be afraid to tell people no.
Congratulations Lauren & Anna on your surprise proposal in Winter Garden!
Want to feature your proposal? CLICK HERE to submit your story!
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