Caitlin and Henry

Engagement Proposal Ideas in Clearwater Beach, FL

How We Met

Henry and I met working at Pizza Hut. I worked there for 5 years through high school/college and other jobs. Henry was well worth staying there all that time! I still remember exactly where I was sitting in July 2014, who I was talking to, and what time of day it was when I first saw him walk in. I was dating someone else at the time. Over the next 6 months, he teased me relentlessly in a poor attempt at flirting but always kept me laughing. He won my family over when they would visit the restaurant and he would sit in the booth with me while I ate on breaks telling our coworkers we were on a date. When he found out my previous relationship ended, he gathered our male coworkers and bet that he would win my heart, saying “may the best man win!”

Marriage Proposal Ideas in Clearwater Beach, FL

I would say he did!

How He Asked

Our special friend, Britny, passed away suddenly in a tragic accident last May. Henry and I immediately made plans to visit her hometown in Florida over the summer to keep in touch with her boyfriend, Nick. The night before our flight I ended up in the ER with mono. It was devastating! We had to reschedule for the end of September. Little did I know that trip, which I believed would only provide me with spiritual closure over the loss of our dear friend, would soon become even more special.

Henry and I were so giddy like little kids when the trip finally came around. It was his first time flying and as soon as we landed we took off up the coast to Britny’s hometown. We visited her gravesite under the stars and left behind a gift before having dinner at a nice seafood restaurant right on the bay. We stayed at the cutest Airbnb and spent the entire next day at Universal Studios. We had the energy of 5 year olds I swear! The third and final day was saved for the beach. I’m a bit of a control freak so I had already booked us stand up paddle boarding and a sunset cruise. However, Henry let me know that he also had somewhere he wanted to take me as a surprise based on our local friend’s recommendations. Dolphins frolicked all around us playfully while paddle boarding. It was so surreal!

Henry said we should go ahead and get ready for our sunset cruise before my surprise. Unbeknownst to me, I ended up getting ready for our proposal at Planet Fitness! Which very much fits our active lifestyle. I was so confused when we pulled back up at the same beach we had just left. I noticed Henry had been on his phone quite a bit but assumed he was just getting directions to the surprise location.

Little did I know, he had hired a photographer at Honeymoon Island where he planned to propose. Sadly, the photographer let him know that the beach was not very pretty that day and covered in rocks and seaweed. The photographer refused to drive anywhere else so Henry was busy all day enlisting the help of our friends from the area. They blocked me from a Facebook status begging anyone to help with a beach proposal. The young boy that accepted the offer went well out of his way, driving hours all over to find the perfect spot and gather supplies. Henry acted frustrated at this time like my surprise had fell through and asked if I just wanted to walk on the beach. It was scorching hot and I had just fixed my hair and makeup, but I obliged and tried my hardest not to complain.

We walked for a while in the sand when Henry started pointing out towards a boat on the horizon asking me if they were tubing. I turned my head out towards the water while he pulled me up the shore and when I looked back up there was a huge heart in the sand that said “CAIT WILL YOU MARRY ME?” complete with roses, crowds of people cheering in the water and on their balconies, and the kind stranger boy recording. To top it off he proposed with my late mother’s diamond ring. It could not have been more perfect and we had a sunset cruise to celebrate!

Our Video

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Special Thanks

Caitlin Whorton
Photographer
Heath Whorton
Videographer