Ashlyn and Kasey

How We Met

Kasey and I met Junior year of high school in Chemistry class (2011). Throughout the year we became Facebook friends and Kasey started to message me. Although I always left him on read, I decided to message him back and we eventually exchanged phone numbers. After several months of conversation and helping each other with homework we became friends. When our teacher allowed us to pick our own seats one day in class, I asked Kasey to sit next to me. We were just friends for a while but after much persistence from Kasey our friendship grew to much more.

Engagement Proposal Ideas in Havana, Cuba

Kasey eventually gained the courage to ask me on our first date, which happens to still be one of my favorite dates; we went to the movie theater to see The Lucky One. Through lots of shared laughter, random flowers on my lunch break at work and ultimately seeing the compassionate person Kasey is, I began to realize not long after that he meant so much more to me than a friend. We graduated high school together in 2013 and our relationship became more permanent. One day we went to have lunch at Panera where Kasey asked me to be his girlfriend; June 10, 2013, started it all and the rest was history.

Proposal Ideas Havana, Cuba

How They Asked

One thing Kasey and I both enjoy is traveling, we have always prioritized seeing the world together. Birthdays are very important to Kasey and with his 24th birthday right around the corner, I figured a trip to Cuba would be the perfect getaway. We booked a 5-night cruise to Cuba, although, he constantly insisted that he did not want this as his birthday gift because he knew he had a trick up his sleeve (as always). We have been talking about going to Cuba for the longest time. Before embarking the ship, Kasey told me he booked a private tour with a photographer while we were in Cuba to show us around the city and requested I bring a nice dress so we could do photos for his birthday. On October 26, 2019, the day after his birthday we arrived at Havana, Cuba.

The captain was having issues with clearance to get everyone off the boat and this delayed our exit when departing the cruise ship. While waiting in the security line, I noticed Kasey’s ears turning red, he seemed so anxious. I was making fun of him for it and didn’t realize why he was ultimately so nervous. The delay trying to get off the ship made us late to meet with the photographer and start our day. When we finally got off the ship, the photographer was gone. Kasey began to feel hopeless but was still determined to get ahold of the photographer. Having no cell service, he began to ask locals to borrow their phones. I started to get impatient and didn’t truly understand why it was so important to him to find this photographer.

Ashlyn's Proposal in Havana, Cuba

We decided to book a different tour and enjoy our experience in the historical country. After a few hours of touring the beautiful city in the heat, we got lunch before going back on the boat to relax for the rest of the day. Kasey suggested there was one more place that would complete this adventure, the Havana Cathedral. Thinking fast and improvising without the photographer, he asked me to take a picture saying he could set it on a timer.

He propped up our camera on the tripod and instead put it to record to capture the moment. As we were posing in front of the Cathedral, my boyfriend/best-friend was down on one knee, he popped the question; HE ASKED ME TO MARRY HIM! In so much shock, I said YES! After a day filled with riding around in classic cars, site-seeing and an unforgettable proposal; half of our hearts are still in Havana.