Cassie and Pierce

Cassie's Proposal in Alali Restaurant in Santorini, Greece

How We Met

Pierce and I met through a mutual fund who I went to college with at The University of Tampa. For years, I only knew Pierce through FaceTime and stories until he eventually came down to visit and even after that, we remained friends for a while. About 3 years into our actual friendship, a group of us went to California for Halloween and while we both kept our cool throughout the trip, it was then that we both realized that we liked each other. Of course, I played the “not-looking-for-a-relationship” card at first but that didn’t last too long!

How They Asked

Pierce and I went ring shopping in NYC during Christmas of 2018 but he kept me on my toes for almost 9 months as he proposed on our trip to Greece in September of 2019. A few weeks before our trip Pierce drove to New York for what I thought was business but was really him going to ask my parents for permission to marry me. On our vacation, we first spent time in Athens before heading to Mykonos, where he still hadn’t proposed and then ended our trip to Santorini. We made reservations at this beautiful cliffside restaurant months in advance and scheduled it for the second to last night of our trip. We chatted throughout the hour-long ride to dinner and I discreetly scoped out Pierce’s pockets but didn’t see any sign of a ring.

At this point, I was starting to lose hope that it would happen while we were in Greece. We had some appetizers and our server, Olti, asked if we wanted a sunset picture but told us he’d take later when it was a little darker as well. He started taking what I thought were pictures and Pierce started kissing me, which he never does for photos, but I went with it. I then felt him going in his pocket and finally caught on to what was happening! As corny as it sounds, the world truly stopped for a moment when he got down on his knee and asked me to marry him. The fireworks that went off right after I said “of course” were truly the icing on the cake!

Engagement Proposal Ideas in Alali Restaurant in Santorini, Greece

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