Tyler and I first matched on the dating app Bumble in 2021 after both of us were going both going through breakups. We quickly realized neither of use were in the right spot to be dating and we stayed in contact as friends. I ended up back in a different relationship the time and so therefore we lost contact. Fast forward to Spring of 2023 where we were both single again. I came across his profile again on Bumble and we reconnected and finally had a chance to build on the friendship we had already established. Tyler officially asked me to be his girlfriend at the first Bears' game of 2023 (and my first Bear's game!) on September 10th.
Tyler and I had a week long cruise planned to the Caribbean with my family (Mom, Dad, and brother Luke) in February 2025. Tyler had never been on a cruise, so I was so excited to show him a good time. This was also his first time out of the country! It was wonderful to have a warm trip planned to get out of the cold Chicago winter. Our trip started off strong with a beautiful night in Old San Juan, PR, where we explored a city none of us had been to. The next day, we boarded the ship and were off! We enjoyed our first few nights, celebrating Luke's birth on the second night. Tyler had originally wanted to propose the day after Luke's birthday (the 10th, which would have been 1 year, 5 months of our dating anniversary), however, I was feeling a bit seasick that evening. He improvised and planning a lovely surprise the next evening after a fun day in Barbados. My mom told me that she wanted to get a drink prior to dinner at this one spot on the back of the cruise ship that had live music playing and was a beautiful lounge spot. I met her there and then the rest of my family and Tyler showed up a few minutes later (Tyler stated he had to finish getting ready). Once we were all there, Tyler suggested we take a picture over on the side of the boat with the sunset in the background. My family followed us over there to take the picture (this should have been my biggest hint), and as I was trying to find the right angle, Tyler got down on one knee. I was definitely surprised and it all happened so fast! We had a fun crowd get to witness the semi-intimate moment and even had a fellow cruise passenger bring us two glasses of champagne immediately following the moment. That night, we had a lovely dinner show that was "rose" themed and vaguely resembled Romeo and Juliet. There was free flowing champagne and rose pedals everywhere and we even got a special "love potion" brought out to us. Cruise passengers recognized us all night and continued to congratulate us. It was truly a special evening.