How We Met
He was the Best Man and I catered the dessert table. So, to start off, we met through mutual friends (now ex-best friends but still grateful!) that ended up getting married! His best friend and my best friend at the time moved from PA to FL and Dylan was their go-to friend when they were up in PA. Once they made the move, I met her through working at Disney & I became their go-to hangout friend when they moved to FL. They eventually became engaged and asked me to cater their wedding desserts & cookie table (a Pittsburgh tradition) for their wedding. I initially met Dylan while traveling up for their wedding in Pittsburgh and he was the best man. I thought he was super hot & good-looking and I was single, by myself at the wedding but nothing really transpired.
Some time passes so, naturally, there were a lot of times they would invite Dylan down to FL and we would all go on mini-trips together as a group. Our first trip together was spending the 4th of July weekend at Disney’s Hoop-de-doo Revue. After bottomless beer & sangrias later, there was a brief moment during the show where there’s crowd participation with swinging napkins in the air and just a ball of fun, where he was looking over at me & gave me “the look” of that this is the person I want to be with. It was like the movies & so cheesy!
On one of our (last) road trips with them to Myrtle Beach, it was at the point where I & Dylan were talking back-and-forth but nothing was specific or “titled” so this frustrated our friends a lot (because it was sooo obvious that we wanted to be together & we were “official” without being “official”). One night, they got so frustrated that they bugged us constantly with “DTR! DTR!” (which means ‘define the relationship’), and at that moment, Dylan gets up & just screams “We are in a relationship! Kelly, get dressed, I’m taking you out on a date.” At that moment, I just thought, “Wow, now that’s a man that knows what he wants and isn’t afraid or ashamed to profess that he wants me.”
And the rest is history!
How They Asked
So we were at a point in our relationship where it was a pretty low point. I recently got laid off from my lab job, we were at a pivotal point where we were not sure if it’s feasible to get married and stresses from outside sources were just getting to us individually & as a couple. So, in the midst of this, Dylan planned a secret trip for us to go on for a week. All I knew about it was to pack for warm weather & that’s it! He kept the location, tickets, EVERYTHING a secret! That’s a feat in itself considering I am the kind of person where I ruin surprises (in a good way!). Also, in the midst of the pandemic still going on but places are starting to open up, he kept the reason for getting a COVID test from me as well.
I remember I didn’t find out till we got onto the airplane & they announced “Going to St. Croix”. He even sat us facing away from the gate, where it says the location while waiting to board so I didn’t see it! So sneaky! We land in St. Croix & our first night was spent in this normal hotel with no AC. I, for some reason, didn’t complain & was just happy to be there with him. On our next night and so on, he surprised me with our “actual” resort which was this amazing place on top of a cliff overlooking the crystal clear ocean in this 5-star suite! It was all a part of his master plan!
After excursions, sunbathing, & just enjoying island life, it poured down rain on the 4th day (which was the original day he planned to propose on the beach) and I recall he was on the phone with the hotel manager multiple times and he was visually frustrated. He just chalked it up to a dinner reservation and he was trying to get us a table. Little did I know, he had it planned with a photographer & a 4-course dinner in a cabana on the beach but couldn’t do that (since the monsoon that was happening).
On the last day, he said that we had a fancy dinner reservation at the resort and to get dressed up. This wasn’t out of the ordinary since we love going to fancy dinners from time to time & we are big foodies! So, got dressed up and he said “let’s take photos on the beach.” I should have known by then there was something fishy about this because he’s not a photo-social media type of person but I just thought, “Hey, he’s being nice and has a change of heart since we are on such a gorgeous island.” He took me on a walk on this private part of the beach and he was trying to get further down but I, all of sudden, yelled “OMG, WE ARE GOING TO BE LATE FOR OUR DINNER!” So, I start running back up the opposite way towards the resort and he just yells “KELLY!” and in anger, I turn around and I’m like “WHAT!?” And there, on one knee, he was gripping something in his hands, and with tears in his eyes, he popped the question.
It is so true when they say you blackout because I don’t remember a thing he said! All I remember is thinking I was being punked then when the words “Will you marry me?” came out of his mouth, it immediately snapped me back to reality & I was like “Oh shit! this is happening! I am getting engaged too. OMG!” I said YESS and started hyper-ventilating on the beach then started crying. Moments later, the monsoon of rain came again and we got caught on the beach in a rainstorm. We were drenched by the time we got to dinner & he had that 4-course meal with personalized menus & candlelit dinner waiting for us. It was, by far, the most thought-out, romantic, totally “us” way he could have done it. I joke with people now that I said yes to marrying him & not the ring because he was so nervous, he took the ring out of the box & had it in his pocket while taking pictures on the beach, he was afraid it was going to fall out or he was going to drop it in the ocean. So when he did propose, he was gripping it sooo tightly that he covered up the ring. I didn’t see it until it was put on my finger!