Kaitlin and Ryan

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How We Met

Ryan and I have known each other since we were little kids. My two best friends, who I’ve known since kindergarten, are his cousins and we all went to school together and played every chance we all got. Ryan is a year older than I am, so we always looked up to him and his friends as the “cool kids” who we would follow around nonstop. We always had a crush on each other, but were too young to take it as anything serious. Fast forward to our high school years (we still attended the same school together – yup, that’s 12 years!!) where we finally took the plunge and started dating! We dated for a few years, but ended up going our separate ways. P.S this was my first real heartbreak!!

Ryan went away to college in Philly, and I went to upstate NY the following year. We both would keep in touch occasionally throughout these years, but found ourselves in other relationships and moved forward with our lives. No matter how much time or history seemed to pass us, Ryan and I always found our way back to each other. We always found little reasons to chat, or check in on each other through our friends.

Four years later, after we both graduated college and were moved home (we also live around the block from each other, as if school and friends weren’t enough in common!) my friends started planting the seeds slowly but surely to get Ryan back in my life. They would tell me he was asking about me, and eventually would unknowingly have us both meet up at a family BBQ. At that point, I had just gotten out of a relationship and wasn’t really interested. I told my friends thanks but no thanks, and left the bbq. I got in my car and no less than 30 seconds later I had a text from him. We chatted on and off for a few days before he asked me to go to dinner. I told him I couldn’t – that I had to pick up a passport at my aunt’s house (I know – what a terrible excuse??!!! And IRONIC if you keep reading) and he replied, “Okay pick you up at 8”. He didn’t take no for an answer and I’m so glad he didn’t – four years later and here we are!

How He Asked

Two years ago, Ryan took me to Turks & Caicos to celebrate my 25th birthday. It was the most magical place we had ever been to, and we loved each and every second we spent there. We always knew it was somewhere we wanted to go back, and when my 27th birthday rolled around he planned a return trip! I was so excited to get back to our special place that we didn’t even think about a little thing called “hurricane season.” Our trip had been planned for months, and when we were 10 days out I did my normal weather check – a little cloudy but nothing crazy. A few days later the dreaded “Hurricane Matthew” was born. It quickly went from a tropical depression, to a tropical storm, and then to my horror, a hurricane. As if it couldn’t get any worse, it developed into a category 5 hurricane barreling towards Turks!

I begged Ryan to please cancel the trip and reschedule for a few weeks later so we wouldn’t travel all that way to be bunkered down in a hurricane. I was adamant on not going – nope, we would definitely not be going!! Little did I know I was trying to cancel my own engagement trip!! After much convincing and tons, TONS of text exchanges from my mom, friends, and future sister in law, we (or should I say ‘I’) decided not to cancel, to “look on the bright side” and have a good time rain or shine! After all, it was my birthday and this was our chance to sneak away for a week and enjoy each other.

Now- if you think that’s the bad luck, just wait. Two days before our trip (the trip I FINALLY was convinced to go on and make the best of) Ryan called me asking for my passport number. Ten minutes later he called me back and I heard the 5 words no one ever wants to hear 48 hours before a trip – “Honey, your passport is expired.” SILENCE. Panic stricken, I woke up at 5am the next morning and drove 3 hours Philly to beg for an emergency passport! It must have been my lucky day, because I got my passport that same day! Minus the whole little stage 5 hurricane issue, we were ready to go!

We got to Turks on a Saturday, and to our amazement, had the most beautiful blue skies all weekend! On Monday, it rained a bit during the afternoon and Ryan snuck away for a “work call” while we ate lunch under the umbrella waiting for the rain to pass. It was a quick shower and then sun came out right after – but we had to go get ready because Ryan set up a wine tasting at the hotel next door.

By 6:30, we were downstairs about to walk down the beach to the neighboring hotel for our romantic wine tasting. Magically, the skies had opened up and it was gorgeous out, just in time for sunset. We snapped a few selfies, and headed down the beach. As we got a little farther, I noticed a huge conch shell on the beach. Now if anyone has ever been to Turks, you know how cool these things are! I’m a secret shell lover and was bummed at the prospect of not being able to find one like we did two years ago because of the weather. Ryan assured me in the beginning of the week we would get one to bring home and so I was super excited when I saw one on the beach! I walked over to it thinking I could snag it as a souvenir when I saw something in it.

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I stared at the shell and what was written on it in big blue words, “Always have, always will”… our special phrase we said to each other. I don’t know if I was confused, stunned, or in shock, but in that moment I knew my life was about to change. The next thing I know, I heard all these people cheering and clapping, and I turned around to see Ryan waiting for me on a knee.

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I walked over, with tears in my eyes in disbelief. He told me how much he loved me, and said the sweetest words that I have been waiting to hear my whole life. Before I knew it, tears were flowing and the word YES was on my lips! We were engaged!!!!

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A few seconds later he pointed to the hidden photographer, who had captured our entire engagement.

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As if it couldn’t get better, on Friday, we started the journey back home to New Jersey, where he surprised me with a huge party of 70 of our closest friends and family waiting to celebrate with us! Oh and about that stage 5 hurricane, we didn’t even get any weather!

The moral of the story is that life doesn’t always promise you sunshine. It rains, it pours, and what’s most important is that you have someone by your side, who can dance in the rain with you. Throughout all these years, Ryan and I have danced in plenty of rain, but we never lost sight of each other. When something is meant to be, it always finds its way.

A stage 5 hurricane, an expired passport, and one engagement later – it was the best week of my life!

To my sweet fiancé – Thank you for making every single dream I’ve ever had come true! I love you endlessly – always have, always will.

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Special Thanks

Brilliant Studios
Photography