Kaitlyn and Dylan

How We Met

Dylan and I first met during my freshman year of high school. I’ll be honest, at first I wasn’t very interested and at the age of 14, in the midst of my awkward phase, I was far too nervous around him to even function. However, he was very persistent, and eventually, he became my first boyfriend (and first kiss). We both still had lots of growing up to do, so after freshman year, we went our separate ways. The second I started seeing someone else, Dylan told me that one day if that didn’t work out, he wanted one more chance with me.

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The rest of high school we were with other people and our relationship pretty much boiled down to a “hey” every now and then. Flash forward to college, I had just broken up with my boyfriend from high school and got a message from Dylan (he was ready for that second chance!). We set a date to reconnect over my winter break when I was back in our hometown and then spent practically every day together, and on January 1, 2014, he officially asked me to be his girlfriend. Now, looking back I’m so grateful for the time we spent apart to grow and have so much appreciation for the path we’ve been on since 2014.

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How They Asked

Dylan knew that I wanted to wait until I graduated from college and my master’s program before even THINKING about getting engaged and married. I finished my master’s program in May of this year and we moved in together 2 weeks later! I was so excited to finally live together and start a new chapter of our relationship. It then very rapidly hit me how ready I was to get engaged! We’ve talked about it for a while but never looked at rings in person. Dylan originally never wanted to pick out a ring together, because he wanted it to be very traditional and a complete surprise, but one night he told me we could go check out some rings. Well, I was READY. Two weeks later, we were in Diamond’s Direct picking out rings together! I should’ve known that was only going to make me THAT much more impatient. From then on, it was pretty much the only thing I talked about to my friends and family (grateful they humored me!). Eventually, because I couldn’t let it go, he broke down and told me he had the ring. I felt better knowing that it at least COULD happen soon, but I had no idea when. On the weekend of December 14th, we took a trip with friends and I was so sure it would happen then (I found out after the proposal that he had the ring that whole trip just in case!). Admittedly, I was a little bummed coming home not being engaged, but I did my best to stay present and appreciate our time together and with friends.

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Dylan knew that he was going to have to pop the question at a random time, or else I would have an inkling it was happening. Making plans is not his forte, so if he planned anything, I was going to know. I had just asked our friends if they wanted to go to a light festival on Christmas Eve, and he took it as a possible opportunity. He talked to our friends about the possibility of proposing that night and had the ring in tow just in case. As we were walking around, we came upon this light display with a giant diamond ring that said: “marry me”. My first thought was “Of course this would be here!” *eye-roll*. Dylan had no idea that light was going to be there, but immediately (and secretly) signaled to our friends that this was the moment. Our friends said we should take a picture under it and I thought they were just being cruel–they knew how bad I wanted this, how dare they make me stand here?! (hence my sass in the pictures above!).

PLOT TWIST! He then reached into his pockets and got down on one knee! I was so surprised–It was like little flashes of our journey to this point filled my mind and I was so overcome with emotion. Eventually, I was able to mutter “yes” through my tears. Our close friends were there to share the moment with us, which made it even more special and to have these pictures and the video they took to look back on will be something I will always cherish!

We got to spend Christmas Day sharing the news with our families and it was so much fun to see their reactions and celebrate! Christmas Eve will now hold an extra special place in our hearts & my first kiss now gets to become my last!

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