Holly and Jack
How We Met
I met Jack in a sort of unconventional way, I guess you could say. I saw a picture of him through a mutual friend back in early 2014 when I was a sophomore in college and thought to myself “Woah, he’s a cutie and those eyes (swoon)”. So, I did a thing…I looked him up on social media and followed him on, dare I say it, twitter. Soon after, he sent me a direct message (yes he slid in the DMs) and from there our relationship took off. To this day we still argue about who made the first move, I say him.
Jack plays football at a university that’s about an hour from the University of Kentucky which is where I was at the time so we were long distance and our communication mostly consisted of 3 hour long phone calls every night. I had never met someone who could make me laugh as much he did and who I already felt comfortable enough around to let out my inner weird. We were able to meet up in person for the first time a couple months later in which my first words to him were “Wow, you’re tall” (he’s 6’5). We really liked each other and everything felt so natural but I was intimidated by my feelings and the long distance and just the idea of a serious relationship at that time of my life. Jack was really upset and I’ll really never forgive myself for being a chicken.
When school started back in the fall I was feeling pretty down on myself. I had been thinking about Jack a lot and how I had probably just given up a chance with one of the best guys I had ever met. Just as I was considering reaching out to him he started dating someone else, which I only knew because of social media stalking of course. Lucky for me it was short lived and I was able to start talking to him again if he would have me. Also lucky for me Jack is the most forgiving person I know and he agreed to give me another chance.
We were still long distance and it was tough to get the ball rolling on an actual relationship with Jack playing football, me working and both of us full-time students. Towards the end of the year, we each lost a grandparent within a month of each other. Jack really helped me through the loss of my grandmother and I helped him through the loss of his grandfather. I think I can speak for both of us when I say that was a time we grew to love one another deeply without even being an established couple. When something bad happens and you find yourself running to a certain someone to make you feel better every time, it can be very telling.
However, it wasn’t until the end of that year that we really had the chance over our winter break to see each other more often which for me was that missing piece that I needed all along. I decided to invite him to my hometown to meet my parents and little brother a couple days after Christmas. We spent an incredible day together and had dinner with my family. That whole day I just kept looking at Jack like, for real, I’m going to marry this man. I don’t know what it was, I can’t even pin point the exact moment or reason, but it was just as if all the stars had finally aligned, the timing was perfect and my love for him fell on me like a ton of bricks. I realized he was the best man I would ever know and I could actually picture myself walking down the aisle with him at the end of it one day and him being the father of my children.
So, before we were even “boyfriend/girlfriend” I did another thing. A kind of big thing. As I walked him out to his car before he left my parent’s house I stopped him in my front yard and told him “I love you” under the stars and two-day old Christmas lights. It was the most magical moment of my life. He was in shock at first because we had waited for this moment for so long and after a few moments of wide-eyed staring at me he said “I love you too”, and the rest is history my friends.
how they asked
It was the end of summer and I had just finished my first clinical rotation for my second year of grad school. I would be moving to Louisville, KY for my second rotation in a couple weeks so Jack was going to take the weekend off to help me move out of my apartment in Lexington and get all of my stuff home. We got home late that Friday evening but I surprisingly woke up at 7 AM (hello internal alarm clock that will never let me sleep in again) the next morning. Jack always sleeps downstairs on the couch at my parent’s house so I went down there to give him a kiss on the forehead/bother him while he tries to sleep before I went on my morning walk. But plot twist!
When I went down there he was nowhere to be found. In his place on the couch was a gorgeous dress and a note that read “Good morning gorgeous! The day is planned & waiting for you. Put this on & be ready at 10:30 (underlined to emphasize that I better actually be ready on time for once)”. So then I found my mom and dad in the kitchen, showed them the note and they preceded to act like they had no idea what was going on. Putting makeup on was a struggle as I kept tearing up from excitement. I knew something really special was going to happen today but I didn’t know then exactly what!
Jack showed up a little after 10:30 and boy did he look handsome. We have never been awkward around each other in our life but this car ride was an exception. I had so many questions that I knew I couldn’t really ask and I just giggled the whole way to our first destination. Our first stop was my favorite coffee shop downtown on the river. We got some coffee and set out on a bench beside the river and enjoyed the rare 75 degree weather in late July. It was the most beautiful morning. I, obviously, knew something was up so I just tried to remain calm and not be too anxious.
After about an hour of nervous talking we walked back to the car. When we got inside he told me he had a gift for me. It was a handkerchief with our initials monogrammed. There was something different about this one, though. When I looked closer it read “J S H”. OH MY GOSH! I freaked. And cried… a lot. That was our initials with what would be OUR last name. Jackson and Holly Sherry. So my suspicion was validated and I was so excited I couldn’t contain myself. I thought okay he’s going to ask now… be he didn’t. Not just yet. He said, “Okay, time to go to our next stop!”. TORTURE. Next stop- a garden. Jack drove me out to a botanical garden just on the outskirts of town where we were the only ones there. It was one of the most romantic things we’d ever done. As we walked around I tried to take in all the sights and stop to smell the roses (no pun intended) but I was so anxiously awaiting a proposal I could hardly stand it! Jack would just say “You wanna go check out the bridge over there?” and I’d nervously respond with, “I don’t know…should we go check out the bridge over there?”.
I was going crazy with excitement and anticipation! He finally could read it on my face and sat me down on a bench where he basically told me to calm it down and held me in his arms. I took a deep breath and decided that the rest of the day I would remain calm and basically get it together. About that time, we spotted an elderly couple and began talking about how that would be us one day and how we’d never stop having fun and holding hands everywhere we went like they were. It was enough to calm me down, for sure. We walked back to the car where he had another gift waiting for me. This one was even better than the last. It was a jewelry box and inside was a bracelet with a charm that read “forever & always 07-29-17.” Once again I cried a lot as he drove me to our next to last destination. We sat outside of a restaurant downtown where we drank some wine, ate great food and talked. We were both so excited and just couldn’t wipe the smiles from our faces.
Afterwards he drove me to the final destination which was a park out in the country off of the backroads. He led me on a trail through the woods that ended with a walk across a swing bridge over a creek and came to a dead end. He then took me to a clearing in the trees that opened up to the most beautiful scene. A field where the sun was shining bright and there was a table set up on a quilt with old pictures of us, baskets of wildflowers and one last gift. THIS WAS IT! The time had finally come and it was more than I ever could have dreamed.
Jack took my hand and brought me over to the table. I started looking at all of our old pictures and when I turned around he was on one knee. I could not stop giggling. I had waited for this moment my whole life and then this whole day and it still felt so surreal and like wow this is REALLY happening. I was giddy beyond belief. When we finally both stopped laughing he grabbed my left hand and as he stroked my ring finger he told me how much he loved me and how he never thought he could have met someone who made him rethink the entire idea of what he thought love was- which he had to repeat to me later in the day because in the moment I blacked out and couldn’t remember anything.
It was the most beautiful moment of my life. He put the most gorgeous ring on my finger and I of course said yes as he literally swept me off my feet and spun me around. We opened the final gift which was a bible and journal, each with handwritten notes from him that I will cherish for a lifetime. Then we walked over to the swing bridge where Jack pulled a lock out of his pocket with “J+H” written on it. We locked it on the bridge, said a little prayer then threw the key into the creek below.
When we got back to car it hit us all over again and we just screamed “We’re engaged!” over and over. It was amazing. We drove back to my parent’s house to give them the big news and when we got there my whole family was there to surprise and celebrate us! We then spent the rest of the night drinking champagne, eating and receiving the sweetest and most valuable advice from the couples in my family. No more tears have ever been shed. I will never be able to to get over just how perfect and out of a fairytale the whole day was. Almost a year ago to that day my dad was diagnosed with Early Onset Alzheimer’s. It’s crazy how the absolute worst year of my life ended with the absolute best day of my life. My dad did not stop crying the whole night and by the end of it I finally got to talk to him one on one. I asked him, “Daddy are you freaking out?” and he responded “No, everything is exactly how it should be,” and I couldn’t agree more.