It was early fall of 2014 when I had a sudden burst of inspiration. I knew I wanted to buy Holly an engagement ring. It was a gut feeling. It was something on my mind since the start of our relationship. Throughout our years together I have picked up pieces of what Holly likes in an engagement ring. So naturally, I sifted through the stockpile of memories that had things she said stored in them. I went straight to the mall and looked for hours. I went to a popular jewelry store and didn’t find what I wanted. Somebody in the store asked me “How much are you willing to spend?” and I said “When I find the ring, then I’ll answer that question and I haven’t found it here.” Money wasn’t an issue in the deciding process. So I moved on. I went to another store and this one had a much more vast collection. There were so many types of the kind I was looking for. Finally I narrowed it down. I found the ring. Needless to say, it came home with me. I talked to her parents and presented the ring to them. Lucky for me, I’m very close with her family so they gave me their blessings. Now it was time for the actual planning of how I was going to do it.
I went as far as talking to Holly’s boss from work to get her these specific days off. December 3rd and 4th. I told her to make up some reason why she would need to switch her normal days off. Throughout the years my plan morphed into what it ended up being. My original plan was to take winter photography of her because I have been telling her I wanted to get some new pictures. She agreed to this a month before my target date. I planned on taking pictures of her in the woods, then offering I get into the pictures by leaving my camera set up on a tripod and hitting the timer. Then I’d go to the camera to adjust the angle and hit the record button. I figured I could take as many stills as I want from the recording on my 60D camera. After hitting record, I’d talk to her a bit and then get down one knee. I didn’t want her to suspect a thing. I wanted to do it in front of this cottage in the Santa Cruz mountains. The plan was set. The only thing missing was the ring box.
In early November, I had this idea because the ring box given with my purchase wasn’t doing it for me. Remember in the movie “Up” where Carl sees what Ellie wrote at the end of their adventure book? Ellie was basically saying that being with Carl was the adventure all along. Not all the things she said she was going to do. She didn’t fail by not doing these things. She had Carl the whole time. Holly and I have always loved the connection Carl and Ellie had. So it was only appropriate I get her a ring box that was a replication of the Adventure book itself. It fits in the palm of your hand and at a glance looks like a replicated little book and nothing more. Then when you open it up there is a page that reads “You and me, we’re in a club now.” Then behind the page is a soft cushion holding a ring with a ribbon. It shipped from Canada after I purchased it at the start of November and didn’t arrive until about 3 days before I purposed. I was so relieved. I felt like I dodged a bullet and everything would go smoothly.
But as fate would have it, due to all of California complaining of the drought, mother nature decided to shut us all up with a steady downfall of pouring rain. Why was this such a problem you ask? Well, I told Holly not to plan anything on this day. She didn’t. But then she asked what we were doing. I told her it was a surprise but I’d tell her the night before so she could be prepared. I told her the night before that we were going to have a photoshoot in the woods near this awesome cottage and she talked about how it was raining, but we should do it another week. She felt bad but I felt WAY worse than her. She had no idea that this was my bait to get her out there. I was stuck. I didn’t know what to do. So I decided at the end of the night I was going to make up a story about me getting into a fight with my dad so she’d want to cheer me up and we’d go to lunch in Capitola. Which is about 20 minutes from the location I wanted to take her to. Naturally, being the amazing girl she is, she was totally down for doing whatever I wanted to help cheer me up. Even while it rained throughout the bay area. She knew we were about to drive through the rain through the Santa Cruz mountains and still didn’t hesitate to join me.
So now we are driving to our destination. The whole way there we were just talking and laughing about silly things we were seeing while driving. Example: Holly loves watching planes take off so we watched this plane climbing from the San Jose airport into the clouds and she said “There is an opening in the clouds! Go through the opening!” And I said “OH MY GOD! HE’S GOING RIGHT FOR THE CLOUDS! WHAT AN IDIOT!” We made the pilot seem like a moron for not trying to aim for the break in the clouds. This was hilarious. We couldn’t stop laughing. Fast forward about an hour and 15 minutes. We were driving through a very tree filled area in a forest and she kept saying “Are you SURE there is a restaurant over here?” I kept on saying yes but she grew more and more suspicious when we got onto a one lane dirt road with potholes and muddy water. I drove through this gate that led into somebody’s drive way. We passed a big house on this driveway and then I then parked my car in muddy grass. The owner of this house and cottage was named Mary Jane. The lady who helped facilitate this cottage rental. Anyways, I told her that we should get out and walk a bit and to just trust me. I said “Close your eyes! I have to get something.” I got my camera from my trunk which was completely ready to go. I told her to hold my hand as we went down this steep driveway that broke away from the original big house we passed. Then we stopped parallel to an awesome cottage. So here we are, deep in the woods and all the sudden she’s standing in front of a huge clearing overlooking all the Santa Cruz woods as far as the eye could see. Keep in mind it was super cloudy, foggy, and misty. I set up my camera as she was looking away and I made my approach. I was so nervous. I have spoken in front of 300+ person crowds and performed magic for literally thousands upon thousands of people. But here I was in the middle of the Santa Cruz mountains with one girl in front of me and I was literally shaking. I then told her how much I loved her and how I “want to make her the happiest girl in the whole wide world. I always want to be with you.” I poured out my heart. At this point I think she knew what was coming.
I pulled out the book/box and said “This book represents everything we’ve been through and all of our adventures.” I planned for way more awesome things to say but this is all I could really get around to. My mind was a sea of rough waters. I then got down on one knee and opened up the box. The time was exactly 4:10 pm on December 3rd which was exactly 3 years after the first time I told her I loved her. The rain had stopped just long enough for this moment to take place. My heart started beating extremely fast. I hadn’t eaten all day due to the anticipation. I felt as if I was no longer in control of what words came out. I was completely at the mercy of the moment at hand. I took a big deep breath and said “Holly. Nicole. Caldwell… will you marry me?” While covering her mouth due to the cold, she shook her head up and down and said “Yes. Yes.” She started crying as soon as my knee hit the ground. I got up and gave her a hug and a kiss. As I was putting the ring on her finger, her hand was shaking and so was mine. While putting the ring on her finger she said “Oh my god.” Right after that I said to her “By the way, we’re staying at this cottage tonight.” As I pointed behind her. With eyes full of tears she asked “What about my clothes?” so I said with a smile “I bought you new clothes that are in your duffel bag in my trunk. I also brought food, wine, candles, music, board games, Jenga, and other overnight things.” I asked her if she liked the ring and with a cute tear induced chuckle she said, “I can’t see it yet.” She then asked me “Does anyone know?” so I said “Pretty much everyone. I already talked to your parents and they said yes.” She then hugged and kissed me again because her parents are very important to her so this meant a lot. As we hugged and just proccessed what had happened nothing else mattered in the world. So we went into the cottage, listened to music all day/night, ate clam chowder, beef jerky, and mac and cheese. Not the most romantic of dinners but it fit the atmosphere. During my proposal, the rain turned to just mist. When we got into the cottage it started pouring down once again. It was all perfect timing.
After our initial wave of texts from close friends and family we left our phones alone and just completely enjoyed the moment. We wrote in a journal that belongs to the cottage. People have been writing in it for years now. We read a bunch of really interesting entries. A band who wrote an entire album there, people on anniversaries, sisters reuniting with each other, you name it. What I found interesting was the quote on the cover of the journal. “There are still a few remnants of magic left in this world” The journal was full so Holly and I started our own journal for others to write in. Mary Jane had left it for us to start. We will be back sometime in the future to visit our new getaway. This was the best day of my life and things are only getting better. I hope you enjoyed my crazy tale. And a word to all the gentlemen reading this, I know this was a lot of work but it was so worth it. To give the person you love most, a story to remember for the rest of their lives. Memories like these don’t happen to very many girls. We only go around once, why not create a story so amazing that it surpasses your lives. If everything in this world vanished someday, let love be the thing that remains. Let love be human’s try at creating infinity. In the end, our money, our status, our friends, our YouTube view counts are merely blips on the radar compared to love. Nothing can replace the feeling you get in moments such as these. Give your girl the story she deserves. That’s what life is all about, creating memories that when thought of can only make you happy. No blog post could ever properly describe what you feel during these pivotal life changing moments. Which is why I think I’ll end it here. Thank you for sticking around and reading my story.
Holly’s Fiancé and future husband,