Blog, Destinations

Santorini Proposal

WE ARE FINALLY ENGAGED!!!


Since we’ve already been asked a million questions, and unfortunately haven’t had the time to call all of our loved ones yet… I figured I would capitalize on this ferry ride to Mykonos to share my story and how this came to be.

For those of you that know me, I like to have a plan. Complete opposite of Jacke, but clearly opposites attract 🙂 I’ve been planning this day for about a half of a year now, but it has changed over a 100 times in the meantime. I’ve had so many internal battles on where to pop the question, what to say, what ring would she like, how do I ask her family, how to keep everyone involved, how to pick the perfect photographer, etc.

I’ll start from the beginning and talk about my first conversation with my Mother. She knew my obsession for travel was never going to go away, but eventually it came to “What do you think about me quitting my job to travel the world?”, where her first response was “What about Jacke?!” not what about my job, how to do it, where am I going, but her first concern was about Jacke being a part of this. I think that shows how much my mom truly adores Jacke and how she is already a part of our family before we even get married. “I’m going to bring her with me!” “So you expect Jacke to quit her job, leave her life and family behind, and to travel the world with you without a ring or commitment?”, when I replied, “I’m going to ask her to marry me on the trip!” and after a few cheers of joy, you could say the rest is history!

Next was asking the Blackwell’s. My only regret throughout this process is not asking for permission sooner. I intended on driving down to ask Jeff for his blessing, but wanted to wait until after Christina and Logan (Jacke’s brother) wedding was over in April. I didn’t want to take away from the excitement of his son’s wedding, so I intended on doing so after Logan had an opportunity to share his big day with his Father. Unfortunately with Jeff’s unexpected passing, we didn’t get to experience this moment together. I didn’t get to spend as much time getting to  know Jeff as I would have liked, but it would have been an honor to ask for his permission to have Jacke be my wife, the mother of my children, and my best friend for the rest of my life. I hope he is watching from above and enjoying front row seats to our journey around the world and engagement. He’s passed so many amazing traits and qualities on to his children that it’s impossible not to think about him when around his two most prized possessions. Jeff thought the world of Jacke, and I promise to do everything I can to give it to her… and now I have tears running down my face on a ferry surrounded by strangers as Jacke sleeps next to me. I’m kind of an emotional person if you haven’t noticed yet.

In Jeff’s absence, next was to ask the love of his life. My girl Terri!!! Didn’t really know when to ask her, so kind of just popped the question outside of her hair salon one day. “AHHHHHHHH ARE YOU SERIOUS?” or at least I think thats what she said, but my ears were ringing so badly from the scream that I’m still not sure to this day if thats what she actually said. So we hugged and cried, and then she came over later to help customize a ring online… but we scratched that idea later.

Logan… a man of few words, but always the best ones. The only other person in this world other than Jeff that I’ve never heard a person say a bad word about. I assumed he would be cool with it, but I’m pretty sure he wanted to kill Jacke when he found out she was starting to date me because of my party days in high school and college. One night we were all hanging out over at Logan and Christina’s house when the girls wanted to go for a walk with the dogs. I almost went, but then last second canceled because this was the one free moment I had to ask. Logan had no desire whatsoever to go on the walk because hockey was on. So I don’t know if he actually said yes to my question, or because a goal was just scored and he was excited! Either way, I’ll take it and I’ll never forget the smile on his face when I asked for his permission to marry Jacke. Hey Logan…. Whats up BROOOO!!! too early? Hate me yet? 🙂

Next was picking out a ring. This is where Terri and Christina stepped in to save the day! I think we all had a rough idea what she would like, but we headed to Distinctive Diamond to pick the perfect ring for the perfect girl. All the hours of research I had done trying to teach myself about these clear rocks called Diamonds (4 Cs!!!! I dare someone to quiz me on diamonds), her Pinterest, and listening to her and her friends talk about heir their rings, it went out the window for the most part. We eventually decided on a cushion cut with a simple diamond band since she likes simplistic and timeless styles. Since I’ve now had to hear her say “It’s the most beautiful thing I’ve ever seen,” and “It’s so perfect!” 100 plus times a day… I think we did a good job ladies!

After all of this, I still had to pick when and where. Since we were fully committed to this trip at this point… it was my dream to do it on our World Tour. We both knew early in our relationship that we would be life partners, and I had always dreamed of proposing in one of the most beautiful places in the world. When we first started talking, I asked, “If you could go anywhere in the world, where would it be?” when she shouted “Santorini!!!” (I’ll probably be deaf by the time I’m 40 being around Jacke and her mom). She named a few other spots around the world, with Paris being another. So I was torn between Paris and Santorini, but Paris was too predictable. Additionally, I started to second guess myself as I didn’t want to leave everyone out of this… so I almost did it before our trip! I was a few days away from trying to plan a “going away party” that would be turned into a proposal for everyone to enjoy/celebrate. My heart kept telling me otherwise, and I followed my dream of asking her in Greece.

Anyone that knows Jacke knows that she likes pictures. Not just a few pictures, but like thousands and thousands…. For example, if we go on a long weekend getaway, expect to take approximately 500 pictures, make me take 50 selfies (she likes 1 out of every 200 on average), and document every single thing we do. In the moment its annoying, but I always appreciate it later on. I knew a photographer was a must. I could probably tell you every photographers name in Santorini by now, but I found the perfect one (Eva Rendl is the best!)! We shared the same vision and she knew exactly what she was doing. Her pictures on her website were some of the best I had ever seen, and I was lucky enough to secure her for August 30th for sunset! We sent pictures, locations, and ideas back and forth for weeks until we found an ideal setting. Now, I just had to wait.

Everyone keeps wondering how I kept the ring hidden for two months. Surprise! I didn’t! my parents had purchased a Greece vacation package a while back, and it was the perfect opportunity for them to visit us while in Europe! So to avoid having something happen to the ring or her find it, I kindly asked them to bring it along with them. I planned dinner reservations for a sunset view over the Santorini Caldera, but had them inform Jacke that dinner was an hour before scheduled. Since we are backpacking, we really didn’t have much for clothes. So I had my mom ask Jacke if she had anything decent to wear out to a nicer restaurant for while they were in town. She didn’t have many options, so Jacke asked her mom to send her something. The plan was set, now all that was left was to execute it!

The big day is finally here! We spent all day exploring Santorini on the ATVs, and I was trying to do anything to keep my mind off of it as I was getting a little nervous. As the time approached, we headed to a Mexican restaurant for some margaritas to lighten the nerves and enjoy ourselves. It was time to head back and get ready for the the big moment! After months of planning, I wanted EVERYTHING to be perfect…. this never happens when Jacke is involved. We are already a little behind on getting to our place and then I hear “WHATS THIS STRAP FOR?” *rips strap* and there goes the perfect dress her mom and Christina picked out. I’m trying not to panic on the outside, but I’m freakingggg out on the inside as she doesn’t have anything else to wear. I ask the front desk for a safety pin and they have nothing. We cant find anything, but as if a sign from God… her mom sent two dresses and the other dress had a safety pin attached to the tag! What are the odds!? So I safety pin her dress strap back on so her dress doesn’t fall off her. Running a little behind, we head to town.

I’m pretending to find the restaurant that we are going to for “dinner.” What I’m actually doing is trying not to have a heart attack while finding the church we are supposed to be at now. Being such a photogenic spot, I see some people standing right where I’m supposed to be proposing. So I stall a little with taking pictures, but I see Jacke has her eyes on the prize. It was the light at the end of the tunnel and she wanted to take a picture there. The photographer is sitting there pretending to be a tourist and acting the part (everyone has a camera so she blended right in), but I still had to wait on the other couple that was already there to move. I panic, “Lets take a selfie!” as that was the first time in my life I’ve ever said that. “Really?! So nice! yea!!!” worked like a charm as we take a few selfies while I try to hide my temporary Parkinson’s disease. The couple eventually moved and Jacke turned around to admire the church next to us. This gave me just enough time to pull the ring out of my pocket and get on one knee to ask the famous words, “will you marry me?”. The photographer captured this perfectly as Jacke covers her mouth and tears start pouring down her face.  “AHHH ARE YOU SERIOUS?!” came out of her mouth, just as it did when I asked her mother for permission (twins!). We spent the next 5 minutes shedding tears of joy together, and having the streets of Fira, Santorini filled with cheers of joy and celebration. We then walked around of the town of Fira for the next hour kissing, laughing, crying, celebrating, and enjoying our time while the photographer captured what will be the best day of our young lives. After it is all said and done, this day was the perfect day with the perfect person.

We then celebrated over champagne, dinner, and wine… and more wine… and more. Until the hours of celebration came to an end and it was finally time to head home. She will hate me for sharing this, but I feel obligated to share the full story! Jacke can never admit when she’s had too much to drink… She never gets drunk, but when she does, she denies that she is. As we get up from our table to leave I notice she’s a little wobbly. Very first table she passes she bumps into their table, and by the time I’m done saying sorry to them, she’s almost fallen into another man’s lap at the next table before she eventually finds the stairs… oh boy. She’s holding on to the railing with two hands when for the first time ever I hear “I’m actually drunk.” Time to walk home with her and my mother in the exact same condition when we finally arrive back to the hotel. Somehow my mom’s shoe has fallen off. So now I’m trying to help her put her shoe back on, while Jacke is holding on to my arm for dear life (I have the scratch marks to prove it)… I look up and see some family horrified, but I just smiled back because this is my new family and I couldn’t be happier!

Takeaways from Santorini:

  1. Marry your best friend!
  2. Love like there is no tomorrow.
  3. Put a limit on girls celebratory wine glass count.
  4. You can ask where a girl wants to go, but never ask why. As when my mom asked Jacke after the engagement, “How did you know you’ve always wanted to see Santorini in the first place?” I had to hear the terrifying words, “because I saw it on the Kardashians!” *immediately regrets everything*

Bonus post:

For anyone still reading, I just wanted to give a big shoutout to all of those that made this possible. I want to thank Terri and Jeff for raising the most amazing person in the world and the love of my life. Also, Terri and Christina for helping me find the perfect ring, plan, pick out a beautiful dress, and countless other small things that helped bring together the perfect moment. Thank you Logan for not killing Jacke over the years of her annoying you, and giving me permission to take her off your hands. Thank you to my Mom, Sister, and David for supporting my crazy decision, pushing me to take chances, and welcoming my fiancé with open arms into the family. An extra thank you to my mom for helping me from start to finish on how to make this such a magical moment for the both of us. A big shoutout to all of our family members and friends who told us to take a big leap of faith and go on an adventure of a lifetime. We wouldn’t be here today without you, and we love you all!

12 thoughts on “Santorini Proposal

  1. This is beautifully written and truly captures the joy and love of that special day. Thanks so much for sharing! Love you both SO much! ❤️

  2. This is the sweetest thing in the world, so very happy for the best couple! Your story is precious, and I cannot wait to follow the rest of your incredible trip together!

  3. Absolutely amazing, I knew you would make it a perfect memory making moment in time! Welcome to this crazy, loud family Damian! You and my husband will get along perfectly one day…I just know it!

  4. Love reading about your dreams as they continue to unfold and become part of the lives you will share together forever! Love you both! ❤️

  5. We love you and enjoyed sharing your special day.

    Jacke is a lot like your Mother in many ways. They pass out when they drink too much and I have a feeling we will be spending more “quiet time” together.

    We are thrilled to have Jacke as part of the family.

    Love you two!

  6. Well said, son ( I may be shedding a tear or two). We were blessed, delighted, and honored to share your moment! I’m so proud of the man you’ve become.. Jacke is a lucky girl. And Jacke you’re pretty darn perfect… after all, we often strike the same pose after over celebrating !! ( thanks for not posting those photos son!!!)

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