Kyle and Caroline

How We Met

We met junior year of college during the spring at Lehigh University, we were 21 years old at the time( we’re only 3 days apart). I will always remember the night, it was raining and I was driving down “The Hill” which Caroline’s sorority house was next to my fraternity. Caroline’s sorority had a party with another fraternity and there was a car in front of mine giving rides to the party. Once that car was full, Caroline and her friend started walking to my car assuming I was part of that fraternity giving rides to the party. They tried opening the doors so I unlocked my car and let them in and told them I wasn’t part of that fraternity but couldn’t leave them in the cold and rain but that I was happy to take them to their party.

They had asked if I was going out that night but I played on the lacrosse team and we had a game the next day, Caroline gave me a kiss on the cheek and thanked me for the ride. The next night following our lacrosse game I had reached out to Caroline to see who her sorority had a party with and I reached out to my buddy at that fraternity to help facilitate us hanging out. Since that night I picked her up, I always say she was “The Girl from the Rain.” We started to gradually hang out more and more and practically lived together senior year and following graduation we moved together to New York City and have been together for now over 5+ years.

Marriage Proposal Ideas in Malibu Rocky Oaks Estate Vineyard

How He Asked

It was always my dream to go to Malibu Rocky Oaks, I have seen the estate vineyard previously in the Hangover 3, Entourage and I have followed the property/owner on Instagram. I have never seen a more spectacular property and knew just the setting alone would completely blow Caroline away and make for the most unbelievable pictures that we will have forever.

Weeks of detailed planning went into this proposal across the country, outside of process of creating the perfect ring. After everything was booked and my surprise trip was approaching, I left Caroline with a packing list to wake up to while I was at work on a Friday morning. Caroline had absolutely no clue where we were going but I did tell her we are going away somewhere warm for 7 days and gave her with the weekend to pack, run her errands, and to just get excited for our surprise vacation which we would be leaving for on Tuesday morning.

Tuesday morning as we zipped up our bags and got ready to leave for the airport that’s when I handed her the plane ticket to LAX. Still then she had no clue of where we were staying or what we were doing just that we will be in or around Los Angeles. Once we arrived and got our bags I told Caroline we are going to Santa Monica. Tuesday and Wednesday for me were my days to distract myself from thinking about the upcoming proposal and make final arrangements with my photographer Jillian and the florist who custom made a floral crown and hand bouquet for the big day. These were also days to just relax and enjoy beautiful sunny California with my best friend. I chose to stay in Santa Monica because I wanted to be near the beach but also more importantly for its close proximity to Malibu.

I woke Caroline up Thursday early morning around 5am and told her she should take a shower and that I had a full day of activities planned for us. When she got out of the shower the stylist I had booked from BeGlammed was there to do her hair as well as an order from room service for us. Obviously Caroline asked what all of this was for and what are we doing, I told Caroline we are going to a vineyard and then to Beverly Hills for the day so lets pack several outfits and since we had a car we can bring options and could leave everything in the rental car. I also said to bring everything she might possibly need since we would be leaving the hotel for the day.

When Caroline was ready I got the car and we started driving along the Pacific Coast Highway towards Malibu. Malibu Rocky Oaks is a gated estate so while speaking with the property in the weeks leading up to the big day we were on the same page for when I had to ring the bell at the gates and I said Caroline and Kyle are here for the vineyard tour without giving away the big surprise. When we drove up the winding roads of the vineyard estate and you could see the incredible property at the top of the mountain it was truly just like a dream.

When we got to the house and parked, a woman from the estate came out and said to us just follow these steps down and the guided tour will begin. I took Caroline’s hand and we walked down the steps with wine barrels on the sides that led towards a helipad. In the center of the helipad was the floral crown and hand bouquet that I had ordered and that my photographer Jillian had brought and set up prior to our arrival. When Caroline saw the floral crown and bouquet and realized there was no one else but us at the property I believe thats when it truly sunk in and she realized what soon will be happening.

Kyle's Proposal in Malibu Rocky Oaks Estate Vineyard

On that helipad on a cliff overlooking all of Malibu with nothing but a few clouds in the sky, with the ocean in the distance, and the most beautiful setting I could ever imagine, that’s where I held Caroline’s hands and spoke from the heart and then got down on one knee and asked my college sweetheart to marry me.

Engagement Proposal Ideas in Malibu Rocky Oaks Estate Vineyard

Afterwards, thats when 2 photographers who were hiding along the vineyard to capture the moment came out and gave us hugs and we started our photoshoot all around this truly magical place that is Malibu Rocky Oaks. Following the photoshoot one more surprise was having lunch at a table along the ocean at Nobu Malibu. August 3, 2017 was a day from a dream. A dream come true.

Kyle and Caroline's Engagement in Malibu Rocky Oaks Estate Vineyard

Special Thanks

Jillian Rose
Photographer
Lisa Anderson
Photographer
TheCrownCollective
Created custom floral crown and hand bouquet