Jan and Vladimir

Jan's Proposal in Maui, Hawaii

How We Met

Jan and I met over a dating app called, ‘Happn’. The app indicated that we have crossed paths somewhere in downtown Toronto. We both mutually swiped right on each other’s profile – and that’s when the match-made-in-heaven happened! I messaged her first, and right from the get-go, our interaction was fun and refreshing. From our initial conversations, I can already tell there was a great vibe about this woman. She knows how to carry a great conversation, and she was genuinely interested in learning about me. We got along well and really clicked. We share numerous common interests, including Our love for food, traveling, adventures, and TV/Movies. The more we chatted, the more intrigued I was to know and meet her – so I eventually asked her out to go on a date.

Jan and Vladimir's Engagement in Maui, Hawaii

I was already drawn to her, based on her on the photos on her profile — but seeing her in person was awesome. It was incredible to finally meet each other, and finally, put a face to this woman I’ve been having great conversations with behind the phone! The first date went really well, as we got to know each other over drinks. A second date happened not too long after, and we came across the fact that she had previously dated someone I went to High School with. It was pretty crazy because I would hear about her from this acquaintance (and she had heard about me also), but never met in person. We went on more dates and hung out more, and I knew I was really into her. We took our time getting to know each other and ensured that we weren’t into rushing into a relationship. As days and months passed, I became more and more intrigued by Jan. We are both passionate about traveling, so it was important for both of us to date someone who is compatible to travel with. This important test came a few months into our relationship, as we decided that instead of getting each other pricey Christmas gifts, we should instead — go on a vacation. We went to the Bahamas and enjoyed the beach and sun. We both had an amazing time and realized that we both enjoy each other’s company. We both passed the test, and also knew we were falling in love with each other.

Fast-forward to the Spring of 2017: I had a taken a few days off of work to take care of Jan after she completed a medical procedure. During this time, I was able to do everything that a boyfriend should do when his girlfriend is on the mend and assisted her whenever possible. Jan recognized my efforts and was touched by my sincere care. This was a turning point for Jan because it led her to say that I was “the one” for her. I really appreciated her revealing this to me, and also validated the fact I knew she was “the one” for me as well. By this point, I came to a realization that she’s my best friend, my confidant, and The One.

Where to Propose in Maui, Hawaii

How He Asked

Our first vacation together went extremely well and memorable, so it wasn’t long after that we started planning our next vacation to create an even more memorable trip. I mentioned Hawaii, because she’s a beach bum, and it was on her travel list. Having previously gone to Oahu before (and wanting to go back) – coupled with her not having been before – made it an easy choice. We planned to do Maui and Oahu, and we booked our vacation for August 2017! I always knew that I wanted to propose to Jan in a romantic setting during a vacation, and Maui fit the criteria. It was scenic, romantic, and not overly crowded.

I thought long and hard on how I wanted to surprise Jan. I wanted to make the proposal extra-special, romantic, and memorable. Jan had always joked around how she wanted a professional photographer to take photos of us while on vacation as a keepsake. My first step was in creating this proposal was to find a photographer, and I came across Rodrigo’s work. His portfolio and shooting style was something I really loved, and made it a great match. I reached out to Rodrigo Moraes (of Rodrigo Moraes Photography in Lahaina, Hawaii) about how I envisioned my proposal to Jan, and what landscape and scenery I had wanted. We both bounced-off ideas, and worked together to capture what would be a big milestone in mine and Jan’s relationship.

I wanted to propose to Jan early in the vacation. On August 11, 2017, I had planned for us to spend our second vacation day as a beach day, and spend the late afternoon exploring/shooting photos at a Maui plantation. While in Napili Beach, Jan became curious about our afternoon plans, because I kept changing my mind when to leave the beach to be ready for our “excursion”. In actuality, I was coordinating the time to meet with Rodrigo to catch the right time for the sunset. So Jan, the beach bum that she is, wanted to stay longer, and would rather sacrifice preparation time for more beach time. I eventually gave in and told her that we had a pending photo shoot with a photographer I saw on Instagram, and to look “photo-ready” — which made her agreeable to leave the beach early. I was a couple of hours from proposing to the love of my life, and I was already shaking due to nerves. Jan had noticed I was really quiet and acting strange also. I played it off as if it was nothing, and drove back to the hotel to get ready. We met with Rodrigo, and he took us to the site in north-west Maui. Jan and I were amazed at the scenery. We were standing on a cliff overlooking the ocean and admiring the beautiful landscape of rocks and rolling hills. Rodrigo encouraged us to go explore the area — which was the cue for me to go do my thing. I found and settled on a perfect spot with the ocean as the background. As Jan was admiring the scenery, I pulled her towards me and told her how much she means to me. I told her the speech that I had prepared for her, emphasizing my love for her and how much she makes me happy. I got down on one knee and asked her the most important question I’ve ever asked anyone.

Her reaction was priceless, filled with genuine surprise — along with so much joy. She said ‘yes’ — to spending the rest of our lives together!!! Jan was speechless, and was overwhelmed with so many emotions and was so surprised that she didn’t even remember that I got down on one knee – or that she even said ‘yes’ to me. Rodrigo captured our special moment, and then we also proceeded to have our Engagement photo shoot in the beautiful landscapes of North-West Maui.

I had planned a romantic dinner at the famous Mama’s Fish House that evening to celebrate our engagement. We spent the rest of our Hawaiian vacation just enjoying the beautiful surroundings of Maui and Oahu as a newly engaged couple.

Special Thanks