How We Met (her perspective): Ryan and I both attended the same university, but I transferred out before he and I met. However, he and I had some mutual friends and we began to see one another through them.
I started really liking this cute, fun guy! So I asked our mutual friend if she thought he might be interested. One day we planned to go to a movie together. Through the whole night I tried to look for clues if it was a “date” or not. It remained a mystery! But we continued hanging out and finally, the day before my undergraduate graduation, I asked him clumsily, “So, are we boyfriend and girlfriend, or what?” He said yes, so I guess that’s where it began! We still consider that movie night (Pan’s Labyrinth) our first date: March 6, 2007.
Since then, we’ve lived in Connecticut, then 2.5 hours away from each other in Connecticut and New Hampshire, and then finally moved into an apartment together in Massachusetts. Fast forward a couple years — we just recently bought our first house together and couldn’t be happier. Now our attention has turned to planning the wedding!
How I asked (his perspective): Want to know a great test of a relationship? Share a canoe together.
Since 2008, I had been going with Kait on her family’s annual canoe trip. We had talked about getting married before, and she had even been known to playfully jab at me about getting down on one knee. In the early spring of 2012, I decided to jump into proposal-mode with both feet, and my mind was made up that our five-year anniversary would not pass without Kait having a ring to show for it.
Finding my perfect idea came easier than I thought. I had struck up a conversation with the owner of a canoe & kayak rental business near my office building, and mentioned how Kait and I loved being on the water and that I was thinking about proposing soon. He said that there was a small park overlooking the Zakim Bridge that might be a perfect setting if we were willing to paddle a little ways. He also gave me the number of a photographer friend of his, just in case I was interested.
The photographer and I hit it off right away (she was an avid paddler) and I came up with a plan: I would paddle out to the park with Kait, and propose at the crest of a hill overlooking the Charles. The catch: the photographer would pose as a tourist and capture the candid moment from a safe distance. She even paddled out with me for a test run. We kayaked to the park, found the perfect spot from both my perspective and the camera’s, and worked out the finer details of the plan.
A few weeks go by, and Kait passes a major test for professional licensure. I told her: “Hey, I’m taking you out for lunch in Boston to celebrate!” She agreed and we were off. After a delicious lunch, we walked over to the canoe & kayak rental. The weather was perfect, but the lines were long. I had coordinated with the photographer to be at the park at a certain time, and now I was getting nervous about having her wait forever before we even showed up, let alone propose.
The line wasn’t budging, though it seemed to me that everyone only wanted to take out kayaks and not canoes. According to a posting on the wall, canoes wouldn’t be rented out if the winds were at a certain strength, and this wind was toeing the line. Luckily, having spoken with the owner beforehand, he knew about my plan and who I was. So when Kait and I went up to inquire about taking out a canoe, an exception was made and somehow we got bumped to the front of the line with canoe paddles in hand. He had to act like he had never met me before, and he acted the part perfectly.
I had a ring in my backpack, and I was padding with Kait on the Charles River on a gorgeous May afternoon. She looked beautiful. I managed to convince her that we should navigate through a narrow boatway, telling her that ‘I had heard about a nice park’ over on the other side. She thought we weren’t supposed to take the canoes out that far. That hesitation continued when we pulled up to the park and I wanted to dock the canoe and walk up the hill a short ways. My photographer-posing-as-a-
I worked up the nerve and took her by the hand up the hill to the secretly-agreed-upon-spot. I got nervous and weird as I worked back through everything I wanted to say in my head one last time. I wanted Kait to remember this moment for the rest of our lives. She could see that I was being weird. But it didn’t matter when I pulled the ring box out of my backpack and got down on one knee. I said exactly what I wanted to say, and she gave the answer I wanted to hear. It was an amazing moment.
The next moments were a lot of fun. We were hugging and kissing, and then I turned her attention to the woman who was no longer reading a book. I said “…and see that lady over there? That’s our photographer! She just captured the whole thing!” I love surprising people, and Kait was truly surprised and shocked and amazed. If she had figured out that I was about to propose being awkward on the hill, this made up for it.
We went over and talked and laughed, and met a couple with their dog who seemed just as excited as us. They were clued in on the plan by our photographer and got to watch the whole scene play out. I had booked a photo session, so Kait and I got to take more pictures together around the park with the new shiny addition to her ring finger.
Everything had gone off without a hitch. The weather could have been lousy, the canoe rental could have gone south, we could have somehow flipped our canoe, there could have been tourists overcrowding the proposal spot. I had to secretly pack Kait a change of clothes because I was now bringing her to Connecticut for a surprise party with both our families waiting (she started looking for a shirt that I had packed at one point, leaving me sweating bullets). But everything worked out.
Kait and I have passed the ‘canoe test’ for the past five years and counting. We’re getting married in January. And we just booked our campsite for this year’s family canoe trip.
Photos by Bethany & Dan Photography
How I Asked: Lindsey’s friend Karlee told Lindsey she wanted to take one last girl’s trip together before she would get married. Karlee loved the idea and said she wanted it to be something really special. Later that week, Karlee called to say she went ahead and …