Real Proposal Story: A Boston Engagement on the Charles River


First comes love, then comes marriage. But before the joy of wedding planning begins comes the biggest, happiest question of all: Will you marry me? Thanks to HowHeAsked, we found some real, romantic, and ridiculously creative proposal stories that will get you inspired, tearing up, or both!

It's no secret that love requires taking a risk. For Kaitlin and Ryan, a romantic relationship hinged on one gutsy question: "So, are we boyfriend and girlfriend, or what?"

The couple should have met long before they actually did, considering that they went to at the same college, but Kaitlin transferred before they had a chance to meet. When they finally did, they became fast friends and started going out on dates—but neither of them called them that.

See more: Design Your Dream Engagement Ring

It wasn't until the day before Kaitlin's college graduation, when the pair were at a movie, that she got up the nerve to ask Ryan the "are we official?" question. He said yes, and that night, March 6, 2007, marked their "official" first date.

Fast forward to 2012, just in time for the couple's 5-year anniversary, and Ryan had proposal plans on his mind. This time, it was his turn to take the risk! For years, Ryan had been joining Kaitlin's family's on their annual canoe trip, and a chance conversation with the owner of a canoe and kayak rental business near his office building sparked his plan...

Hearing how much Kaitlin and Ryan liked boating, the owner mentioned that there was a small park overlooking Boston's iconic Zakim Bridge that would be a perfect setting for a proposal—if they were willing to paddle a little ways. He also gave Ryan the number of a photographer friend of his. A perfect proposal was coming together.

Ryan and the photographer, an avid paddler herself, came up with a plan: Kaitlin and Ryan would paddle to the island, where he would propose at the crest of a hill overlooking the Charles River. The photographer would pose as a tourist and capture the candid moment from a safe distance.

The perfect time to pop the question after Kaitlin passed a major test for professional licensure. Ryan said, "Hey, I'm taking you out for lunch in Boston to celebrate!" He knew the lunch would include canoeing and his own gutsy question.

See more: Over-the-Top Places to Get Engaged

The line to rent canoes that was long that day, and the winds were almost too strong for boating. Luckily, Ryan and the photographer had made a proposal test run beforehand, so the owner made an exception for them. "He had to act like he had never met me before, and he acted the part perfectly," Ryan fondly recalls.

As they rowed, Ryan told his future fiancée about the nice park he wanted to canoe to, but the distance made her pause. Still, they made it over to the spot, and the scene was set.

Ryan cops to being so nervous that he worried Kaitlin could tell something was up. But once he got up his nerves, everything went smoothly. "I said exactly what I wanted to say, and she gave the answer I wanted to hear," he says. "It was an amazing moment."

Our Takeaways

1. The power of a trial run: If Ryan and the photographer hadn't done a practice run, they wouldn't have known the perfect proposal spot, and they might not have gotten there in the first place! It just goes to show that even with marriage proposals, planning and practice count.

2. Nerves are normal: Ryan mentions how nervous he was—at one point Kaitlin almost found the ring!—but he still managed to keep calm. He had an elaborate day planned, and things almost went wrong, but he got the prize in the end!

3. The meaning behind it all: The activity that binds Ryan to Kaitlin's family is the one he chose to use for a proposal, and to wonderful effect. "Kait and I have passed the 'canoe test' for the past five years and counting," Ryan says. "We're getting married in January. And we just booked our campsite for this year's family canoe trip."

Click here to read more about Kaitlin and Ryan's engagement and don't forget to follow @HowHeAsked on Twitter!

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