The Proposal

We had been dating less than a year when I proposed, but I already knew early on that I wanted to spend the rest of my life with Helen.

The Ring

Knowing what kind of ring she'd like was actually the easy part. I'm positive Helen doesn't remember telling me this, but I already knew what she liked during our fourth date. I don't know exactly how it came up, but she mentioned liking solitaires on a 6 point setting with a thin band at some point during our conversation. I was already head over heels for her, and I remember putting that exact description into my phone for future reference because I had a gut feeling already that she was the one.

When it came down to actually finding a ring, I was living out of my car on away rotations moving from NY, to PA, to IL at the time, making it a bit of a challenge to find a jeweler that I could work with. Thankfully, my parents knew a jeweler in Toronto who was able to help (thanks mom and dad). I spent hours researching rings and diamonds so I could give him the exact specifications that I wanted. After weeks of back and forth trying to find exactly what I wanted, we finally found it.

The Proposal

For months I actually wrestled with when, how, and where I was going to propose. I had several ideas and options to go on. I thought of doing a scavenger hunt in Toledo going through all of our first dates and memorable locations, a romantic proposal in Chicago across the skyline, and during Thanksgiving with Helen's family, but decided against none of these in the end. September 23, 2018. Helen and I didn't realize this until later, but this date was exactly one year from the day that we first talked to each other. I decided to propose on September 23rd because Helen and I were visiting her parents in Rochester that weekend and my parents were making a trip down for a barbecue. In the end, I felt that our engagement would feel more meaningful with the support of both of our parents beside us.

Interestingly, the proposal might not have happened due to some miscommunication. My parents didn't know I was going to propose that day and almost didn't bring the ring. I hadn't seen the ring in person yet, and I thought I expressed to my parents that I wanted them to bring it, but since they knew I was coming back home to Canada that same evening, they thought I'd pick up the ring back home. The night before, I messaged my mom asking if she was going to bring the ring. She said was confused by my message, but decided to bring it anyway. Crisis averted.

When my parents came in, one of the first things my mom did was give me the ring when Helen wasn't looking. I hadn't seen the ring in person yet, so I quickly went to the bathroom and took a quick peek. It was perfect. I hid it underneath the sink and went back and pretended as if nothing happened. Throughout the entire day, I was incredibly nervous thinking of how exactly and when I was going to propose. It was the only thing I could think of. Every second I kept evaluating whether or not now would be a good time. Since my parents were visiting from Waterloo, they had to make a fairly early drive back to take care of our dogs, Milo and Mika. Around 3PM, my dad said they should probably get going, and it was at this point I went into a state of panic. I knew that if I was going to propose today, it was either now or never. I quickly said I had to go to the bathroom and went to go get the ring. There was only one problem. The ring box was too big to put into my pocket without being exceedingly obvious. Front pocket, back pocket, pant leg. Nothing worked. I spent at least 5 minutes in the bathroom trying to figure out the best way to conceal the ring inconspicuously. I was worried I was taking too long so I just brought the ring down and hid it in the study room and tried to pretend as if I wasn't internally imploding. Thank goodness a few minutes after I got back, Helen decided to go to the bathroom as well. At this point, I told our parents that I was going to propose. I quickly went to the study to grab the ring and set up a camera to start recording. When Helen came back, she immediately questioned why the camera was recording. I couldn't think of a good excuse, so I told her to come here and took her hand. For weeks I had planned in my head all the things I wanted to tell her during the proposal; however in execution, I forgot and stumbled my way through only half of what I wanted to say (sorry, Helen!). Nevertheless, I laughed it off, and got down on one knee.