Ailish and I got engaged on September 7th, 2009, in Montreal.

We had our first date in August, 2007. We bought a house together in August 2008 and decided to take a trip to Vancouver to celebrate and decompress. So it made sense to head out of town in the late summer of 2009, too. We decided to go to Montreal and Halifax.

What Ailish did not know is that I had decided early that summer to propose to her. I knew Ailish was special from actually before I even met her in person, but I had this whole plan. You have to date someone for at least a year before you move in. And you have to live with a person for at least a year before you get engaged. Well, living together had worked out really well. I mean, apart from the fence, but we swore never to talk about that. I’ve heard people ask how you know if you should get married. I don’t really know the answer to that question. To me, with Ailish, it was obvious. I was very much in love with her and I knew she was very much in love with me. We were partners. We could tackle anything the world threw at us. I wanted to spend the rest of my life with Ailish.

So, I bought an engagement ring (after spending hours and hours and hours learning about different types of diamonds, different settings, styles of rings, trying to figure out Ailish’s ring size, etc.). I received Ailish’s parents’ blessing. And we were already planning a trip to Montreal and Halifax, so I figured what better opportunity?

I was so scared that I would lose the ring. I refused to put it in my checked baggage. I refused to leave it in the hotel room. I carried it around with me as we saw the sights in Montreal. And let me tell you, an engagement ring in a box is rather bulky. I figured I would probably propose either on Sunday, September 6th, or Monday, September 7th. We were leaving to Halifax on the 8th and I figured Montreal was probably more romantic.

So, the Sunday was a pretty good day. I mean, we had a great time wondering around Montreal, seeing the sights. But “pretty good” was not really what I was going for. I wanted to propose in our hotel room, in private, and when we returned to the hotel room, Ailish had received some emergency emails from work which stressed her out. So, Sunday was out and now I was down to one day. I mean, sure, I could have proposed in Halifax, but who knew Halifax would be so awesome?

Monday, September 7th, 2009. The most clear memory I have from that day is finding a little courtyard, sheltered from the street but open to the sky. We sat there for several hours, eating and drinking some beers, chatting and just enjoying life. It was just beautiful.

When we returned to the hotel room, I asked Ailish how she had enjoyed her day. When she responded, “Today was just the perfect day,” I knew my time had come. Ailish was on the bed, and I was on my knees on the floor. I remember telling her how happy I was that she had said that, because I had been waiting for the perfect day. I remember telling her how happy she made me. I remember telling her how I wanted to spend the rest of my life with her. And I asked her to marry me.

Ailish’s response was, “Are you serious?!?” I started to assure her that I was, that in fact I had an engagement ring, and before I was even able to get the little box open, Ailish had said yes. When she saw the ring, her eyes sparkled.

That evening, we celebrated by participating in a pub quiz, though I’m not convinced we stayed for the whole game. We then spent the next ten months calling each other ‘fiance’ and ‘fiancee’. :)

My wedding day was amazing and awesome and full of love, kisses, family, friends, and beer. But September 7th, 2009 was the day I knew that the love of my life was going to marry me.

Christopher Thompson
June 19th, 2011 1:53 PM

When you read the guides on picking out a ring size, they all tell you that you should either measure your girlfriend’s finger or you should measure another ring that she wears. The problem was, Ailish never wore jewelry. I mean, not even earrings. I had never seen her with a ring on her finger. And I really wanted the engagement to be a surprise. I must admit, I actually considered getting her _really_ drunk so she would pass out and I could measure her finger, but ended up deciding against it.

The engagement ring I ended up ordering was a good three sizes too big, but I figured it was far easier to shrink a ring than to expand it. Ailish didn’t care. She walked around wearing that ring for days, her left hand clenched so the ring wouldn’t fall off. :)

Christopher Thompson
June 19th, 2011 4:28 PM

Ailish O’Connor, I miss you. :(

June 19th, 2011 6:22 PM

Oh, Christopher, what a beautiful proposal!

You and Ailish made a beautiful life together. I’m sorry it had to be so short … but in the time you had, wow.

How sad to have had to say goodbye so soon.

My heart aches for you in your sorrow.

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