Hillary + Jason | Calgary Winter Engagement Photos

calgary winter engagement photos sunset dusk night time

Gah!! I can’t get enough of these two. We had such an amazing time for Hillary and Jason’s Calgary winter engagement photo shoot that not even the chilly wind could dampen our spirits. Alright, I admit, towards the end of the photo session when the sun went down, we were pretty much ready to jump into a pile of blankets by then.

I have a huge thing for couples with big height differences so these two are really close to my heart. I love looking at these photos, even after it being such a long time since we did them together (umm, I’m so behind on blogging…!). The way that Hillary and Jason look at each other and laugh together is nostalgic of two teenagers in love. They couldn’t get enough of each other! I’ll let them do the rest of the talking on this blog below…

The age old question… how did you two meet?
Hillary and Jason: We first met 14 years ago working at the same company. We were always friendly but never in a million years did we think we’d end up together. Jason was in a long-term relationship and Hillary eventually left the company to pursue other interests. We were able to see the changes in each other’s lives over social media and in 2014 Jason messaged Hillary out of the blue. Jason had always thought that Hillary was cute and Hillary always admired Jason’s fun-loving personality. Daily messages turned into casual lunches that turned into dates. It’s still a bit surreal that we’re together.

How did the proposal go down?
Jason: I had the ring for two months before I proposed. Hillary’s parents spend the winters in Palm Springs and I wanted to wait and ask her Dad for his blessing before I asked Hillary. When he finally came home for Christmas I was so nervous to ask him. It was the most uncomfortable I’d ever been. I think he knew what was coming and enjoyed the moment. He gave me his blessing and I put the plan into action.
Hillary: It was a cold and miserable December day. I had had a tough day at work and was coming in with a carload of things. Jason normally helps me unload but he was nowhere to be found. I shouted for him but he didn’t answer. I saw paper on the floor and felt annoyed that he couldn’t pick up his things. After two more trips to the car I was starting to empty my baskets on to the counter when I noticed that the paper on the floor was actually an envelope that said “Memories” on it. I opened it and found a photo of us inside. Then I realized that there were envelopes all over the floor, each with a cute message and more photos inside. The envelopes led me on scavenger hunt through the house where I finally opened the door to our bedroom and found Jason waiting down on one knee. It was amazing. I have to admit that after the third envelope I clued in to what was going on and raced through the envelopes to get to him. Later I realized that he had selected photos of us to match each clue on the envelope. There was a lot of thought and detail put into each one!

What are your common interests?
Hillary and Jason: We really enjoy going on random adventures. For us a quick errand can turn into an entire afternoon exploring a new part of the city. We’ve been on a few different road trips where we’ve found some unplanned sights that ended up being highlights. We love to go for walks and bike rides by the river or sit on our new front porch and watch the world go by.

Share a fun memory with us!
Hillary: The first time I met Jason’s parents was significant for me. They are from Nova Scotia and had planned a trip to visit. We were a relatively new couple so I wasn’t sure how much time we’d be spending together that week. Jason and his family included me the entire visit. I was so impressed with Jason’s ability to make sure that everyone was happy and enjoying the trip. We went to the mountains, Jason his took his Dad to a Flames game and his mom and I went to bingo. There was shopping, fabulous meals and lots of laughter. It was a wonderful week and by the end of it I knew I wanted to be a part of his family.
Jason: I don’t know if there was one defining moment for me. I had known Hillary for a long time and always had a secret crush on her. When we finally got the opportunity to get together we just really clicked. She’s very thoughtful of people’s feelings. She is always looking out for others before she looks out for herself. She has strong family values, which I love. We have fun wherever we go.

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