Ashleigh and Stephen

Ashleigh's Proposal in Aspen, Colorado

How We Met

Stephen and I met while both working at a hotel in Auburn, Alabama where we were both attending Auburn University. While he was a bellman, it was my first day working at the front desk. I was shadowing my trainer on how to check in a guest while Stephen was waiting behind the desk to see if the man needed help carrying his luggage up to his room. The man checking in looked at me and asked if the hotel was pet-friendly and I said, “Yes sir, it is”. I was just glad that it was a question I knew the answer to as I had been working there for all of 30 minutes at the time! “Oh well, do you allow barn animals in here?” and without even thinking since I was full of first-day-on-the-job nerves, I said, “Well, we keep him around” while pointing directly at Stephen. We hadn’t even been introduced yet and I had already called him a cow! I was so shocked, mortified, and embarrassed that those words even came out of my mouth! Once the man left the front desk, I turned right around to Stephen, hardcore blushing, and finally introduced myself while reaching out to shake his hand. He looked me right in the eye, shook his head, and walked away without even the slightest hesitation! And obviously, I thought he was really cute and here I was insulting him on my very first interaction with him. I thought all hope was lost. It took probably half the eight-hour shift before he came around to even talking to me and we were introduced officially with no barn animals involved. Little by little, shift by shift (which our manager was totally scheduling us for the same shift since she knew we’d be great together), we eventually started dating and a little over two years later, he asked me to marry him!

How They Asked

When I was growing up, my family would go on ski trips to Aspen, Colorado every other year or so and it is one of my absolute favorite places in the whole world. When Stephen and I started dating, I knew it was somewhere I wanted to show him and make our own memories. We never really knew when we would get to go, but we knew it would be a first big trip together as a couple. The opportunity finally came during my spring break as a senior in college as a last big celebration before I entered the real world.

The weeks leading up to our trip, the entire state of Colorado was getting dumped with snow as winter storm after winter storm was hitting the ski areas. This was great news for us as we were going to snowboard, but wasn’t so good for Stephen and his proposal plan (we’ll get to that in a minute). By the grace of God, we were able to land at the local airport since, of course, a snowstorm had rolled in that day. But not without a hitch – the airline had lost Stephen’s checked bag so he didn’t have any of his real winter clothes or snowboard gear (good thing he was carrying the ring in his carry-on!) With it snowing nonstop that day and into the night, our walk around downtown was so magical with the fresh snow all around us. But little did we know that night there was an avalanche outside of Aspen that had shut down roads to the backcountry. And little did I know that this would cause Stephen the most stress and anxiety he had ever had in his life!

We woke up the next day to over a foot of snow and I was very anxious to get out on the slopes since these were the best ski conditions I could remember! But, Stephen had scheduled lunch plans for us at Pine Creek Cookhouse which is a beautiful restaurant in the backcountry of Aspen (maybe you can see where this is headed) and we would have to take a horse-drawn carriage to get to there. However, Stephen gets a text from “a friend” (who was actually his photographer, Ross) who just told him that the road to the restaurant was closed because of the avalanche. I was disappointed, but nearly as much as Stephen because this is where he was planning on proposing! Scrambling to make a new plan with Ross without me finding out, I’m pretty sure Stephen was taking 10 years off his life with the amount of stress and anxiety he was feeling.

Where to Propose in Aspen, Colorado

With me totally having no idea what’s going on, I got ready to head downtown to get Stephen some more ski clothes and have lunch. We headed down to hit the ski shop so Stephen could finally get on the mountain. When it was time for him to try on some new snow boots, he refused to take off the right boot that he was wearing and would only try on the new boots on his left foot. I thought he was just being a stubborn boy not wanting to put the effort into trying on new shoes and became quite frustrated with him.

Who would buy snow boots without trying them both on?! Loaded down with shopping bags filled with ski clothes, he had the lady put them behind the store counter to “come back later to pick them up”, which I thought was odd, but nothing too crazy. The restaurant we wanted to go to for lunch wasn’t open yet, so we decided to walk around the town to kill time. Nothing seemed too out of the ordinary until Stephen started insisting we go down certain streets in a town he had never been to before.

After about 20 minutes of walking around, we turned the corner towards the main walking street in Aspen. I noticed a photographer kind of just hanging out and it finally clicked: Stephen was about to propose.

Hand in hand, we walked down in between these beautiful snow covered trees until we reached the middle of the street and he “needed to fix his [right] boot” when actually he was getting the ring out of it! That’s why he was being so stubborn about trying on that dang new boot in the store because he was hiding the ring in his!

He took my hand to turn me so I was facing him and knelt down on one knee and said, “Ashleigh, we have been planning this trip since we have been together and I would love to plan the rest of our lives together. Will you marry me?” Of course, I said “YES!” and we both started crying (I more like sobbed). I could not have imagined nor planned a more beautiful, romantic, or simply perfect proposal from the most perfect man that I can not wait to spend the rest of my life with!

Wedding Proposal Ideas in Aspen, Colorado

Special Thanks

Ross Daniels
 | Photographer