Anna and Dylan met at the University of Wyoming, and because of mutual sorority and fraternity friends they spent a lot of time with the same crowd. They went out in a group for Halloween just over a year after they met. “It was our first unofficial date, basically,” Dylan says.

“We were able to hang out all night,” Anna says. “That was probably the longest amount of time that we had consistently been able to sit down with each other, hang out and have fun,” Anna says. After that, “We would go on hikes and just be silly. We got to know each other on a much deeper level that way.”

On one of their hikes, the weather turned suddenly violent, and they had to run for cover. “We ended up having to hide in an inlet in the rocks,” Dylan says. “It was pretty scary; big hail and lightning at a high elevation.” However, the two stayed calm during this memorable outing. When Dylan decided to propose, he asked two close friends to hike with him and Anna to the same spot. Because of approaching bad weather (again) the experienced hikers practically jogged the two miles to the top. Once there, the couple climbed up to a lookout spot. “I pointed out a rainbow on the lake, and she turned her back to me,” Dylan says. “While she was turned away, I got down on one knee. When she turned back I proposed.”

Anna was shocked, though she had noticed something was a little off. “I kept asking, ‘Why are we in a rush?’ and no one was responding,” Anna says. That made her think that he might be proposing. “I tried to convince myself that he wasn’t, because I didn’t want to be disappointed if he didn’t. When I turned around and saw him on his knee, I was happy.”

The wedding was held nearly five years after they met. When Dylan saw Anna coming down the aisle, he says, “I was overwhelmed, in a good way, very happy, full of joy and excited. I could hardly believe what we were about to do.” Though Anna was nervous at being the center of attention, she says, “The second I saw Dylan I had tunnel vision, and I actually don’t even remember feeling nervous once I saw him.”

The two agreed that the wedding exceeded all their expectations. “My sister and my mom,” Anna says, “put everything together and made it so much better than Dylan and I could have ever done on our own.” Anna says the wedding was “fun and happy and a party,” and Dylan agrees. “There were so many close friends and family together—it really was family and fun.” 

—Margaret Snider

Anna and Dylan Cielo Estate Winery Timeless Classic Wedding by Carrie Ayn Photography

Anna and Dylan Cielo Estate Winery Timeless Classic Wedding by Carrie Ayn Photography

Anna and Dylan Cielo Estate Winery Timeless Classic Wedding by Carrie Ayn Photography

Anna and Dylan Cielo Estate Winery Timeless Classic Wedding by Carrie Ayn Photography