One of my favorite things about my career is hearing all the amazing ways couples find each other. The universe really tested bringing Jessica and Will together and it was only by a hair’s breadth that they ended up going on that first date that would lead them to fall in love.

Jessica and Will met in January 2020 while living in Chicago. Their first date was a Wednesday night, during a freezing, snowing winter in Chicago. The weather was so poor that both Jessica and Will seriously considered canceling their date, but something inside both of them decided to push through the weather and go for it.

Sparks flew on that cold and snowy night, and after their first date they found every excuse to see each other again and again in the days that followed, making their relationship official.

Three months into dating, the 2020 pandemic hit and Will and Jess found solace in time spent with each other, filling their days with cooking, watching shows or playing board games together.

Falling in love together, Jessica moved in with Will and together they got their adorable Golden Doodle pup, Alice.

After a year of living together, Will planned a trip to fly to Oregon to visit family and head to California to explore Yosemite Park.

After a grueling 9-mile hike into the wilderness, Will and Jessica drove to another location in the park, and Will proposed to Jess by while family snapped photos and took videos.

Last year, Will and Jessica traveled cross-country to move to Southern Oregon, stopping at 4 National Parks along the way.

They are currently searching for the perfect starter home in Vancouver, OR, and are planning their wedding celebration in September 2023 at Oswego Hills Winery.

For their engagement session, we took our own mini-hike into the Columbia River Gorge and were treated by the most gorgeous autumn sun for a calm golden hour by the river.

Enjoy this selection of images from Will and Jessica’s engagement session, and leave a note of congratulations for them in the comments section below!