Courtney and Woody probably should have met at least 1000 times before they actually did. Both attended UW-Madison around the same time, and spent time with the UW crew team--Woody as an actual member, Courtney as party goer. Despite overlapping friend circles, they weren't destined to meet until several years later. Their mutual friend, Mickey Gibson, introduced them at the dart board at Zorbaz during a trip to the cabin. Courtney's first thoughts were that Woody was tall and had an intense Minnesota accent. Woody's first impression was that Courtney was vaguely intimidating fresh back from living in New York. Over the summer, they became friends and those feelings quickly developed into something not nearly so platonic. From shared jet ski rides to haunted house trips, Courtney and Woody quickly found they couldn't live without each other.

Woody knew he wanted to propose at one of Courtney's favorite places and where they first met: her family cabin. Woody brought in the help of his mom and Courtney's mom and sister to come up with the perfect proposal. Under the guise of "taking family photos", Woody brought Courtney down to the lake where he handed her a sticker he claimed he'd bought for their shared Yeti cooler before getting down on one knee. Courtney was more than a little shocked--Woody had put a concerted effort into convincing her he wasn't planning on proposing any time soon--and even more surprised when both of their families appeared to congratulate them and celebrate.