After moving to Chicago, Anna joined a random kickball team to meet new friends. After playing on that team for several years, Anna met Josh Fox who lived across the street from Jonquil Park, the field Anna played on. Josh recruited her to play with his kickball team that upcoming 2013 summer season at Brands Park. Ryan had already been playing with that team for a couple years so he was close with everyone. After each game they would all go out for drinks, at first Anna didn't join, but eventually she gave in to Josh asking every week. At the time, both Anna & Ryan were in long-term relationships, but because they were the closest in age they always got along really well. They remained close friends, while dating other people, and eventually when both relationships ended they started spending time together without the whole gang.

The progression of the relationship was slow at first, but finally in August 2015 they began officially dating. Once they were official it was off to the races from there! That year they spent the holidays together and introduced one another to their families, took several trips, went camping & hiking, and started looking for a home to buy. In December 2016 they bought a condo in the Avondale neighborhood of Chicago and immediately started renovating. They joke that they were urban camping when they didn't have hot water for 3 weeks or a functioning kitchen - making all their meals on a George Foreman grill or in the microwave. One and a half years later, they are still working on the home, and love living together with their dog & cat.

The morning of March 3, Ryan asked Anna to go for a run. While Anna isn't an avid runner like Ryan is, she reluctantly decided to go. They showed up to Brands Park where they originally met, 5 years prior. After walking through the park they stopped at a bench and it is here where Ryan got down on one knee and proposed. When they ran back to their house, Anna was afraid that she would lose the ring so she ran with clenched hands all the way home where champagne was waiting for them.