In November of 2018, Anna had a friend in dorms that insisted her tutor would be a perfect match for Anna. She said that if they just went on one date, she wouldn't bring it up again if it didn't turn out well. Anna agreed since the tutor was a rather attractive guy and clearly he was smart if he was tutoring her friend. On 30 NOV 2018, Cam took Anna out to the most silent dinner at Dinosaur BBQ, where Anna was not fearful of ordering ribs and wings, followed by Anna's first hockey game. Anna and Cam managed to score free tickets to the Air Force v. RIT hockey game because her buzz cut just screamed military to some guy with extra tickets. Neadless to say the rest is history.

One year into dating, it was safe to say that both Cam and Anna could see themselves spending the rest of their lives together. However, because Anna had recently broken her leg and the ring that Cam had purchased to propose hadn't come in the mail yet, his plan to propose fell apart. Little did he know though, Anna had her own plans. Since Cam likes to boast his Irish heritage, Anna looked up a few Irish traditions including Bachelor's Day, and men and women traditionally wearing Claddagh Rings during the engagement. Although their anniversary fell on a different day than the traditional leap day and Anna didn't think Cam would prefer the traditional ring, she still wanted to propose. Anna set a reservation at Dinosaur BBQ and got a photo book printed with some of her favorite memories of the two of them with the back cover saying "Will you marry me?". Anna presented Cam the book after diner and had to stop him from flipping it over and not reading the pages before he got to the big question. Once he was nearing the end, Anna pulled out his band and was ready to pop the question when he got there. Needless to say, he said yes and they celebrated with dessert pie.