In late-September of 2020, Anna was looking for love. She asked one of her friends if he could set her up with anyone, specifically an athletic, Asian guy. Connor fit the description and the two began chatting. Within a week and after countless hours talking over social media, they went out on their first date. They got teriyaki and spent the evening in Edmonds, looking out over the water at the Autumn sunset. The date continued with a drive around Seattle, stopping by for boba and more sightseeing. Connor was hooked and at the end of the evening, asked Anna to be his girlfriend. He felt something different, something he had never felt with another girl, and was eager to have her be part of his life. Anna was a little shocked by the immediate question but wasn't against the idea. She told him that, "We will wait and see", as she went home. A week later, they started dating and from then on, the two fell more in love each and every day.

The two were inseparable, doing everything together. As they grew closer together, they often talked about getting married. It was no coincidence that one day while Anna was away in Costa Rica for a school trip that Connor sat down with her Mom and Dad and asked for their blessing. After a long and thorough conversation, Anna's Mom and Dad gave Connor the green light.

Fast forward to the Combs' annual Cannon Beach trip. Connor and his family had been going there ever since he was little and to him, it seemed like the perfect opportunity to create an everlasting memory. It'd also give them an excuse to continue to go to Cannon Beach every year and keep the tradition strong. Once they arrived in Cannon Beach, a couple days go by doing typical touristy activities. One afternoon, Anna and the Combs family set out to walk around Ecola Park, just north of the historic town. Connor was nervous and even though he knew she would say yes, his mind was racing on what to say, how to propose, or the perfect moment to do so. On the contrary, the thing going through Anna's mind was the story of a cheesy romantic novel she had been reading from the local library. As the two walked towards the Western lookout, Anna kept going on about her story. Connor, not listening at all, was waiting for her to politely "shut up" so he could go through with his plan. Eventually, she stopped talking and the moment was set. Connor convinces Anna to stand near the edge as part of his "vlog" he had been making. As she stood by the edge, back facing to him, he pushed her off. Just kidding, that'd be horrible. He got on one knee and proposed, asking Anna, the love of his life, to be his fiancé. She said yes and the two rejoiced together as their plans of getting married and spending the rest of their lives together were slowly falling into place.