Dana and Ed were set up by mutual friends who thought they would hit it off. Dana was given Ed's phone number so she would know it was him when he called. Days went by and Dana didn't hear anything from Ed, so in true Dana fashion, she took matters into her own hands and reached out to him first. After texting for a few days, Ed asked Dana to get dinner and drinks. They went to a Halloween themed pop up bar followed by dinner at Bud & Marilyn's. Once Ed made a reference to "the implication" from It's Always Sunny in Philadelphia, Dana knew he was the one.

Ed's ultimate goal was to be able to surprise Dana with a proposal, which he knew would be a challenge - but he did it! Ed told Dana they were going to get dinner with another couple. Dana had mentioned how she loved the cherry blossoms that were in season at Fairmount Park, and Ed suggested they leave a bit early so they could stop at the park, stroll, and take some pictures with the cherry blossoms. They took a few selfies together and then to Dana's surprise, Ed dropped down on one knee and popped the question! He even hired a photographer to capture the moment.