On February 11, 2022, Chet and Amy come to the hospital to collect the donations for the charity that he was working with. Later Chet sits next to Terry Randolph at Charlie's Pub. Terry had arranged to meet her dating app match at Charlie’s on Valentine’s Day. He will be wearing a teal colored shirt so Terry knows who he is. Chet is revealed to be wearing a teal colored shirt. Terry says it is nice to meet him. She worried he wasn’t going to show and he thinks she is trying pickup lines on him.
Terry explains that she saw Chet’s teal shirt and Chet tries to explain that he isn’t the person she is waiting for. She says she wasn’t sure about not sending each other photos and calls Chet "Tanner". Chet apologizes and says he isn’t Tanner. A man comes over and tells Terry that he is Tanner and their table is ready. Chet eavesdrops on Terry and Tanner's date and stops it when he can’t stand to listen anymore. Chet claims that Terry is his girlfriend and says he can’t share her anymore. Tanner leaves and Chet sits in his spot. They complain about being single and Chet says that Terry is beautiful.
On April 4, Terry gets a text from Chet that he is overseas for another month but he hopes to see her when he gets back. Terry replies that she wants to see Chet too and asks him to text with dates when he has them.
On May 9, Chet and Terry meet at the Metro Court Gardens for their first official date. Chet reveals that Terry found out about his prosthetic legs through text. Terry mentions that she was terrified to tell Chet she is a trans woman. Terry jokingly says Chet is no Tanner and they call him names. Chet says at least Tanner set the bar low and it shouldn't be too hard to surpass him. Terry tells Chet she will let him know on their second date. Chet enthusiastically says yes. Terry talks about someone she is having trouble with at the hospital. Chet and her exchange last names and Terry realizes the troublemaker, Amy, is Chet's sister.
At the end of the month, Amy applied Chet for a VA job in Chicago and Chet gets it. He didn’t apply for it and after eavesdropping on him and Terry, Amy feels guilty and confesses to them that she applied for him. He wants to stay in town but Terry convinces him to go as this is a dream job for him. He says if she doesn’t have a date next Valentine’s Day, she responds that he will be her first call.