Dale (always depicted wearing a fisherman's bucket hat) had planned to spend his retirement traveling the country with his wife Irma in their RV, but she died from cancer before they were able to. Traveling on his own, he comes across Andrea and Amy during the outbreak and takes them in. Over time, he, Andrea, and Amy bond, and he finds their friendship invaluable in getting past the grief he has over Irma's death. Throughout the first season, Dale is shown to be a self-sufficient man, ever watchful of the changing dynamics among the survivors and is particularly protective of Andrea and Amy. He also provides the group with a variety of modern conveniences to make their situation more bearable.

Dale first appears in the series premiere "Days Gone Bye", where he is shown with Amy in the camp of survivors outside Atlanta, hearing Rick's calls over the radio but it does not get through and Dale insists Shane try but they are unable to reach him. Lori insists they put up signs to warn people away from Atlanta to prevent them going into the city, as it is overrun, and Dale supports this but Shane rejects it. In the episode "Guts", Dale keeps watch on the camp from the roof of his RV, and watches Carl while Lori scavenges for food, and later receives T-Dog's radio call from the rest of the group in Atlanta. In the episode "Tell It to the Frogs", Dale greets Rick and the others when they return to camp, and helps Glenn strip a car he had stolen. In the episode "Vatos", while on lookout Dale notices Jim inexplicably digging holes on the hillside and becomes concerned, bringing Shane, Lori, and others to talk to him. Jim cannot explain why he is digging but says it was because of a dream he had. Later, the campground is attacked by walkers, and Amy is among the camp members killed. Jim then recalls his dream and why he dug the holes – to bury their dead. In the episode "Wildfire", Daryl and Dale want to kill Jim after they learn he was bitten in the attack, but Rick stops them. Dale attempts to comfort Andrea after her sister's death by telling her how much having the two of them to take care of meant to him. Dale later witnesses Shane's temptation to kill Rick over Lori's affection but says nothing to the others. The group decides to travel to the CDC, and when Dale's RV breaks down along the way, Jim is left behind at his request. In the episode "TS-19", they find relative stability at the CDC for a brief time before the building is revealed to be connected to a timer, which will detonate the building. Dale is willing to stay behind with Andrea and die with her when she refuses to leave, but she is convinced at the last second to save both of their lives.

In the second-season premiere "What Lies Ahead", Dale is greatly concerned about Andrea's well-being following her attempt, refusing to give her back her gun. At the same time, he is deeply invested in the search for Carol's daughter, Sophia, as evidenced by his lying to the group about the RV being broken (so that searching for her would be their primary focus). In the episode "Bloodletting", Dale believes that T-Dog has contracted a blood infection from a wound he received they search for antibiotics; Daryl eventually brings some antibiotics to them that Merle had in his stash of drugs. In the episode "Save the Last One", Andrea proves to Dale that her suicidal tendencies have diminished, and he returns her gun. In the episode "Cherokee Rose", Dale and the rest of the group arrive at Hershel's farm, and set up camp there. He helps the group try to retrieve a walker from a well, but the plan backfires. In the episode "Chupacabra", Andrea confuses Daryl for a walker, and shoots and injures him despite warnings from Dale. In the episode "Secrets", Dale's distrust of Shane begins to grow as he notices Shane's increasingly reckless behavior and dangerous influence he is putting on the group (most notably Andrea). Dale confronts Shane, but he threatens Dale. In the episode "Pretty Much Dead Already", Dale tries to hide the group's weapons, but Shane finds him in the swamp and retrieves them despite Dale's bluff to shoot Shane. Returning to the farm with the guns, Shane opens the barn that Hershel was hiding walkers in, and gets the rest of the group to shoot all the walkers. In the episode "Nebraska", Dale keeps an eye on Shane, and warns Lori about his suspicions that Shane killed Otis. In the episode "Triggerfinger", Dale tells Andrea that he feels Shane is dangerous but she does not believe him. In the episode "Judge, Jury, Executioner", Dale puts his issues with Shane aside when it comes to dealing with the fate of an outsider. Despite efforts to keep the group from murdering the outsider, he is outvoted and disgusted with the group's "survival of the fittest" mindset