Dean Winchester

Around the beginning of Season 3, Episode 2 ("The Kids Are Alright"), Dean Winchester and Sam arrive in Cicero, Indiana to investigate a strange case involving a woman who believes someone is trying to kill her. Before Dean meets Ben, he visits his former girlfriend, Lisa Braeden, whom he has not seen for years. Dean is surprised to discover that Lisa has an eight-year-old son named Ben. At first, Dean simply wants to catch up with Lisa while helping solve the case, and he has no idea that meeting Ben will soon make him question what his life could have been like if he had chosen a normal family instead of hunting monsters.