Ben behaves very similarly to Dean Winchester, who had a fling with Lisa nearly nine years prior to Ben meeting Dean. While Lisa insists that Dean is not Ben's father, the similarities seem very striking. When Ben and several other children are captured by the changeling, Ben helps Dean in freeing them.
Season 3EditDean comes to Ben's birthday party. Ben appears to like cars, AC/DC, and chicks. Dean begins to suspect that he may be Ben's father. Lisa denies this theory. Later, Ben's Nintendo DS is stolen by some bullies. Dean helps out by telling Ben to use physical force on the bullies. Ben gets his DS back and high-fives Dean. Lisa stands nearby, irate. As she ushers Ben to leave, Ben gives Dean a hug. Ben later gets taken by a changeling and Dean goes to rescue him. When Dean finds Ben, he frees him and the rest of the captured children. Ben helps the children escape. Dean returns Ben to his home, but must leave town again, despite his fond memories of Lisa and Ben, and his growing attachment to them.
Dean is now living with Ben and Lisa. Ben is about 11 years old and Dean is acting as his father figure. When a Djinn attacks Dean, Ben and Lisa are moved to Bobby's house for their safety. Ben also appears in Dean's hallucinations (one when they return to the house; the other, Ben drinking Azazel's blood). After the Djinn is defeated, Dean goes back for Ben and Lisa. In "Two And A Half Men", Dean, Ben, and Lisa move to a new home after the Djinn attack. There Dean catches Ben holding a gun from the Impala. Ben tells Dean that most kids at his age have held a gun and that he could help Dean in defending the family. He continues on by saying that Dean could teach him some hunter skills. This infuriates Dean and he yells at Ben, upsetting Ben to the point that he hides in his room for a couple of hours. He also calls Dean when Dean is working in order to get some advice on how to tell his mom he broke a vase.
Ben appears again in "Live Free or Twihard," when a now vampiric Dean returns to the house in a near-bloodthirsty craze, hoping to see Lisa and Ben one last time before he turns. As Dean is leaving Ben sees him and walks toward him, but Dean fears for Ben's safety and then shoves Ben away from him and runs away, leaving Lisa furious. Ben does forgive Dean and calls Dean in "Mannequin 3: The Reckoning". He tricks Dean into coming home so Dean will see Lisa going out on a date. This causes Dean to have a talk with Ben, telling him why he can't be with him and his mother anymore. Ben is angry at him for "walking out on [his] family", which upsets Dean greatly but his mind is made up.
|“||You say family's so important, but what do you call people who care for you? Who love you even when you're a dick? You know you're walking out on your family, right?||”|
— Ben to Dean
in Mannequin 3: The Reckoning
Dean later arrives on scene, killing demons and frees Ben and "Lisa". The "Lisa" (who is Lisa possessed by a demon) grabs Ben and puts a knife to Ben's throat. "Lisa" begins to lie about how Lisa hates Ben and how Dean really is his father. Dean manages to free Ben and Ben takes the knife. Dean begins to exorcise the demon, but the demon stabs Lisa's body. Dean continues to exorcise the demon, and once the demon is gone, Lisa is now slowly bleeding to death. Dean gives Ben the shotgun and a few quick pointers. Ben is still in shock but Dean snaps him out of it. Ben shoots one demon as they make their escape, then Sam shows up and takes the gun. Ben is silent for the whole car ride to the hospital, and stays that way in the hospital room. Ben is angry at Dean for putting his mother in danger (which was the exact reason why he left them), and he eventually leaves the hospital room, furious with Dean, and with the fact that his mother is almost dead.
Castiel arrives on the scene and heals Lisa. Dean also asks Castiel to do him the favor of erasing all memories of Dean from both Lisa and Ben's minds, instead inserting the idea that Lisa was injured in a car crash. Dean is heartbroken by this decision, but knows that it's the best way to ensure their safety, and to ensure that they would both be able to be happy, even though he will not be with them.