Adam and Kate

The relationship between Adam Milligan and his mother, Kate was an extremely close one that was mainly due to the fact that, for the first twelve years of his life, Adam only knew Kate as his primary caregiver. The two were very close and enjoyed doing many fun things with each other and taking special trips with each other. Some of Adam's fondest memories are the memories with his mother. He especially remembers times when he was sick, and his mother would situate him on the sofa and then make him cream of mushroom soup and they would lie on the sofa together and watch movies that they both liked together. When Adam turned eleven, Kate started leaving him alone at night while she would work nights in the ER as a nurse. She did what she could to provide for Adam and Adam grew extremely defensive of his mother if he thought people looked down on her. To Adam, his mother did what she could to provide for him and he loved her for that. When Adam turned twelve, he and Kate started seeing his father, John Winchester after Adam begged Kate to call him. She did and they enjoyed an easy-going relationship with John.

However, in 2004, Adam was infuriated with his mother after she started dating a real jerk by the name of Davidson Miller. The man was abusive to Adam and never treated him with the respect he deserved. When Kate refused to see the problems, they had one of their biggest fights when Adam moved out of the home and temporarily moved in with his grandmother until John came to get him. When Kate finally broke up with Davidson, John returned Adam to her and after that they started doing more things as a family, something that Adam enjoyed immensely. In spring 2005, they took a trip to Yosemite National Park in California. It was one of the last times that they would have as a family before John mysteriously cut off contact with them.

In early 2006, Adam is devastated when his mother is murdered. He doesn't know the exact circumstances surrounding her death until he meets up with his half-brothers and learns that his mother was murdered by a demon and that his family hunts demons for a living. He has no choice but to learn how to defend himself. He fiercely holds onto the memory of his mother and desperately misses her even two years after his death, he still misses her and grieves her but rarely shares his grief with his brothers or father even though they know exactly how he feels from losing Mary many years previously.

In 2007, he was visited by Kate in a dream he had. The dream took place at their old house on an old trail they always walked together. Adam begs Kate to come back but she gently reminds him that she can't and that she loves him more than anything.