Sam's college girlfriend, Jessica, was killed on his ceiling like his mother. Her death hit Sam hard and set him on the road with Dean. He fell for Sarah Blake, but the job took him away. She ended up married with a daughter before she was killed by Crowley. Sam met Madison and they were instantly smitten. She ended up becoming a werewolf and Sam killed her at her request. Sam had an odd relationship with Ruby. She was his ally, his lover, his Demon blood supplier, and then foe. In the end, the brothers killed her. After Dean went missing, Sam finally found happiness with Amelia, but that was short-lived too when her presumed dead husband showed up alive. She ended up chosing Sam over her husband, but Sam had already left with Dean. Sam's love life has been filled with more death than happiness.