Maybe it is noticeable, or maybe it is not; however, it has become pretty clear what is the relationship pattern for the unfortunate Sam Winchester. Although Dean is the guy who is known to be the ladies' man in the TV series, there is a lot to discuss about his little brother as well. "Supernatural" has never been one of those TV shows to put romance on the cover page, however, some things cannot go without being mentioned.
The ghosts of relationships past
It all started when Dean broke into Sam and Jessica's apartment to bring the life-changing news of "Dad is on a hunting trip, and he has not been home in a few days".
It only took that to start the chain reaction of basically 12 seasons of "Supernatural", and put a 360-degree turn on Sam Winchester's life. He revealed that he was planning on marrying Jessica, his girlfriend of roughly 4 years, and build an "apple-pie" life with her. That most certainly did not go as planned. He came back two days after a ghost hunt with Dean, only to find his life in flames, literally. It took him a year to get over her, and even then he never actually forgot her.
After Jessica, the fans were delightfully surprised to see Sam find another person to fall for. At the end of the second season, the Winchester brothers were investigating a werewolf case. After an odd turn of events where Madison, the seemingly innocent girl turned out to be the werewolf, they had to find a way to protect her from her worst enemy, herself.
In the episode, Sam and Madison hit it off instantly, and as it turned out, she died in front of him too.
When dealing with the horrendous death of Dean, Sam found comfort in the strangest of places, a demon. Ruby was there for Sam. She helped him save his brother, save himself, and try to get over the death of Dean as well.
That is not all she did. We still do not know if what was felt between Ruby and Sam was real; however, there was definitely something there. Obviously, we cannot forget the horrible things she did like, help jump-start the apocalypse or be a follower of Lucifer. In the end, Sam was the death of her too.
The last one to die for him
One of the girls, that Sam almost had a relationship with, was Sarah. She was smart, brave, and definitely a good kisser in the episode that she was introduced into the show. She and Sam immediately starting crushing on each-other and although Sam feared she would Die in his hands, she did not. Not until 7 seasons later, when they met again. Sarah was a wife, a mother and a woman who had seemingly found her happy ending. Unfortunately for her, Crowley in an attempt to stop Sam from completing the trials that would close the Gates of Hell killed her too. Not to mention the death of Amy Pond, Sam Winchester's first kiss. Although she turned out to be a monster, the real surprise was Dean killing her in a plot twist in the end of the episode.
The only women in his life that did not die, were Amelia, a few causal hookups, and Becky (although she does not really make the cut). Basically being involved with Sam Winchester romantically has a 81.6 percent death rate. Sam Winchester is in all meanings of the word, a hero, but as Charlie put it he "does not have luck with the ladies".
