Supernatural: 5 Ways Sam & Jess Were Perfect (& 5 Other Characters He Could Be With)

In the pilot episode of Supernatural, Mary (Sam and Dean’s mom) is pinned to the ceiling and burns to her death. Thus begins their journey as a family. John (their father) becomes a hunter to avenge Mary’s death, raising his sons to be hunters as well.

Sam’s story parallels John’s. He’s not hunting anymore and is getting ready to settle down with Jess. Coming home, he finds Jess pinned to the ceiling, burning to her death. Her death causes Sam to want to hunt and avenge her, just like Mary’s death did for John. Although Jess was barely in the show, her presence casts a long shadow. In many ways these two were perfect for each other and had an epic love cut too short. But there were also other characters that could’ve worked better for Sam.

10 Sam and Jess: In Alternate Realities/Dreams They Are Together

When Dean is put into a dream-world by a djinn, Sam and Jess are together. Matter-of-fact, they have a good life, one of stability. While this is Dean’s dream-world, it does show that even a skeptic like Dean understands the connection that these two had together.

Later, fans learn that Sam planned to propose to Jess. This shows that it’s likely that these two would have stayed a solid couple if it weren’t for Jess’s life being cut dramatically short.

9 Other Character: Amy Pond

Sam met Amy Pond when they were teens. Both of them felt trapped by their family-legacies. Sam was tired of the hunting life, even at that age. Amy was technically a “monster,” but she didn’t want to be one. They connected in how they felt like they were freaks and how they didn’t want to be like their parents. Amy actually killed her mother in order to save Sam. Then she asked him to run away with her.

These two shared more than a kiss when they were teens, they shared a connection that extended into their adult lives. Unfortunately, due to her lifestyle and Dean’s black-and-white thinking, that connection was cut short.

8 Sam and Jess: Had a Life and Home Together

When Dean goes to find Sam in the pilot episode, Sam and Jess actually live together. This is a serious relationship for both of them. It’s clear that they both feel very comfortable with each other. Sam’s other romances are often just while he’s working a case, so it could be a night or a week, it’s not like it was with Jess. These two had been together much longer.

The only glitch is that Sam didn’t tell Jess about his past as a hunter, but he wanted to protect her from the knowledge of the supernatural world.

7 Other Character: Amelia

When Dean is sent to Purgatory, Sam decides to stop hunting. It’s during this time that he meets Amelia. He’s with Amelia for a year, and during that time, he has a normal life with her. It’s something that he wants.

In truth, he fell in love with Amelia. Had he given her the opportunity, she would have chosen him over her long-lost husband. Really, she did choose him in the end, but Sam choose hunting over her.

6 Sam and Jess: She Helped Him Lighten Up And Feel Joy

Out of the two brothers, Sam is the more serious one. He has a hard time lightening up. Jess helped him with that. In the pilot episode, she insisted that he go to a Halloween party, although he was reluctant.

She got him to be part of a community of friends, and she was able to joke with him. All this helped him lighten up and feel joy, which is something that he needed. Sam’s early life was defined by tragedy. Jess had represented a joyful happy ending.

5 Other Character: Eileen

Like Sam, Eileen is also a hunter. She knows the hunter life, so they don’t have to hide their present or their past. Eileen had been Sam’s friend, but when he is able to resurrect her in Season 15, romance develops. In many ways, Eileen would be the perfect person for Sam. She’s tough, smart, caring, and sincere.

They care about each other, and she would never want to hurt him. When Chuck/God makes her hurt Sam, viewers can easily see the pain on her face. This could have been a great match had Chuck/God not gotten in the way.

4 Sam and Jess: They Celebrated and Supported Each Other

These two are each other’s allies. They lift each other up. All of Sam’s life, he wanted to be recognized and valued by his family. He wanted to be more than a hunter. When he decides to go for law school and tests really well, Jess celebrates him. She lets a friend know, so that more people can celebrate Sam’s achievement.

Knowing that he’s worried about his upcoming interview, she assures him that he’ll do well and get the full-ride. It’s not often that Sam has had people believe in him like that, so he seemed to beam under her encouragement and positive nature.

3 Other Character: Madison

In Season 4, Sam and Dean find out that their lives are a graphic novel series by Chuck (who they don’t know is God–at this point). To get more information on Chuck, they go to the publisher, and this is where fans learn about the extent of Sam’s feelings for Madison. The publisher tells them that the best parts of the series are when the brothers cry, “Like in Heart when Sam had to kill Madison, the first person since Jessica he really loved.”

From this, it’s shown that Madison was a very special person to Sam. Had Sam and Dean met her later in the series after they found a way to cure those who had been bitten, Madison could still be around.

2 Sam and Jess: He Still Loves Her

So much time as passed, and Sam has been through a lot since Jess died in Season 1. He’s suffered, learned, and grown. Despite all this time that has passed, Sam told Dean that he still thinks about her. He will always love her. Sam is just like his father, whose love for Mary never paled over time and distance.

In a sense, Jess is the perfect person and relationship for him. No matter how great others may be, they will never be Jess.

1 Other Character: Sarah

Sarah and Sam didn’t work out due to bad timing. Sarah was the first person he was attracted to since Jess’s death. They were able to connect over such a short time period. Sarah knew about Sam’s supernatural-hunting work, and she didn’t care.

When Sam tried to “protect” her from getting hurt by not starting something with her, she responded, “That’s very sweet and very archaic. Look, I’m a big girl, Sam. It’s not your job to make decisions for me.” Sarah would’ve been a strong partner for Sam, one who could call him out as well as encourage his good deeds.

About The Author