The CW show Supernatural is in its final season and the Winchester brothers are about to lay down their rifles and bottles of holy water. Given the nature of the show and the line of work the brothers are in, they haven't had a lot of luck when it comes to romance.
However, in the course of fifteen long years, there have been characters who have shared some romantic moments with Sam and Dean. As far as Sam is concerned, we know that his one true love, Jessica, died under shocking circumstances in the very first episode, thus forcing him to join his brother and becoming a full-time hunter.
There were others, however, who might have made good partners for the younger Winchester.
10 Lori Sorenson
Lori appeared in the season 1 episode, 'Hookman' as the daughter of the local pastor. The boys started investigating the murders of Lori's boyfriend and roommate and realized that they involved the urban legend of the Hookman.
Lori was literally the first woman after Jess who seemed to attract Sam and the two shared a kiss when Lori started having her meltdown. However, Sam was still far from over Jess and even though Dean told him that they could hang around even after the case had been solved, Sam decided against it. However, seeing that Lori had herself been a victim of the supernatural, she would have made a suitable partner for Sam, knowing what he did.
9 Sarah Blake
Sarah Blake was the daughter of an art dealer who had sold an old haunted painting that was getting people killed. The chemistry between Sam and Sarah sparked off almost as soon as they met.
However, at the time, Sam was still grieving over Jessica and feared that everyone he loved would end up dead. He let Sarah go and met her years later only to see her get killed with a witch's spell. Sarah had a definite connection with Sam but like so many others, their love story was doomed from the beginning.
8 Amy Pond
Amy was one of Sam's lovers from the past. Amy was a kitsune, a bit like a werewolf. As a young boy, Sam had let her escape after he and Amy connected even though he realized she was a monster.
Years later, Sam comes across some killings and traces them back to Amy Pond and finds out she has started killing for her son. He lets her go once again but Dean finds out about Amy and stabs her in the heart. Of course, given that Amy was a monster, she had little chances of being with Sam in the long run but she would have made a caring partner for him for a short while at least.
7 Madison
In the episode 'Heart', in season 2, Sam met Madison and connected with her instantly, only to find out that she had recently become a werewolf. The brothers try to save her and reverse the lycanthropy but to no avail.
After a night of steamy sex with Sam, Madison turns again and in what is still one of the most heartrending scenes in the series, Sam shoots Madison in the background as Dean involuntarily sheds a tear. Madison was the only person Sam actually cared for more than anyone else since Jessica died and had things not taken a tragic turn, she would have made a perfect partner for Sam.
6 Amelia Richards
When Dean ends up in Purgatory, Sam spends the year with Amelia. The romance between Sam and Amelia is mostly shown through flashbacks and it never quite evolves, possibly because Sam is in a strange state of mind, with Dean having disappeared without a trace.
Amelia's presumed dead husband comes back, but even then she is ready to leave with Sam. She gives him a choice, and Sam chooses not to go with her. In true Supernatural style, Sam is not meant to be with any woman he truly loves, but Amelia made him happy and could have made a good partner for him.
5 Eileen Leahy
Eileen was a badass hunter who first appeared in season 11 when the brothers were pursuing a banshee. She was a legacy of the Men of Letters and was killed by hellhounds set on her by Arthur Ketch, an agent of the British Men of Letters and an antagonist at the time.
In season 15, Eileen comes back, first as a ghost and then in the flesh, when Sam performs the resurrection spell on her. The two bond immediately and there is a hint of a budding romance as they kiss tenderly. Of course, Chuck uses Sam's weakness for Eileen to mess with them, and Eileen leaves eventually realizing her vulnerability. But she would, in fact, have been perfect for Sam, being a hunter herself and knowing the dangers involved in their everyday life.
4 Bela Talbot
Bela was the attractive young woman who locked horns with the boys as early as in season 3. She was the peddler of supernatural items and met her untimely end when the ten years she had been given in her crossroad demon deal were up.
Although Bela had obvious chemistry with Dean, it was Sam who was shown fantasizing about her in a rather hilarious dream sequence that involved black lingerie and making out. Bela and Sam would have been an interesting couple, always at each other's throats but also insanely hot together.
3 Genevieve Padalecki
In 'French Mistake', Season 6, the audience along with the brothers was transported into an alternate reality where Sam, Dean, and Castiel were called Jared Padalecki, Jensen Ackles, and Misha Collins respectively and were actors on a show called Supernatural. Jared was even married to a woman who was really Ruby, and had an alpaca in the backyard!
As the actors parodied themselves, and everyone wondered why Jared and Jensen were behaving oddly, perhaps Sam from this world could have stayed back to build a rich, happy life for himself in the other universe. Although one can assume that he would have been eventually caught when the real Jared showed up, at least he would have a stable home, income, and a beautiful wife to come home to for a while.
2 Velma Dinkley
Supernatural has been sprinkled with generous dollops of humor during its long run and one such fun episode was the crossover 'Scoobynatural' in season 13. The boys and Castiel got sucked into the world of the iconic Scooby gang and teamed up with them to solve a mystery.
Although Dean spent his entire time trying to woo Daphne away from Fred, it was Sam who actually scored without trying. Velma Dinkley took an unexpected liking for his shoulders and even planted a kiss on our blushing hero. Although this was never meant to be, the idea of Sam and Velma, the two intellectuals, being drawn to each other is kinda fun.
1 Lucifer
Okay, this may sound bizarre since Lucifer clearly tortured Sam out of his mind, but the two actually made quite the couple.
Either because Mark Pellegrino's Lucifer was a hoot or because Jared Padalecki does an exceptional antagonist when he has to, the two were actually quite a well-adjusted couple. If one wanted to go dark side, and god knows the show is dark enough, it might not be a stretch to imagine Sam partnering with Lucifer in the end, as was the big plan all along, and wreaking havoc on the world while Dean, Cas, and Jack trying to save the world from him.
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