Sam Winchester of Supernatural (Jared Padalecki) has led a very different kind of lifestyle compared to his older brother Dean (Jensen Ackles). His taste in food (he's the healthy eater), his soft sympathetic side for victims and even monsters, his educational background (he went to Stanford University) and even his love life (remember Jessica, Sarah or Madison?). Now, Sam doesn't usually have much luck with the ladies (they either die or it doesn't last), but there have been a few noteworthy romances compared to his brother's womanizing approach to relationships. One-night stands aren't typically Sam's thing (unless he's soulless). So, on display are Sam Winchester's best romances, ranked.
Velma Dinkley
In Season 13's "Scoobynatural", Sam is completely oblivious to Velma's obvious attraction to him. She repeatedly discusses Sam's "broad shoulders" and even takes control, stealing a kiss at the end of the episode, surprising Sam. This is both funny and adorable, as the chances of the two becoming a couple are highly unlikely but a nice thought anyway. It's also ironic, considering Dean spent his time trying to get together with and impress Daphne for the episode's duration, only to be unsuccessful and instead watching Sam have the opportunity of a beloved childhood cartoon character falling for him. It's not a perfect world, animated or otherwise, but the attraction Velma has to Sam makes the world look cute and innocent.
Ruby
The demon Ruby, first introduced in Season 3 (played by Katie Cassidy and later Genevieve Padalecki), manipulated Sam from moment one. She at first tells him she can help Dean get out of his crossroads deal (not true), and after Dean is killed and goes to Hell, Ruby steps in as Sam's hunting partner. Yet the depths of her betrayal are revealed in her plan to prepare Sam as Lucifer's vessel and breaking the final seal by killing Lilith.
She trained him to use his powers, got him addicted to demon blood and caused a whole slew of problems for him. We weren't sorry to see her go (we applauded when Sam and Dean killed her). In real life, Jared Padalecki married Genevieve, the second actress to portray Ruby, so in that instance it was his best romance.
Genevieve Padalecki
Speaking of which, in Season 6's "The French Mistake", each of Supernatural's main characters Dean, Sam, and Castiel (Misha Collins) hilariously played parodies of their real-life selves when Sam and Dean are cast into an alternate reality where they are actors in a TV show. In this alternate reality, Sam is married to Genevieve Padalecki. Though she does not play her real self exactly and Jared as Sam has no idea who she is apart from being Ruby, their interactions are farcical and memorable. Not to mention a noteworthy relationship (and episode) that we simply had to mention here.
Becky Rosen
Becky's (Emily Perkins) an enthusiastic Supernatural fan obsessed with the books and that is totally and irrevocably in love with Sam. We meet her a few times over the course of the series, and though Sam does not return her obvious affections, he tolerates her. However, in Season 7, Becky drugs Sam and gets him to marry her, resulting in an interesting and hilarious episode (when Becky runs out of the potion that drugs Sam, she hilariously ties him up in bed to get him to stay).
Becky's a good person deep down and she does seem to truly care for Sam, but unlike Sam's other relationships, Sam didn't return her feelings and was forced into a relationship he didn't want, hence it was less of a messy break-up on his part. Probably not the best potion for romance.
Amelia Richardson
In the year that Dean was stuck in Purgatory, Sam took up a relationship with veterinarian Amelia (Liane Balaban). The two lived together in Texas, dog and all. Their relationship was working until Amelia's husband, previously thought to be dead, makes a surprise return. Sam makes the difficult decision to give her another chance with her husband and leaves, though he truly wishes to stay. Considering this was the closest Sam ever got to his dream of living an "apple-pie life", we feel sorry that it didn't work out for him. We see much of their time spent as a couple in flashbacks, from their first meeting to Sam meeting her father. Later, Amelia gives Sam an ultimatum, and he chooses to stay with Dean, never knowing what might have been.
Amy Pond
Amy is a kitsune that Sam meets as a teenager. Initially unaware that she is a monster, Sam is attracted to her and the two later share a kiss. Sam reveals he is a hunter but lets her go and owes her one when Amy kills her mother to save him. Amy pleaded with Sam to run away with her, but unwilling to leave his family, Sam passes up the opportunity.
The two later run into each other again in Season 7, now adults, and when Sam finds out why Amy's been killing, he again lets her go, remembering what she once did for him. Dean kills her anyway, resulting in a rift between the brothers that they eventually settle. Still, the potential for a romance was great, and the two made big sacrifices on the part of the other. It could've worked.
Lori Sorensen
Early in the first season, we meet Lori (Jane McGregor), a young college student that is seemingly cursed with the worst luck in the world. She becomes intertwined with the "Hookman" legend, her boyfriend and roommate (and nearly her father) brutally killed. She and Sam connect by expressing their feelings regarding their losses (Sam's loss being Jessica) and share a kiss, though Sam stops it and admits that it's too soon for him. Sam and Dean save Lori before she is killed as well and put the legend on permanent rest. Dean offers to stay a few extra days so Sam can be with Lori, but Sam refuses and they leave. In this case, the timing was bad but the two could've bonded over their losses and shared something special, making this one of Sam's best, however unfulfilled, romances.
Madison
In Season 2, Sam meets Madison (Emmanuelle Vaugier). Unfortunately, she was bitten by a werewolf, rendering her one as well. Sam and Dean test out a theory to try to rid Madison of the curse, but tragically it doesn't work. Sam, who has fallen in love with Madison (his first love since Jessica), is faced with a broken-hearted Madison who has accepted her fate and asks him to kill her so she doesn't hurt anyone else (when she sleeps, she turns werewolf and kills, giving into her monstrous nature).
Sam tearfully takes Dean's gun and kills her. This was one of the times we cried with and for Sam, broken by the devastating loss as he was.
Sarah Blake
Sarah, played by Taylor Cole, appears towards the end of Season 1. She inadvertently becomes involved in one of Sam and Dean's cases, feeding them information about a haunted painting and discovering the truth of what's out there in the process. She bravely helps the two hunters destroy the painting and save the day, risking her life because she feels a certain responsibility for selling the painting to the victims. Dean tells Sam to "marry that girl", something that doesn't happen as the Winchesters' hunting lifestyle prevents any kind of happy ending for the two. Though, Sam and Sarah's interest in one another was the first sign of Sam moving on from Jessica's (Adrianne Palicki) death. Later Sam runs into Sarah again, though by then she is married and has a daughter, but is tragically killed by Crowley (Mark Sheppard). Sam never has any luck when it comes to happy endings; it's the curse of being a Winchester.
Jessica Moore
Though she died in the series' very first episode, we could see she and Sam had a good, wholesome relationship and that they loved one another significantly. Sam was even ready to propose. Jessica was beautiful and kind; brutally killed to push Sam back into the hunting world (something which Sam felt guilty for, especially since he foresaw her untimely death). It took Sam a while to feel comfortable with dating other women, and eventually he did avenge her death. Still we, alongside Sam, wonder what could have been since it was clear Jessica was "the one." Perhaps in another life (maybe even a spin-off?) Sam and Jessica could have the chance they never got, since their relationship was clearly Sam's best romance.
Sam had several one-night stands while soulless and a few one-night stands here and there when he was with soul, but that's part of the hunting lifestyle. For the most part, Sam either stays in relationships (until his significant others notoriously die), or else breaks up and leaves them, afraid that with his lifestyle they'll only end up getting hurt or worse. We do hope Sam gets some kind of happy ending in the show's conclusion next year, but considering Sam's past romances, it doesn't seem likely. Nonetheless, Supernatural has surprised us before--and could very well do so again.