Supernatural might not be known for its power relationships but that doesn't mean that there weren't some really interesting pairing on the show. In fact, Sam, Dean and Castiel have been linked to various different women over its 15-season run. Some pairings were memorable while others were quite forgettable.
Sadly, for a hunter or angel neither are blessed with the gift of love, at least not lasting love but that doesn't mean they don't try. Let's take the time to go through some of these pairs and see if they really were a match made in Heaven.
Sam Winchester & Amy Pond
Sam isn't exactly known for being the more sensible of the two brothers. He lets his emotions sometimes run wild, resulting in him not seeing the dangers that will take place in the larger frame of things. Sam met Amy when the two were teenagers after Sam saved her from a group of boys. Sadly, Amy was in fact a kitsune that had murdered a few people. Sam was willing to let her live simply because of their past but unfortunately, Dean had to make the hard decision to put her down.
Castiel & Meg
It is sometimes hard to understand Castiel and his never-ending path to relate to humans. Every time he appears to show some human feelings his angel conscience stands in the way. One of the few cases, when this doesn't happen, is his relationship with the demon Meg. At first, Meg uses Castiel for protection but after a kiss, realizes that she has true feelings for him. She even goes so far as to protect and die for Castiel. Which makes this one of the few Castiel romances where the feelings on both sides were mutual.
Dean Winchester & Anna Milton
Troubled souls oftentimes find each other. Sometimes the pain and suffering that connects them allow them to create something new and beautiful, while other times it just opens up old wounds.
Dean began a relationship with Anna unaware that she was an angel. The two found comfort in each other's arms due to the fact they both knew what it was like to feel abandoned. Sadly, their love was not meant to be due to them being on opposite sides of a war. While their love was brief they did have some touching moments before her ultimate demise.
Dean Winchester & Cassie Robinson
Not everyone is cut out for the world of a hunter. To those who were unaware of the supernatural's existence, a world of living nightmares would just be too much to bear. Unfortunately, that was exactly the case when Dean Winchester met the then-college student Cassie Robinson on a hunting mission. The two found brief love but once it was revealed to her what Dean did for a living the relationship abruptly ended. They were able to rekindle it years later but Dean was forced to move on from the relationship due to always being on the road.
Castiel & April Kelly
While Castiel has mostly shown an indifference to love for the most part on Supernatural, there have been a few times where he has been subdued, even if it was momentarily by carnal attraction. One such occasion come about when he met the reaper April Kelly. They had a ionate one-night stand but after realizing she was just using him for information on Metatron, he broke the relationship off. Shortly afterwards, April was killed by Dean Winchester thus ending for good her seduction of Castiel. It was never shown whether Castiel had true feelings for her.
Sam Winchester & Ruby
Some relationships are just toxic from the beginning. Not to mention the fact that both Sam and Ruby were on opposite ends of the moral spectrum and the fact she was an actual demon, the same demons Sam and Dean hunted made it even more unusual.
After becoming hooked on demon blood Sam found comfort in his former enemy Ruby but unfortunately Ruby was using Sam as a means to free Lucifer, the person she truly loved from his prison. Thankfully Sam was able to get his revenge by ending her before she could do more damage.
Dean Winchester & Robin
Being a hunter presents some noticeable problems for a young man or woman. The idea of always being on the road along with the potential that a monster will go after someone they care about makes them oftentimes quite distant from those around them. However, as a teenager, Dean did find love with a girl named Robin. Like always, Dean didn't get to stay with her but they did have a moment where they reconnected their love even if it was briefly. To Dean, she was the one that he let get away.
Castiel & Daphne Allen
Castiel isn't exactly known for his romantic acts nor will he ever be considered another Casanova. In fact, Castiel rarely shows any emotion for anyone other than the Winchester brothers. One could even argue that Dean is his true love and not be mistaken. Though, when Castiel acquired amnesia he did fall in love and marry Daphne Allen who used his healing powers to help the sick. After regaining his memory he bolted from the relationship and up to the present day has shown no interest in reconnecting with his former wife.
Dean Winchester & Jo Harvelle
On Supernatural there are less than a handful of characters that were meant for each other but Dean Winchester and Jo Harvelle would have and should have been the perfect match.
As a hunter, Jo understood the life that Dean faced and accepted the fact she was in it for life. At times, she was in the thick of hunting with Dean and Sam and never shied away from any threat put in front of her. Both Dean and Jo cared deeply for each other but sadly, Jo met her demise far too soon for love to truly blossom.
Sam Winchester & Amelia Richardson
Love might not always be in the air on Supernatural but that doesn't mean that there were not some close calls where one of the Winchester brothers almost called it quits for a chance at love. While Dean was stuck in Purgatory, Sam met a local veterinarian and after a few awkward encounters hit it off with her. However, unbeknownst to them, Amelia's husband was still alive resulting in them reconnecting. Even though Sam was smitten with the love bug, he decided Amelia and her husband deserved a chance at happiness.