James "Sawyer" Ford knew how to be a ladies' man. He was one of Lost's most charismatic, passionate, and intelligent characters. He used these traits to seduce women for some of his cons, though he also developed genuine feelings for characters like Kate and Cassidy.
As Sawyer developed, he eventually ended up with Juliet. Their relationship proved to be the kind of positive relationship that he needed. While Juliet was the perfect partner for him, there are plenty of other characters he could've ended up with under different circumstances. These are the other characters Sawyer could've ended up with and the reasons why Juliet was the right choice for him.
10 Could Have Been With: Ana Lucia
Ana Lucia and Sawyer had sex once, but only as a way for Ana Lucia to get his gun. Despite this problematic encounter, other moments in the show proved that Sawyer and Ana Lucia could've worked as a couple. They both had fiery personalities and weren't afraid to push each other's limits.
Both could be sarcastic and make fun of each other. They were resourceful, resilient, and though neither of them sought leadership, others would look to them for leadership in a time of need.
9 Juliet: Commitment
Before his relationship with Juliet, Sawyer had never truly committed to a romantic relationship. His relationships with Cassidy and Kate didn't work out for a variety of reasons, an important one being his failure to commit.
With Juliet, he was able to settle down and they were able to build a life together while working for the Dharma Initiative. She helped him foster a kind of devotion that he'd never shown to anyone before.
8 Could Have Been With: Libby
There were never any romantic sparks between Libby and Sawyer, but a romantic relationship might've worked. When Sawyer was suffering from his gunshot wound as they crossed the Island, she was adamant about getting him the help he needed.
Libby was compassionate, but her past as a clinical psychologist allowed her to see through people's facades and help them unpack the insecurities and deeper issues holding them back. She was compassionate but tough and fiercely intelligent enough to be exactly the kind of partner that Sawyer needed.
7 Juliet: Sensitive
Juliet was sensitive to Sawyer's needs and she also helped him get in touch with his more sensitive side. Juliet was always there for Sawyer and knew what he needed to be happy, fulfilled, and to deal with difficult situations.
She helped Sawyer become more sensitive and he did things on his own like picking a flower for her that he thought she would like. Such a small, sweet gesture is something Sawyer had never done for partners in his past relationships.
6 Could Have Been With: Claire
After Charlie's death, Sawyer became more like an older brother to Claire and became fiercely protective of her. When Miles showed interest in her, he kept Miles away as he didn't trust him. When Martin Keamy and the other mercenaries attacked the group at the Dharma Initiative barracks, Sawyer ran outside and risked being shot to find Claire and bring her to safety.
If things developed differently and enough time passed, Sawyer and Claire's relationship could've morphed into something more romantic. He was already devoted to her and he showed with Juliet that he could become committed and settle down.
5 Juliet: Balance
Sawyer and Juliet balanced each other out well. He had a more fiery personality while she was more calm and composed. Both were passionate and highly intelligent, resourceful, and charming individuals, but these traits manifested in different ways.
They found common ground and admired each other's differences and strengths. They learned how to be a balanced team which later allowed them to work well as a romantic and committed couple.
4 Could Have Been With: Nikki
Sawyer and Nikki wouldn't have been healthy for each other, but they had similarities that could've drawn them together. They both knew how to manipulate and con people to get what they wanted. They could be attracted to danger and weren't afraid to face high stakes.
If the right opportunity came along, Sawyer and Nikki could've joined forces and watched their attraction to danger and high stakes develop into an attraction to each other. It probably would've been a toxic and manipulative relationship, but it could've worked for some time.
3 Juliet: Respect And Understanding
Sawyer respected and understood Juliet in a way that he'd never respected or understood a partner before. One of the best examples of this came when young Ben Linus was shot and dying. Sawyer had plenty of reason to hate Ben and didn't want to risk his neck to save him. Juliet, on the other hand, couldn't stand to see a child suffer and die, regardless of who he'd grow up to be.
She wanted Ben saved, no matter the cost. Sawyer respected and understood how she felt and even though he felt differently, he risked a great deal to bring Ben to the Others so he could be saved. Sawyer did this solely because of how deeply he respected and understood Juliet's needs.
2 Could Have Been With: Miles
Sawyer never showed any romantic or sexual interest in men, but if there was a man he could've been in a relationship with, it would've been Miles. He and Miles worked closely together for three years in the Dharma Initiative and as cops in the flash-sideways.
They became good friends who trusted each other and shared excellent chemistry filled with sarcastic banter. They knew how to work together as a team and could've brought that sense of teamwork, trust, and chemistry to a romantic relationship.
1 Juliet: They Needed Each Other To Move On
Sawyer and Juliet needed each other to move on in the flash-sideways. When they touched, they remembered their lives and the beautiful love they shared. No one else could've helped Sawyer and Juliet remember their lives.
Their remembering and coming back together was a key part of being able to reunite with their friends and move on with the rest of the group in the church.
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