Origin: Miles arrives at Hurley's barracks to collect Charlotte. Hurley grumbled, "Great. The ship brought us another Sawyer."
Since Then: Hurley escaped the island, but both of them ended up in working for the DHARMA initiative in the 1970s. Hurley discovered Miles's powers, and they compared notes. Hurley encouraged Miles to get in touch with his father. They traveled to the future, where Hurley's growing leadership role amused Miles.
Origin: Miles first saw the Man in Black, in his monster form, when Ben summoned in to fight the mercenaries at the Barracks.
Since Then: Miles later spent three years working for security at the DHARMA Initiative, during which he may well have encountered the monster. Afterward, he saw it again during the Temple massacre. When Hurley soon after suggested talking to "Locke", Miles refused, recalling the destruction he'd seen. He instead joined Richard in seeking to destroy the Man in Black's means of escape. When they seemed about to meet it again, Miles again took off in fear.
Unlike any other of the final main characters on the island, Miles never met the Man in Black in his human form.
Origin: Naomi came to Miles because of his psychic abilities and she told him that her employer, Charles Widmore wanted to use Miles special abilities.
Since Then: Miles acted as though he didn't know Naomi very well on the Island. He talked to her body post-death and learned that she was murdered by Locke. "She was hot and I dug her accent" was the extent of his sentiments for her death.
Origin: Pierre was Miles's father. They lived together on the island, where Pierre took an active role in taking care of his son.
Since Then: Pierre ordered an evacuation soon before the Incident, sending Miles and his wife away. Miles ended up growing up without his father, and Lara misled him about why Pierre was no longer with them. Miles thought Pierre had left them out of indifference and had died somewhere far away.
When Miles returned to the Island, he found himself in 1974 and ran into his father in the line for a meal. He avoided making contact, however, remembering that his father supposedly never cared about him. Hurley later encouraged him to seek out his father. When Miles looked in at Pierre, he saw him lovingly reading to baby Miles, and when he saw Pierre during the evacuation, he realized Pierre sent his family away out of concern, not neglect. Thanks to Hurley, Pierre eventually learned the truth about Miles, but Miles traveled through time soon after, separating the two.
After death, the two shared a good relationship. They remained together while their friends in the church moved on.
Origin: Miles arrived at Sawyer's barracks, seeking to free Charlotte.
Since Then: Sawyer helped Kate to spring Miles and let him see Ben. When they left the barracks, Sawyer, Miles and Claire started towards the beach camp, and Sawyer issued a "restraining order" keeping Miles from Claire. They traveled back in time together, and the worked in DHARMA Initiative security as partners. They traveled to the future, and Miles helped Sawyer bury Juliet and read her last thoughts. They flew off the island together. In their afterlife, they imagined themselves as partners again, this time as Los Angeles cops. Miles there helped Sawyer get over his desires for revenge.