They met a few days after Sakura fell off the ice village and into the demon world. When Hiei picked up on Sakura's ice maiden aura, he followed it; he was born in the ice world himself and that made him want to see who she was. He was being raised by thieves, so he also wanted to see if there were any tear stones he could steal.
When he got there, he saw an older, stronger woman (Rinna, her guardian) with Sakura. He knew better than to attack, sure that Rinna would either beat him if he attacked her, or get revenge if he attacked Sakura. So instead, he waited for Rinna to leave to find food or something. When she left, he took the stone that Sakura had left unprotected.
He made a sound as he escaped, and Sakura woke up and tried to follow him. Being weak and much slower than him, it took her a long time but she found him eventually. She confronted him and just as Hiei got fed up and was about to attack her, Rinna arrived and took Sakura to safety.
But Rinna wasn't all that motherly. She wanted Sakura to have a sense of independence, so she let her confront Hiei whenever she wanted, but stepped in if she was about to get hurt.
After a year or two, Hiei got used to her. As long as she didn't purposely piss him off, he didn't try to hurt her. But he was still his violent self, and Rinna still kept a close watch. The older Hiei and Sakura got, though, the less Rinna had to keep an eye on them. She went back to the ice world eventually. Hiei started to show the closest thing to a civil side that Sakura had ever seen from him, and that sparked her interest in him beyond just trying to get back at him for stealing her stone. Without the ridiculous attempts to attack, he was sarcastic and sometimes even (crudely) funny, and it charmed her.
Around the time when their friendship became stronger and they were old enough to both take care of themselves, the bandits became afraid of Hiei's violence. They feared that he would eventually turn on them, and abandoned him. It was a big blow to Hiei, and it made him try to shut Sakura-- the only person he now had-- out. But Sakura was stubborn and wouldn't let him. Hiei didn't tell her that the thieves left him (in fact, he said that he left them), but she still knew that something was wrong. At first, Hiei was just angry at her persistence. Sakura pushed him too hard one day, and Hiei nailed her arm with his sword. She got really mad, but still refused to leave until Hiei gave her no other choice.
While Sakura was gone, Hiei had thought about what happened along with everything else. He couldn't understand why she was so reluctant to leave him; he'd never wrapped his head around the idea that they were actually friends. But he respected that she didn't run away even when he attacked her. Soon enough, Sakura came back. Hiei didn't attack her again; eventually, he finally realized that he was really a friend to her. Soon enough, he started to appreciate her "Just move on" attitude.
They started to get romantic feelings (but they aren't a couple yet). But when Hiei's own tear stone-- the only reminder he had of his ice maiden mother and sister-- fell into a river after an attacker cut the string of the necklace he wore it on, he set off to find it as well as his mother and sister. He didn't want to tell Sakura why he needed to go to the ice world, so he flatly told her he was leaving and kept her out of it.
After Hiei found what he was looking for, he occasionally contacted Sakura, who had gone into the human world in his absence. She was weak enough to pass through the barrier, which only held back strong demons. Eventually he came to her and they spent time together again. Things got deeper, and they started to fall in love.
They separated again a couple of years later, when Hiei teamed up with another demon to steal three artifacts from the Spirit world and was put on probation. But he was a valuable asset, so the prince of the Spirit World eventually cleared his record for assisting the Spirit detective (the one that protected the human world from demon threats) in his cases.
Hiei warmed up to the detective and the rest of his future team, and they were forced to enter a demon tournament. Hiei had nearly gotten killed; he won with his team, but Sakura still wasn't happy. She saw him almost die at least twice in one tournament, and she didn't want either of them to have to go through that again. She tried to make him stop fighting.
Hiei refused, but Sakura kept pushing him. When Hiei got fed up and demanded to know why she wanted him to stop, Sakura slipped about her feelings for him. Just as he couldn't get his head around the fact that they were friends years ago, he couldn't get that they could be more than that either. He angrily called her a liar and left to be alone. He spent a long time thinking about it, going through why she couldn't have meant it. But when he realized that she really did, he showed her that he felt the same way. But he didn't stop fighting; it was so embedded into him that he couldn't just stop.
When Hiei's probation was lifted, he and Sakura went back to the demon world, where Hiei was much more comfortable. He was a lot less held-back there.
Some time after they first arrived, Sakura found Hiei's necklace while swimming. Since he hadn't told her about his past, she didn't think the necklace meant anything. She kept it because she liked the way it looked, and showed it to Hiei. After getting over the shock, he told her that it was his. This eventually led to him telling her his story.
They became mates a couple of years later, and by the time Sakura got pregnant Hiei had long abandoned his hardcore-fighter lifestyle. They moved into the human world for the safety of their children, and would eventually go back when the kids were strong enough to handle living there.
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