Henry has been through a lot for someone who is still so young. The loss of his parents was by far the worst of the tragedies he's had to deal with. When things seemed to keep getting worse where he lived, he felt it was time for a change of scenery. It was time to start over.
Henry ran away to Japan and was staying with a old friend of his fathers. It was here that his whole life would be changed forever. He was taught martial arts, became friends with Hikari Yagami, introduced to the Digital World and became an enemy of the Digidestined. Like Ken, he was manipulated by Arukenimon. To make sure that she would always be in control of him, she used her Spirit Needle Thread ability on him, turning him into one of her servants. Through secret means she was able to obtain the Crest of Darkness and gave it to Henry, along with a D-3 and D-Terminal. The last item received from Arukenimon was a black Digi-egg which Wolfmon was born from. With these items, Henry would do what Ken had failed to do.
Henry and Wolfmon had become a very strong opponent against the Digidestined. They both served Arukenimon to the greatest of their abilities. Wolfmon though, who truly cared about Henry and hated fighting the other Digimon wished to free Henry and himself from the chains that bound them to Arukenimon. One day while secretly meeting with Hikari and Gatomon, Wolfmon explained to Hikari that Henry was secretly in love with her. How he cared about her so much for being the first and only one from school to open up to him and offer him friendship. After hearing that, Hikari promised Wolfmon that she would do whatever she could to help them out. Hikari had taken what she learned from Wolfmon and told the others just about everything. Henry's feelings for her, she felt it was something that needn't be discussed. Deep down inside, her feelings for him had grown. Hanging out with him all those times after school, learning about the loss of his parents and hearing how to him, life just seemed to be one sad, lonely path.She wanted him to see how beautiful life can be when you find someone to share it with. She would find a way to free him and Wolfmon, with or without the help of the others.
(So this pretty much sums up how they met. I have the rest of the story saved but it's something that I cherish very much since I was a kid. Guess I'm just not ready to share it yet. That or I just can't handle the criticism I'll get lol. Anyways, if you read this, I hope you enjoyed it.)