Their relationship was labeled in the category 'enemies' way before Harry Potter was born. Lord Voldemort stands in the dark side of the war, while Harry stands with the light. Not as if he has a choice anyway.
But something about Voldemort intrigue Harry. Even if he was the enemy. Hagrid and all other people he met praised him for defeating the dark lord. He hated it. Hated something he can't even remember except for a woman's pleas, which turned out to be his mother, and a flash of green light. Some people can't understand that. Others worship him like a god, but fear him all the same.
He had the pleasure of meeting him when he was in first year, in his Professor's head. And even if he wanted to curse the man until his voice grew hoarse, he was still intrigued.
In Harry's second year he met Tom Riddle, a charming young man with a topnotch brain. A favorite to almost everyone except for Dumbledore. His fascination with that man increased. Even if half of the time he was trying to kill Harry.
As he contemplated if having Ginny alive will be more beneficial than having Tom Riddle win in the Chamber of Secrets, he decided he will have both. But in the mean time he had to run because there's a basilisk on the loose.
His third year past by without hearing from Voldemort but it was not less than eventful because of familial issues. Apparently, Sirius Black, the right hand of the man he was fascinated with, betrayer of his parents, escaped and was believed to be headed at Hogwarts. Turns out he was innocent. And oh he successfully casted a Patronus.
Fourth year came slowly. Harry's participation in the Triwizard Tournament made sure his year will be another stressful one. Until he met the snake-like Voldemort. He can't bring himself to feel guilty to be interested in his parents' murderer, and a lot more innocents' and now Cedric's. He wanted to unravel the riddle he calls Voldemort. As he stared into those enchanting ruby eyes that is full of hate and anger, he acted foolishly.
"Lord Voldemort, will you accept me to join you?"
"Well, well, well. Savior of the Wizarding World, turning dark? And why should I believe you?"
"You intrigue me."
Prompt: Intrigue