Dan first moved into the neighborhood in 1999 next door to the sisters with his niece, Jenny Gordon, who befriended the sisters the same day. After some time, Dan found himself attracted to Piper, but didn't want to show his affection due to fear of rejection. Piper soon found out and genuinely returned his feelings. Soon they became a couple, though Dan sensed tension whenever Leo Wyatt, her ex-boyfriend, was around. Despite honesty in their relationship, Piper found herself unable to share with Dan the knowledge about her being a witch who often had to fight dark forces.