When Kanye was first starting out, he was still dating his high school girlfriend, Sumeke Rainey. Her father was the one who gifted Kanye with a box of Marvin Gaye, Curtis Mayfield, and Aretha Franklin records, which he later sampled on his 2004 debut album, College Dropout. It's actually Sumeke's voice you hear on the song "Get Em High" when a girl asks Kanye if he knows Kweli. In "Never Let Me Down," he raps about the promise he made to her father on his deathbed that he'd eventually marry her: "Nothing sad as that day my girl's father passed away / So I promised to Mr. Rainey I'm gonna marry your daughter."
Their relationship didn't last, and he hinted at the reason on Late Registration's "Touch the Sky." "Sure enough, I sent the plane tickets / But when she came to kick it, things became different," he raps. "Any girl I cheated on, sheets I skeeted on / Couldn't keep it at home, thought I needed a Nia Long." The exact date of their breakup is unclear, but it was likely sometime around the late '90s.