R. Kelly and Aaliyah worked on the record in Chicago during the summer while she was off from school for summer vacation, she would fly to Chicago from Detroit, and they would work on the album. While recording the album the pair spent a lot of time hanging out together by going to arcades and bowling. This would help with the writing process because Kelly would "write the songs that fit her and what kids her age and her friends were talking about". According to Aaliyah "He just spent time with me, trying to see how I thought about things and what people my age think,". When discussing the writing process for the album Aaliyah said "We vibed off of one another, and that’s how the songs was built, He would vibe with me on what the lyrics should be. He’d tell me what to sing, and I’d sing it. That’s how the whole album was done" The duo recorded the first song, "Old School", at the Chicago Recording Company in Chicago, Illinois and it took at least two days to record. Aaliyah loved recording old school because that song "had an Isley Brothers flair” to it. When discussing the recording process for old school Aaliyah said, "At first, I had to get comfortable, but I had been around Robert, so it was cool. Both Robert and I are perfectionists, and if you listen to the music, there is a lot of passion in it.”