It's amazing how dating and courtship have changed through technology. I'm not referring to the evolution within ritual (mixtape to cd compilation to mp3 playlist), but that new rituals like the playlist exchange and facebook status update now exist at all.
Before computers, someone would be wooed through conversation, witty letters, and mementos. There wasn't an equivalent to bundling up and preparing such a big part of yourself and then handing it over. There wasn't anything quite like the Facebook status update to immediately reveal how serious things were or weren't. It happened over time as news spread and you took your boy/girlfriend home to meet the parents.
"the cassette mixtape served a more significant purpose for the relationship-obsessed: an important and often scary stage in courtship. The analog audio equivalent of "pinning" or "going steady," the creation of a mixtape meant things were getting serious (for at least one of the people involved, anyway)." (From Mixtape As Courtship Ritual: A Case Study)
A quick search on dating and mixtapes shows all types of tutorials and tips, but growing up we didn't need the help. It was important to start off with something peppy, putting the best tracks around 3 or 4 then dropping it off a bit, picking it up on 7, and ending slow-- to recreate the curve we'd heard again and again on tapes and cds. You'd make sure to include a variety of tracks that would showcase the scope of your diverse tastes and personality. Throw in a couple romantic songs that express what you had been too afraid to say in person.