3 Shades of Blue: Miles Davis, John Coltrane, Bill Evans, and the Lost Empire of Cool by James Kaplan

Your date has been going extremely well: the banter, the chemistry, the moments of simpatico. The date has now seamlessly moved to your place, and you put on something that makes an entrance but does not intrude. Something sensuous but not presumptuous. You want to hear a trumpet breathe, piano cascading like water, modes turning to each other and sounding as nature intended.

You put on Miles Davis’s immortal Kind of Blue. Just as you are taking in Davis’s solo on “So What”—shrugging yet emoting, full of space and attitude yet brimming with taste and emotion, your date tells you that you are among five men in your demographic who have played this album for the same purpose.