"I Used to Love H.E.R." is built on an extended metaphor. Common uses the story of an imaginary girl he once loved to talk about the evolution of hip-hop music and culture. And he definitely gets across his message; he thinks hip-hop has taken a few wrong turns. Some of the detours he identifies have to do with the music itself, but a lot of them have to do with how obsessed hip-hop had become, in Common's eyes, with a superficially flashy lifestyle.
Style and image are a huge part of this lifestyle that Common talks about. Style is a way of expressing systems of belief, like Afrocentricity. When Common writes about how the woman in his song trades in her old hairstyle for "braids, beads, and medallions," he's supportive of her showing her beliefs through fashion choices. When hip-hop starts to be all about image without substance, though, Common gets critical: "Stressin' how hardcore and real she is / She was really the realest, before she got into showbiz."
The more attention she pays to the authenticity of her image, the less real she becomes.
Common also sexualizes "H.E.R." in an effort to address the moral corruption that he sees in the mainstream. This is where things get a little more complicated. Common's sexualization of hip-hop works for his metaphor in part because of a sexual double standard. Women are generally afforded less sexual freedom than men by Western society. (We talk a lot about that double standard in our discussion of Beyonce's "Single Ladies.")
Common makes a point by using one of gangsta raps more superficial aspects, hot girls in tight clothes, against it. The lines in "I Used to Love H.E.R." that discuss "H.E.R." sexuality are borderline satirical. Common talks about being attracted to the woman because she's so real and down-to-earth; he says that she's "pure, untampered." Later, as her tastes change and she goes mainstream, he's worried that the number of men she's had sex with has contributed to how she's changed:
I did her, not just to say that I did it
But I'm committed, but so many n----s hit it
That she's just not the same lettin' all these groupies do her
Whoa. The message is clear: Common is saying that he still loves hip-hop enough to make music of his own, but at the same time, he thinks that all the people making sub-par music have watered down the genre. Those people aren't committed to hip-hop culture as a way of life and as a way of bettering the world; they're just cashing in.
And on the surface, Common is talking about a woman being less real and less interesting because she's had sex with too many people, which touches on the objectification of women in gangsta rap. The way he's phrased it, her sexual life is also totally passive, because she's just "lettin' all these groupies do her." Getting his message across relies on his audience judging the woman for the decisions she's made in her sex life.
Imagine if the song were called "I Used to Love H.I.M.," though. Would the sexualized aspect of "H.I.M." work the same way? Could Common portray moral corruption by saying that a male rapper let too many of his female fans sleep with him? What do you think? We're really, genuinely asking, because this is an interesting and important question.
A 2009 interview with the LA Times in which Common discusses his style includes the quote, "Wearing limited-edition pieces or obscure brands 'is almost like having a woman in your life who hasn't been all over town.'" (Source) That last part is a quote from Common himself. This is the same sentiment expressed in "I Used to Love H.E.R."—it's the belief that a woman is more valuable the more exclusive she is.