The song is about (and by) an outwardly facile woman coming to terms with her innate sentimentality about and for people she has lost throughout her life in varying aspects- friendship, family and love:
-FRIENDSHIP: Her childhood best friend Gwen Carter, who had turned into a "silly pest" after nearly fourteen years of inseparable friendship; she forced herself to cry the day Gwen and her family moved away.
-FAMILY: Her doting and overbearing grandmother; she admits her advice was wise, but decided she just didn't want to hear it; overwhelmed by her depression, she didn't cry at all when her grandmother died.
-LOVE: An ex-boyfriend or husband who, while he satisfied her sexually, was seen as unmannerly with a crude sense of humor. Complaints from her friends convinced her that she deserved more, someone less strident and more adaptable to her lifestyle.
In all of these situations, after each person departed from her life- and after venting the depression she acquired from each of them, her sentimentality would assert itself as she found she missed them "more than I'd ever have guessed"
The song is about (and by) an outwardly facile woman coming to terms with her innate sentimentality about and for people she has lost throughout her life in varying aspects- friendship, family and love:
-FRIENDSHIP: Her childhood best friend Gwen Carter, who had turned into a "silly pest" after nearly fourteen years of inseparable friendship; she forced herself to cry the day Gwen and her family moved away.
-FAMILY: Her doting and overbearing grandmother; she admits her advice was wise, but decided she just didn't want to hear it; overwhelmed by her depression, she didn't cry at all when her grandmother died.
-LOVE: An ex-boyfriend or husband who, while he satisfied her sexually, was seen as unmannerly with a crude sense of humor. Complaints from her friends convinced her that she deserved more, someone less strident and more adaptable to her lifestyle.
In all of these situations, after each person departed from her life- and after venting the depression she acquired from each of them, her sentimentality would assert itself as she found she missed them "more than I'd ever have guessed"
[Edit: minor changes and reiteration of context]