Although Finn probably didn’t intend the reference to reveal anything more than the relatively may/december nature of the potential relationship, it’s interesting to note that many Hold Steady songs have wordplay similar to the stuff that Nabokov’s fond of.
Look, for example, at the brilliant and famous first sentence of Lolita:
“Lolita, light of my life, fire of my loins.”
and compare it to some of the lines from Hornets, Hornets, for example:
“that song got scratched into her soul”
They’re also both very fond of referencing their own work (Nabokov shouts out Pale Fire about a million times in Lolita, and the above quotation is obviously from Certain Songs), as well as shouting out other works of fiction—Finn references Nabokov, and Nabokov loves to reference, among others, Proust.
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The Bones Brigade were a successful and popular skateboarding team which released videos in the mid-eighties. Possibly best known for having Tony Hawk as a member. This sets the time period of her late teenage years where part of the album takes place.
On a superficial level, she’s literally going to leave him for whichever drug dealer can get her the highest. See Girls Like Status.
Holly is getting ready to take the leap to faith, but this can only happen after she has found an object of belief which is sufficient. Or, as she puts it, as soon as she finds “whoever’s gonna get me the highest” (i.e. closer to heaven or a divine ideal, as well as who will provide her with drugs). This shows the parallel between drugs and Christianity that the band uses often.