The elegiac “First Night” serves as the emotional centerpiece of Boys and Girls in America. Craig Finn frequently employs a character named Holly in his songs and this is her first official appearance on this album. Holly was born Halleluiah but her life started a downward spiral after the first time she got high. You can ready about her progress at that link. Looking for information about Holly led me to the The Hold Stead Wiki which provides a little additional information about this song.
Finn draws an interesting contrast between Holly’s Christianity and her drug use on this track. On the one hand, she “cries when she tells us about Jesus.” On the other hand:
Unhinged and uncontrollable
‘Cause we can’t get as high as we got
On that first night
She’s stuck between – not stations – but a desire to give herself back to Jesus and her need to get high. At the start of the song, she’s in the hospital. By the end, she’s longing to get back to the original high from her first night. The narrator’s love (?) for her isn’t enough – its the drugs she loves (which puts a sad spin on the lyric “on that first night/she slept like she’d never been scared”).
I appreciate how in his three major references to Holly, Finn makes a point of using “sound alike” words. Holly is “in the hospital,” “insatiable,” “still looks incredible,” and is “inconsolable.”
The song makes a musical shift about 2/3 of the way through to an anthemic return to the “boys and girls in America” refrain before resolving lyrically with:
don’t bother talking to the guys with the hot soft eyes.
you know they’re already taken.
Don’t even speak to all those sequencer beats boys.
when they kiss they spit white noise.
The suggesting I’m reading from this is that the good guys are taken and the rest are not worth Holly’s time. She’s living in a world where she will never be satisfied. Indeed, as Sal Paradise said, boys and girls in America have such a sad time together.