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Fall Out Boy – Headfirst Slide Into Cooperstown on a Bad Bet Lyrics 14 years ago
Firstly, I've listened to this song well over a thousand times and I still know as much about the meaning as I did when I first heard it.
Here as my best guess as to what it may be about:

Mr. Sandman showing his beam
When he walks into the room the walls lean in to listen
Surfed out brain waves flick back and forth
Like old headlights sniffing model glue again

Mr.Sandman introduces himself in the first verse an ideal man or "the perfect guy" (as asap4now said) and is the speaker for the rest of the song.

Head like a steel trap
Wish I didn't I didn't I didn't I didn't I didn't I didn't I didn't
I don't just want to be a footnote in someone else's happiness

The speaker is in love with a married woman and because of this, he knows that he can never play a bigger role in her life.

Does your husband know the way that
the sunshine gleams from your wedding band?

He is also saying that he is better for her than the husband because he is a "prefect guy" who appreciates and admires her more.

Does he know the way
Does he know the way
Of the crickets that would convince me to call it a night?
But I will never end up like him
Behind my back I already am
Keep a calendar, this way you will always know

The last time you came through
Oh darling I know what you're going through
The last time you came through
Oh darling
Oh darling
Oh darling...

This part of the song suggests that the speaker is in a relationship with someone else, and that by seeing each other, both the speaker and the woman are cheating on their partners (the woman doesn't know this), hence "I know what you're going through". The speaker is also going through a period of reflection and self conflict, almost as if he is looking in a mirror and thinking to himself "Am I really good enough for her?" "Of the crickets that would convince me to call it a night" is probably the speaker's way of saying: "of all the people in the world, only you could convince me to break up with my current partner." This suggests that the speaker has a strong obsession for this woman.


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