From the album Wishbone Deluxe
This song pretends to be about whether he's brave enough to reach out. It's not. He already knows he wants contact. The real terror is whether they want to hear from him at all. The whole 'do I dare' framing is a cover for 'do you even care I exist anymore.'
They say a clean cut heals the quickest / December to May was spick and spotless
He's trying to convince himself the healing worked. The phrasing gives him away. 'Spick and spotless' sounds like scrubbing a crime scene, not moving on.
You're still the very first name I'd like to reach to tell / 'Cause only you'd find it funny
The wound isn't closed at all. Seven months later and they're still the person he wants to share stupid moments with. That 'still' does all the work.
I saw a wren fly at a window / And if I befriend you, will I crash in magnificent blur?
He watches a bird smash into glass and sees himself. The question isn't really about friendship. It's about whether getting close again means certain death. He already thinks it does.
Do you want to hear from me? / Holdin' back the words that we never say
This is the actual question he's been avoiding the whole song. Not 'am I brave enough' but 'do you want me back.' The shift from 'I' to 'we' means he's still thinking in terms of a shared existence they both refuse to name.
So do I wait by the phone, every day, lonely, or
The sentence cuts off before he finishes the thought. He can't even say the alternative out loud because the alternative is calling, risking rejection, and proving the bird metaphor right.
The whole song circles one unasked question. Not whether he's brave. Whether they'd pick up. The repetition of 'do I dare' is him stalling because the real answer terrifies him. He'd rather stay lonely by the phone than risk finding out they've moved on.