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Caught in the Briars Lyrics

The back alley's full of rain and everything's shining
As holy as she can be, the trick is in the timing
Free as the morning birds, fragile as china
She is stuck in the weakest heart of South Carolina
Where all of the naked boys who lay down beside her
Sing her the saddest song, all caught in the briars

I never meant to fall so hard in her doorway
All of the sinners here have crosses for Sunday
Kissed at the county fair, frisked in the city
Where proof is an answered prayer, but ain't it a pity
That all of the naked boys who lay down beside her
Sing her the saddest song, all caught in the briars
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Cover art for Caught in the Briars lyrics by Iron & Wine

Pretty sure this is about a relationship with a prostitute, and how the man feels shame, but also confides in her, in an attempt so escape life's problems (briars).

"The back alley's full of rain And everything's shining As holy as she can be The trick’s in the timing"

Introduces the woman. However, I hear "The Tricks AND the Timing", which reinforces the idea that she's a prostitute - she knows where and when to turn a trick.

"Free as the morning birds Fragile as china She’s stuck in the weakest heart Of South Carolina"

'Free' in that she probably doesn't have a 9-5 type job, but 'stuck' in that she has fallen into the routine of supporting herself solely by turning tricks in SC.

"Where all of the naked boys who lay down beside her Sing her the saddest song All caught in the briars"

The sad gentlemen that pay for her services also confide in her the hardships of their daily lives.

"I never meant to fall So hard in her doorway And all the sinners here Have crosses for Sunday"

The only verse that's in the first person, this is one of the guys that visits our prostitue. Things are bad for him. His life is hard, and he NEEDS to see this woman. This verse also suggest that the other men "sinners" who go to her are not necessarily lowlife street urchins, but perhaps like him, churchgoers with lives in which they feel trapped.

"Kissed at the county fair Frisked in the city Where proof is an answered prayer But ain't it a pity

That all of the naked boys Who lay down beside her Sing her the saddest song All caught in the briars"

This last passage seems to indicate that perhaps our prostitute ALSO has a 'normal' life outside of her prostitution -- one in which she goes to the county fair with her husband. Maybe she's trying to escape, just as her clients are?

My 2 cents, anyway.

My Interpretation

I'm not sold on the prostitute angle fully, but I'd say the "I never meant--" could be indicative. Though maybe he's talking more about hypocrisy when he says "all the sinners here have crosses for Sunday" in this beautiful way, seeing the warmth in her and not shaming her like some snooty bullshit upperclassman might

 
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