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Matt Nathanson – Sunday New York Times Lyrics 7 years ago
I think this one is pretty clear. He had a great relationship and they promised they would stay together. You only stay with someone until you don't. He still misses her and wishes they had kept their promise so he imagines what it would be like to still be with her.

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Matt Nathanson – Sky High Honey Lyrics 7 years ago
I bet you're laughing at some joke he told you
With his arm around your sunburn shoulders
I spent the morning with my face against the window seat
Looking down at all the things that got the best of me

He's clearly a bit jealous of his ex's new person. He's mulling over the regrets he has and what he could have done differently.

No more late night drives to Boston
No more Cure songs to get lost in
No more taxis, subway tokens
Arms wide open, I'm sky high honey - gone

They had some great times but it's over now.

I take the streetcars around San Francisco
Get winks from the pretty boys down in The Castro
Through the turnstiles roll the chappy girls and the shabby dolls
I can't resist myself, I get their names, I never call

He wants to feel loved or wanted again so he's trolling for attention but he's probably still not over his ex so he doesn't even bother with the numbers.

You wait too long, you never leave
And it feels like dying but still your heart beats

Not sure if he's talking about her waiting and not leaving or himself, but clearly he's struggling with the loss and it's painful.

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Matt Nathanson – Answering Machine Lyrics 7 years ago
I definitely think he's in the "rub it in your face stage". He's trying to move on but still really feels for the ex.

I met a new one and she looks just like you
She gives me everything that you didn't want to
And maybe I don't need saving after all
She sticks in my ribs almost better than you did
And maybe I'm tired or maybe she glows

He even found someone that looks like his ex. The problem was he loved her but she didn't treat him right, but somehow he still feels like she would be better for him because his new girl sticks ALMOST better.

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