Lyric discussion by downsetone 

So, Brendon said in an interview that this song was a sort of sequel to “I Write Sins Not Tragedies”, which is about the best man walking in on the fiancee of the groom on the night before the wedding sleeping with someone else. “The Ballad of Mona Lisa” is from the perspective of the best man, who confessed to the groom that his soon-to-be-wife was sleeping with another man the night before their wedding.

“She paints her fingers with a close precision” She, the ex bride, is worrying about her appearance, because she’s turned into a prostitute, and she’ll lose business if she isn’t kept shiny and clean. “He starts to notice empty bottles of gin” He, the best man, is realizing how much he’s been drinking because he’s wondering if he did the right thing by telling the groom about the bride sleeping with someone else. “And takes a moment to assess the sin she’s paid for” he then starts noticing how she’s dealing with the sin that “she paid for”.

“A lonely speaker in a conversation” they’re talking to each other, but not really. They’re making small talk, and it doesn’t really matter, he doesn’t need her help. “Her words are swimming through his ears again” basically, he’s thinking about what she said to him when she found out that he ratted her out. “There’s nothing wrong with just a taste of what you paid for” she’s a prostitute now, and she looks really tempting, and he’s the one that got her into this mess, so he’s thinking that he’s gonna get to sleep with her, because he turned her into one.

“Say what you mean, tell me I’m right” He’s contradicting himself, first wanting her to let him know did he do the right thing, sleeping with the ex fiancee of his friend? Then he’s thinking, just tell me its okay. “Let the sun rain down on me” he wants the truth, but he’s not sure what it is. “Give me a sign, I want to believe” He wants her to let him know if what he’s done is right, but then (contradicting again) he’s thinking that he wants to believe for himself.

“Whoa, Mona Lisa, you’re guaranteed to run this town, whoa, mona lisa, i’d pay to see you frown” She has him in her grasp, just like she had the groom in her grasp, and the man she slept with. She’s turned into a prostitute and everybody knows it, and they’d “pay to see her frown” because she’s done bad things by sleeping with someone else while about to get married.

“He senses something call it desperation” He’s noticing that she’s running out of things to say, and how to act. “Another dollar another day” So he keeps coming back, mistaking the desperation for need of money and business. “If she had the proper words to say she would tell him that she’s have nothing left to sell him” When in reality, she doesn’t want him coming back. He’s the one that called her out, so she doesn’t want to please him in any form.

“Mona lisa wear me out, pleased to please ya, mona lisa wear me out” He’s saying keep doing him, he doesn’t want to think about if what he’s doing is right or not. He’s pleased to please her, because thats what his instinct is.

“There’s nothing wrong with just a taste of what you paid for” He’s thinking to himself, because he’s the reason she’s a prostitute, that there’s nothing wrong with getting a taste of it. So the song ends on a slightly eerie note, because he doesn’t think what he’s doing is wrong, that its perfectly okay to do it, so he’s more reassuring himself than anybody else.

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