You’re such a pretty person, I would like to paint a picture of you naked.

Does this mean "you’ll undress while I get my brushes", or does it mean "strike a pose while I take my clothes off"?

  • I will probably be struck down by the feminist lobby for even attempting to help with this. Your sentence is ungrammatical. To correct it you need to place an 'of' before the 'you'. That means the subject would be naked. It would be ambiguous to say 'I would like to paint a picture of you whilst naked', as that would not be clear as to whether it was artist or subject who was to be naked. An artist wishing to operate naked would have to say 'I...paint a picture of you whilst I'm naked'. – WS2 Apr 1 '14 at 9:13
  • I'm also wondering is this a guaranteed unicorn answer question? No better time than now to ask. – Ronan Apr 1 '14 at 9:14
  • @Ronan Actually, I think adding just 'of' would make it ambiguous as well, though perhaps one meaning is more obvious than the other. – Alicja Z Apr 1 '14 at 9:16
  • 2
    This does remind me of the artist asking the farmer if he could paint his horses - the farmer refusing, saying he liked his horses just the way the were. – oerkelens Apr 1 '14 at 9:40

The intent of the speaker is perfectly clear: it is the subject that is expected to undress. At the same time, the sentence can be construed to be ambiguous, which the debased subject can use to their advantage to gain the upper hand right back. "I would like to paint a picture of you naked!" — "Well, start undressing, then". This kind of retort is a paraprosdokian. You will probably be familiar with famous examples such as "One morning I shot an elephant in my pajamas. How he got in my pajamas, I don't know." Same thing. Works precisely because a) it is theoretically ambiguous, but at the same time b) only one interpretation is actually possible in practice.

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  • This is an excellant answer. I certainly couldn't make an April fool of you. – RoDaSm Apr 1 '14 at 12:15
  • What's not "possible in practice" about painting while naked? – Lightness Races in Orbit Aug 19 '14 at 9:12

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