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"?
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.