Recently I had a debate regarding the following statement, intended to be a compliment:

If I were half as smart as your girlfriend is pretty, I'd rake in millions.

The person who says it, compliments the other guy's girl. Sounds casual and safe, which was my position.

The opposing opinion was that the statement could be offensive to the other guy who may perceive it as a reference to his own intelligence.

I admit, I may be missing something. I need help understanding how this could be misinterpreted.


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