According to the theory of complementary needs, an upper-class man who is shy would most likely be attracted to:

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The theory of complementary needs suggests that individuals are attracted to those who have traits that complement their own. An upper-class man who is shy would likely be attracted to an outgoing upper-class woman, as her outgoing nature complements his shyness, and their similar social class provides common ground.

According to the Theory of Complementary Needs, an Upper-Class Man