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Wealth or material assets play a vital role in a post-industrial society. Literature and culture have never failed to depict this change in society. Both Jane Austen’s Pride and Prejudice and E. L. James’s Fifty Shades of Grey successfully explore the role of material assets in making a man desirable. In Pride and Prejudice, Darcy—“selfish and overbearing”—resembles Grey, who is also “selfish” and “dominant.” In keeping with the genteel tradition of the nineteenth century, Darcy’s courtship of Elizabeth is “gentlemanly” till the very end of the novel as he woos her through a subtle show of his wealth. On the other hand, Grey, displays no such restraint while courting Anastasia; in fact, he even threatens her. However, both Elizabeth and Anastasia ignore the follies present in Darcy and Grey respectively. Money plays a pivotal role in the development of the plots of the two novels. Both Darcy and Grey who are unattainable, rich bachelors of their times, make Elizabeth and Anastasia develop a passion for them, with their behaviour, power and assets. This paper aims to evaluate the role of the different forms of capital, as classified by Pierre Bourdieu and argues that other than the rich male protagonists’ dynamic characters, the capital they possess enables them to woo these two women. In addition, this paper will also argue that E. L. James shaped the character of Grey in such a way that Grey appears to be the modern Darcy.