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In Samuel Richardson’s sentimental, epistolary novels Pamela, Clarissa, and Sir Charles Grandison, bonds and embarrassment constitute currencies of commerce and sociability. Since sociability is a framework of compulsory social and financial obligation, bondmanship, including suretyship, becomes a metaphor for the perils of reciprocal exchange, social and commercial. In Richardson’s fiction, the social effects of exchanges of literal or figurative bonds or sureties play a role in an economy of embarrassment that also forms part of an economy of sentiment. Circulating letters become the sentimental equivalents of bonds, while bonds embody the sociability of exchange much as letters do. Still, a close reading of Richardson’s handling of the metaphor of the bond as embarrassment suggests an evolution away from the two-party arrangement in Pamela, and towards the more sophisticated three-party suretyship figuratively deployed by Sir Charles against Lady Beauchamp: the impersonal efficiency of the bondmanship by which he brokers her humiliation resembles the operation of an eighteenth-century securities market.