The eldest son of Sir Sampson Legend, Valentine begins the play in serious trouble: he is deep in debt, and hiding from his creditors, even though he is “a gentleman” (1.20) by birth. Valentine always insists that his spending was only a means of trying to woo Angelica—thus laying the foundations for the central conflict of the play. He also believes that he can win her love even if he is impoverished. Valentine is therefore, as his name suggests, a romantic figure, someone driven by his emotions instead of pragmatism or even rational self-interest. He refuses to address his problems in a practical way and instead engages in defiance and schemes of deception in an attempt to keep his inheritance.

Valentine’s emotion-driven personality leads him to crave affection as the basis for all of his relationships. He argues against Sir Sampson’s harshness by appealing to the notion of “fatherly fondness” (2.262) and decries his father’s “barbarity and unnatural usage” (2.289) when denied forgiveness. He constantly seeks signs of Angelica’s love for him, confused by her seeming indifference. Valentine also craves authenticity more generally, and he sometimes seems disillusioned with the social mores of his high society circles. While feigning madness, he speaks as “Truth” as a means of offering critical commentary on the behavior he sees around him, further aligning himself with authenticity in the face of corruption and deceit (4.