Throughout the novel, Will helps Annie understand that the key to successful dating is displaying confidence and individuality. Annie seeks a “new woman” transformation like what Dick does to Jo in Funny Face, but Will has “never met anyone like her before—and it would be a damn shame for her to morph into some popular social construct of what a woman should be like on dates” (65). He already believes she’s worthy of attention and attraction as she is and intends to coax out the personality she’s spent her entire life tucking away.

In the first chapter, Annie almost backs out of her date because she is “a person who avoids attention at all costs” and can barely stomach being the sole focus of one man for the night (3). During the date, Annie can’t even manage to talk about flowers—which are the focus of her job—due to self-consciousness and shame, evidencing her extreme lack of self-confidence. In contrast, Will wows Annie on their first interaction of the novel, and she wonders what “it would be like to date a man like him? All charisma and confidence” (17). Though she has yet to discover that confidence and individuality are the keys to mutual attraction, Annie immediately takes notice of how these exact qualities stand out in Will.