In the preface, Trevor Noah insists that he has no regret for anything he has done, but plenty of “regret for the things I didn’t do.” People should fear regret, not failure and rejection, which are at least answers to the questions regret always leaves open.
This short introduction recalls Trevor’s commentary about his feelings on burning down the white family’s house; just as taking responsibility and moving on is a better way to deal with failure than wallowing in pain and regret, being willing to accept failure is a better way to deal with uncertainty than wallowing in indecision and guaranteeing regret for oneself. Indeed, as Patricia’s attitude proves so saliently, approaching decisions with a willingness to take responsibility and/or fail can prevent people from feeling apprehension or fear in the first place.
Trevor is an ugly high schooler, with horrible acne, no money for a haircut, and, thanks to his mother, clothes three sizes too big that he never grows into. He quickly learns that “cool guys get girls, and funny guys get to hang out with the cool guys with their girls.” He would “upset the natural order of things” if he tries anything.
Although he manages to be one of the “funny guys” despite his outsider status and self-proclaimed hideousness, Trevor feels that he should continue to fall in line with other people’s romantic expectations and be grateful for his middling place in the hierarchy (somewhat like colored people were expected to feel grateful under apartheid for not being black).
Trevor becomes friends with Johanna, who is popular, and her beautiful but shy friend Zaheera. He always makes them laugh and develops “the hugest crush on Zaheera,” so he crafts a “foolproof” plan: he will become her best friend and, after three years, she will realize that he is "the guy I was supposed to be with all along," like in the movies. She confides in him about other boys and they start talking on the phone every day after school. And then, at the beginning of the next term, she abruptly immigrates to the United States—and Johanna tells Trevor that Zaheera had “such a huge crush on you.” Trevor feels “three successive waves of heartbreak” and a profound regret at never asking Zaheera out.
In fact, Trevor’s foolproof plan works perfectly, but he is so convinced that he will fail that he never tries to talk to her about his feelings. If Fufi taught him that love is not possession and Maylene taught him about how social expectations govern relationships and where he stands in the school hierarchy, then Zaheera teaches him both the virtues of honesty even when he expects failure and the ultimate unreliability of the same romantic expectations and scripts he learned about on Valentine’s Day.