Kierkegaard amou Regine Olsen. Assaltado por dúvidas se seria um bom marido ou se seria possível conciliar o seu trabalho, a sua fé com este amor, Kierkegaard termina o noivado e engana Regine, tentando criar nela uma péssima reputação de si próprio de forma a que o sofrimento de Regine fosse menor:

Kierkegaard seems to have genuinely loved Regine but was unable to reconcile the prospect of marriage with his vocation as a writer and his passionate and introspective Christianity. Regine was shattered by his rejection of her, and was unwilling to accept Kierkegaard’s breaking of their engagement. Kierkegaard attempted to quell this through actions which made it appear that he didn’t care for her at all; as he later wrote, “there was nothing else for me to do but to venture to the uttermost, to support her, if possible, by means of deception, to do everything to repel her from me in order to rekindle her pride.” He wrote her cold, calculated letters in order to make it seem that he didn’t love her anymore, but Regine clinged to the hope that they would get back together, desperately pleading to him to take her back. On October 11, 1841, Kierkegaard met with her and again broke off the engagement in person. Her father tried to persuade him to reconsider after assessing his Regine’s desperate condition, claiming that “It will be the death of her; she is in total despair.” Kierkegaard returned the next day and spoke with Regine. To her query as to whether he would ever marry, Kierkegaard icily responded: “Well, yes, in ten years, when I have begun to simmer down and I need a lusty young miss to rejuvenate me.” In reality, Kierkegaard had no such plans, and would remain a celibate bachelor for the rest of his life.

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