Maria Gripe’s shadow-series consists of four novels written in the 1980s and feature a character who present themselves as both as a girl and a boy. Carolin, also known as Carl has got a mysterious and captivating aura that leaves everybody fascinated and most people enamoured with him/her. Carolin shares many similarities with the 19^th century author Carl Jonas Love Almqvist’s character Tintomara from the novel The Queen’s Tiara (Drottningens juvelsmycke). This essay examines the desire that is aimed at Carolin and explores the queer situations that arises as consequences of his/her cross dressing. I comparatively analyse the desire expressed in the shadow-series and The Queen’s Tiara to find similarities in who is affected by it and where the queer situations occur. The damaging effect of the desire is explored as well. The essay concludes that while most situations can be viewed as both heterosexual and homosexual Gripe uses genres and metaphors that amplify the queerness. Both Carolin and Tintomara are greatly affected by the desire toward them and get hurt because of it. Gripe and Almqvists charismatic androgynous characters bring desire and despair wherever they go, at least as long as they do not conform to society’s norm of gender dichotomy.