This article focuses on imaginative childhood games and fictional playmates in Baltic German children’s games, as seen in the context of, and in relation to, Baltic German domestic and educational culture. Through reminiscing about these games, a view of the Baltic German domestic environment in all its diversity is opened up. It gives an insight into the mental environment – relationships within the immediate and extended family and domestic circle (which also included servants) and the relationships and interactions beyond, but also shares information about the physical environment – the everyday culture and way of life. And in the midst of it all, of course, the narrators are looking back on their own formative experiences and years. The examples of more or less imaginative games are drawn from the memoirs of nine Baltic German authors, of which one text is available in Estonian translation, while the others are unknown to the Estonian reader as complete texts, and therefore perhaps all the more interesting. The authors have been selected from the corpus of Baltic German memoir texts collected from reading, based on the focus of this article, i.e., texts that also deal with the author’s childhood and where fictional playmates and worlds are also discussed. The selection is certainly not exhaustive, but it provides a preliminary insight into the subject. Baltic German memoir literature, especially concerning the generations whose childhoods passed during a period of stability and peace – whether at the end of the 19th century before Russification, or the pre-World War I era – often exhibits a particular contrast. Childhood and youth were left behind at a time when the world was still in order, when the life as it used to be had not collapsed. Later Baltic Germans very often wrote memoirs with their descendants in mind, in order to create a generational link, to introduce the lost world and way of life, but also to generalise the impact of historical events from the individual level to the national group as a whole. Post-World War II memory work directed at descendants became particularly significant, as everything had once again and irreversibly gone. The examples of imaginative childhood games and fictional playmates in the Baltic German memoirs discussed in this article carry a positive tone, occasionally accompanied by a light-hearted and wise reflection. Children were encouraged to engage in independent play, while not being neglected, especially the younger children, for whom the presence of an ‘interested adult’ in the background was noticeable. Storytelling and literature played a key role in the development of imagination and creativity. The plots of literary works were transferred to games and further developed, and dramatization techniques were employed using readily available resources. In addition to classical and romantic literature, the physical environment – buildings, interiors, the surrounding nature – also exerted important influence. Fictional companions existed both in the case of an only child and in the case of children growing up among siblings. In the latter case, there were often shared fantasy characters and worlds – whether they were just air or on paper. Adults also became part of the imaginary worlds and retained their role as interested observers – as long as the imaginary world did not overflow too much – leaving room for individual originality, which has been considered a distinctive feature of Baltic German society. The authors recall their childhood with fond memories, where home and family formed a stable, secure and vital growing environment, and the necessary resilience and resourcefulness for coping with life’s challenges. As such, these examples also fit into the framework of what Helene Hoerschelmann calls “old-school Baltic German upbringing”. Undoubtedly, the self-aware adaptability acquired during their childhood and youth served them well – the successive pivotal historical events, wars and revolutions became an inevitable part of their lives. Thus, a study of the history of the Baltic Germans’ childhood and upbringing could be of interest not only as part of an unknown or forgotten and lost world, but also as a multifaceted source of reflection and comparison, especially from today’s perspective.