Gustav Wyneken was born to a Christian family, and studied Theology and Philology in Berlin. In 1900 he married Luise Margaretha Dammermann, from whom he was divorced in 1910. From 1900 to 1906 he worked as a teacher in boarding schools, where he was a colleague of Hermann Lietz.
Wyneken coined two influential terms:
The first term was "pedagogic eros", the name given to erotic attraction and/or love between a teacher and a pupil. Pedagogic eros (or Pädagogischer Eros in German) was embodied as a set of concepts popularised by Wyneken's Wickersdorf Free School Community in Germany, and based around the Ancient Greek Platonic 'Ladder of Beauty' model of same-sex pedagogic relationships, but blended with high Germanic philosophical ideas. Although focused on same-sex relationships, his ideas could also be applied to heterosexuality. He led the wider Free School (or Freie Schulgemeinde in German) movement, a movement that founded boarding schools across Germany.
The second term was "Jugendkultur"; this implied that wherever possible adults should refrain from overtly 'leading' youth groups, and older youths should instead lead younger youths. This was part of his deep influence on the German Youth Movement; notably the Jugendkulturbewegung, the Wandervogel and the Adolf Brand's Gemeinschaft der Eigenen. Although it should be noted that he downplayed the then-popular notions of the need for a restored Volkish German culture, and was not known to be anti-semitic. His Free Schools accepted a large portion of Jewish pupils. In a sense, by coining and encouraging 'Jugendkultur' he was the founder of what would later become widely known as 'youth culture'.
Wyneken also influenced Jewish youth movements in Poland and Vienna (such as Hashomer Hatzair), and had some influence on the early Kibbutz education in Israel. He also known to have influenced: the circle around Stefan George; Bruno Bettelheim; and Pier Paolo Pasolini's school in Casara and his Pasolini's later teaching.
Wyneken had himself been influenced by the thinking of Martin Buber and Hermann Lietz; thinking that arises from the Hebrew educational tradition, in which a good education is founded on a teacher's love for his students.
In the maelstrom of ideas and ideologies that was pre-war Germany, inevitably his strong ideas caused much controversy.
The young Walter Benjamin's political aesthetics were greatly influenced by a stay (1905-1907) at a Wyneken boarding school (Haubinda in Thüringen) where he became close to Wyneken. He was also influenced by the Wyneken-edited radical youth journal Der Anfang ('The Beginning'). However, when Gustav Wyneken gave a broadly pro-war speech in Munich in November 1914, the pacifist Benjamin reluctantly broke with his mentor.
It is uncertain what Wyneken did in the thirty years between 1934 and his death in 1964, although it seems he stayed in Germany and tried to be involved with education. His prosecution for 'immorality' (he had allegedly embraced two pupils while naked) under the notorious anti-homosexual Paragraph 175 in 1921 means that it is unlikely that he was involved with the Nazi Party.