He attended New York University's Tisch School of the Arts where he studied film.
At this time he met Anna Boden on the set of a student film and, after he finished his thesis short film Struggle, they began dating and decided to collaborate.
So it's frustrating for him and he's slipped in to a bit of a chauvinistic rut, easily swayed by any perceivable new hope he can get his hands on but rarely using it in a new way.
Each of them, reluctantly compelled to play out their role in the game of love and life in order to maintain the balance.
Fleck and Boden have since co-written and co-directed the 2008 film Sugar, which premiered at the 2008 Sundance Film Festival, about a 19-year-old Dominican who immigrates to the United States to play minor league baseball.