In 2006, he and Lee Hae-young co-wrote and co-directed the coming-of-age film "Like a Virgin", in which Ryu Deok-hwan played an overweight trans woman teenager who idolizes Madonna and joins the high school ssireum team, hoping to use the prize money, if they win the national tournament, for sex change surgery. The filmmakers gained praise for their directorial debut and its sensitive portrayal of a potentially controversial subject, which resulted in several nominations and awards, including Best New Director(s) at the 7th Busan Film Critics Awards, Best Screenplay and Best New Director(s) at the 27th Blue Dragon Film Awards, Best New Director(s) at the 5th Korean Film Awards, and Best Screenplay at the 43rd Baeksang Arts Awards. "Like a Virgin" was also invited to international film festivals, including the Generation section of the 57th Berlin International Film Festival, and the 20th Singapore International Film Festival where it won the NETPAC Award.