In 2008 Boleros for the Disenchanted received its world premiere at Yale Repertory Theatre in New Haven (James Bundy, Artistic Director; Victoria Nolan, Managing Director). It was directed by Henry Godinez. Linda Buchanan was the set designer. Yuri Cataldo was the costume designer. Joe Appelt was the lighting designer. Veronika Vorel was the sound designer. The stage manager was Danielle Federico. The cast was as follows:
| FLORA/EVE | Sona Tatoyan |
| DOÑA MILLA/OLDER FLORA | Adriana Sevan |
| DON FERMÍN/OLDER EUSEBIO | Gary Perez |
| MANUELO/PRIEST | Felix Solis |
| PETRA/MONICA | Lucia Brawley |
| EUSEBIO/OSKAR | Joe Minoso |
In 2009 Boleros for the Disenchanted was produced at American Conservatory Theater in San Francisco (Carey Perloff, Artistic Director; Heather M. Kitchen, Executive Director). It was directed by Carey Perloff. Ralph Funicello was the set designer. Sandra Woodall was the costume designer. Nancy Schertler was the lighting designer. Fabian Obispo was the sound designer and composed original music. Elisa Guthertz was the stage manager. The cast was as follows:
| FLORA/EVE | Lela Loren |
| DOÑA MILLA/OLDER FLORA | Rachel Ticotin |
| DON FERMIN/OLDER EUSEBIO | Robert Beltran |
| MANUELO/OSKAR | Dion Mucciacito |
| PETRA/MONICA | Michele Vazquez |
| EUSEBIO/PRIEST | Drew Cortese |
In 2009 Boleros for the Disenchanted was also produced at the Goodman Theater in Chicago (Robert Falls, Artistic Director; Roche Schulfer, Executive Director). It was directed by Henry Godinez. Linda Buchanan was the set designer. Rachel Anne Healy was the costume designer. Joseph Appelt was the lighting designer. Ray Nardelli and Joshua Horvath were the sound designers. Gustavo Leone was the composer. Alden Vasquez was the production stage manager. The cast was as follows:
| FLORA/EVE | Elizabeth Ledo |
| DOÑA MILLA/OLDER FLORA | Sandra Marquez |
| DON FERMIN/OLDER EUSEBIO | René Rivera |
| MANUELO/PRIEST | Felix Solis |
| PETRA/MONICA | Liza Fernandez |
| EUSEBIO/OSKAR | Joe Minoso |