Description
After skipping every high school reunion, Maura decides to attend her 40th hoping that one particular classmate will be there.
She has something that she’s wanted to tell him for years: she is sorry. Sorry for what happened to him. Sorry for the abuse he suffered by the priests in their town.
When she finds him at the reunion, they talk. And Maura remembers the moments that shaped her own life: the good, the bad, and what she wore through it all.
Now expanded to three acts, the play follows Maura and Brad beyond the reunion as she asks for his permission to tell their story, and they discover what it means for him to say “yes.”
One high school reunion. Eight life-changing events. Nine memorable outfits.
Team
Colleen Murphy is the playwright of I Wore What When. She writes about health care—executive briefs and PowerPoint presentations—for a living. She is still amazed that she wrote a play that never uses the word “health,” even though, in many ways, it is all about wellbeing.
Colleen is an associate member of The Dramatists Guild of America and a playwriting student at the University of Chicago Graham School. You will find her in Chicago when she is not traveling for work or play. No pun intended.
I Wore What When received the Best Script Award at the United Solo Festival in April 2025.
Michelle Shupe originated the role of Maura in I Wore What When. She is delighted and grateful to have had the opportunity to bring Colleen’s compelling piece to the stage.
Michelle’s selected stage credits include: Milwaukee Repertory Theater (Much Ado About Nothing), Alabama Shakespeare Festival (Our Town, God of Carnage, Romeo and Juliet), Broadway in Chicago (Love, Loss and What I Wore), Goodman Theatre (Pericles), Illinois Shakespeare Festival (A Midsummer Night’s Dream, Richard III and Scapin), and Shakespeare Theatre Company (Macbeth, The Winter’s Tale, Don Carlos, Duchess of Malfi).
Her additional credits include work with Washington Shakespeare Company, where she was a company member, as well as Studio Theater, Signature Theater, and Theater J.
Michelle has received multiple Helen Hayes nominations. She serves as the associate artistic director of The Shakespeare Project of Chicago, where she directs and acts in staged readings throughout Illinois. She is an Actors’ Equity Association member.
Michelle received the Best Actress Award for her performance in I Wore What When at the United Solo Festival in April 2025.
Shole Milos is an actor, movement specialist, choreographer, and director with extensive experience in the theatre community.
Since 1999, he has been an ensemble member of Lifeline Theatre, where he has directed, performed, and choreographed numerous productions.
Shole is a graduate of Loyola University of Chicago with a degree in Theatre and Communications. He is based in Chicago when he’s not enjoying theatre in New York, London, and places afar.
Shole has joined the expanded three-act play as Brad with Michelle Shupe directing.
Performances
I Wore What When was presented as an Equity Approved Showcase at the United Solo Festival on April 5, 2025 at Theatre Row in New York City.
The production received two festival honors:
Best Script – Colleen Murphy
Best Actress – Michelle Shupe
Acknowledgements
I Wore What When was made possible by the encouragement, experience, and generosity of many people and organizations. With gratitude to:
- Doug Post, playwright, composer, lyricist, and instructor
- Colleen’s playwriting classmates at the University of Chicago’s Graham School
- Wendy-Lane and the team at the United Solo Theatre Festival
- Daniel at Foundry Zero
- Richard at Studio Inocencio
- Dominique at Wolford Boutique Chicago
- Anwar on Fiverr
- The Dramatists Guild of America
- Actors’ Equity Association
- Respect Together and Executive Director Yolanda Edrington
- New York City Alliance Against Sexual Assault and Executive Director Emily Miles
- Sellers on eBay!
- Our many family and friends who supported the journey
- And, of course, Michelle & Shole
Contact
Thank you for your interest in I Wore What When. We are available to partner with nonprofit organizations working to prevent sexual assault and support survivors. If your organization is interested in using a performance as a fundraising or awareness-building event, please contact us to explore the possibilities.