You’re never gonna guess who I have to train at work today

When Maddey arrives at work and discovers she’s been assigned to train Quiana — the woman her ex-boyfriend left her for — what should be a normal shift quickly spirals into an emotionally charged, painfully awkward, and often hilarious day. As old wounds resurface and new dynamics emerge, Maddey must navigate jealousy, pride, and unexpected connection while her work crush Omari adds fuel to the chaos.

You’re Never Gonna Guess Who I Have to Train at Work Today is a sharp comedy about breakups, comparison, and the quiet courage it takes to stay open when humiliation is the last thing you want.

Cast and Crew

  • Arianna Wellmoney

    as Maddey

  • Jillian A. Smith

    as Quiana

  • Kiamba Doyling

    as Omari

  • Imani Youngblood

    Director

Production History

You’re Never Gonna Guess Who I Have to Train at Work Today
Written by Arianna Wellmoney
Produced by Wellmoney Productions
Directed by Imani Youngblood

The play was presented as part of the Spark Theatre Festival at the Chain Theatre in New York City.

Performance:
• September 27th, 2024 at 7:00 PM — Chain Theatre, NYC

Cast:
Maddey — Arianna Wellmoney
Omari — Kiamba Doyling
Quiana — Jillian Smith

The festival presentation marked the play’s first public staging, introducing audiences to an early development of the work and its blend of heightened comedy, emotional realism, and intimate character dynamics.

Photos by Steven Pisano

Press

Click the icons below to explore press and articles.