Dennis connects via Zoom with theater director-actor & writer Ryan O'Connor to discuss Ryan's production of Stephen Sondheim's A Little Night Music, which is currently playing at the Greenway Court Theatre in Los Angeles. He talks about the production's long journey to opening night, his casting of trans and non binary actors in major roles, reckoning with the play's period gender dynamics and bring croquet into the mix. Ryan and Dennis also bond over not loving the scripted show's so-called happy ending. Ryan also recalls how his mother and musical theater saved him from relentless bullying when he was an adolescent. He recalls being part of a reality competition Your Own Show: Oprah's Search for the Next TV Star in 2011 and the heartbreak he felt when the show didn't hit and the fame he thought would happen, didn't. Other topics include: that time he was in the same room with Sondheim, spending quality time with Oprah, getting sober, being part of the "rain cover" scenes on Big Little Lies and watching Nicole Kidman have a bite of donut at craft services, working the the late director Jean-Marc Vallee, stumbling out of Lindsay Lohan's SUV and why he loves musicals. And after the interview, Dennis does about five minutes on Jennifer Lopez's fim Marry Me and why too much J Lo is never enough.