This September, The Blackbird at Gillman Barracks will take on a new role: not just a place for drinks, music and dinner, but the setting for a story about love, loneliness and the people we think we know. From 2 to 13 September, Gateway Arts will stage The Parting Glass, its first immersive, site-specific production, bringing audiences within just a few steps of its characters as they navigate a relationship that is at once tender, funny and quietly heartbreaking. Adapted for Singaporean audiences by theatre-maker Krish Natarajan from British playwright Chris O’Connor’s original script, the play follows Jim and Sarah, gradually revealing the emotional struggles that can remain hidden beneath seemingly ordinary lives.

The story follows Jim, played by Singaporean actor Rishi Vadrevu, the kind of person who is funny, dependable and always ready to show up for his friends. Yet beneath that easygoing exterior, he is carrying something much heavier. The play asks a deceptively simple question: can someone be deeply loved and still feel profoundly alone? Rather than relying on a dramatic crisis or explosive confrontation, The Parting Glass explores the quieter ways emotional distress can unfold, particularly among men who have grown up being told to push through difficulties, stay strong and keep moving. For director and Gateway Arts Artistic Director Samantha Scott-Blackhall, the production is an opportunity to open up conversations about emotions and masculinity, especially in an Asian context where men may find it difficult to articulate what they are going through.

Juliana Kassim Chan plays Sarah, a close presence in Jim’s life who begins to notice what others may overlook. Through her, the play also considers the uncertainty of loving someone who is struggling: how do you recognise when a person is silently asking for help, and what can you do when they cannot explain what they need? It is a question that extends beyond the characters on stage, inviting audiences to think about their own relationships and the people around them. In a city where busy routines can make it easy to assume that friends, colleagues and loved ones are doing fine, the story offers a reminder that emotional struggles are not always visible.

The decision to stage the production at The Blackbird is therefore more than a change of scenery. The bar is where Jim’s friendships, routines and sense of belonging take shape, allowing the audience to step directly into the world they are watching rather than observing it from the traditional distance of a theatre auditorium. That intimacy is central to the experience: as Vadrevu puts it, performing in the space removes a layer of distance and creates the feeling that audiences are sharing the same world as the characters. To make an evening of it, ticket holders will also receive 15% off food and beverages at The Blackbird, which will serve a co-branded speciality drink, “The Parting Glass”, exclusively during the run.

The production also extends beyond the 75-minute performance itself. Gateway Arts is partnering with Eagles Mediation & Counselling Centre (EMCC), following their collaboration on Third Man Syndrome in 2025, with EMCC counsellors present at every post-show discussion. Audiences will have the opportunity to hear from counsellors, mental-health practitioners and people with lived experience, while EMCC will also maintain a front-of-house presence for those who want to learn more about available support.

For those looking for an evening that combines dinner, drinks and something more reflective, The Parting Glass offers a particularly intimate proposition: pull up a chair, step into someone else’s world, and perhaps leave looking a little more closely at the people sitting beside you.

The Parting Glass plays from 2nd to 13th September 2026 at The Blackbird (Gillman Barracks). Tickets and more information available here