I’m only dating these men because my uncle bequeathed me money and I need to get married by the end of the year | 2026 MIDSUMMA FESTIVAL

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https://www.theatreworks.org.au/2026/dating-these-men

Date Reviewed: 21/01/2026

With a title that reads less like a name and more like a confession, I’m only dating these men because my uncle bequeathed me money and I need to get married by the end of the year, tells you exactly what kind of show you’re in for.

The musical unfolds as a string of sketch-like encounters that will feel uncomfortably familiar to anyone who has survived the modern dating world. Each “date” is its own miniature disaster, heightened just enough to tip from cringe into comedy. It kicks off memorably with dinner in a car. “Well, I did say you could take me anywhere to dine,” shrugs the nephew, played by Luke Costabile, setting the tone for the litany of men to come: emotionally unavailable, deeply odd, spectacularly unsuitable.

In this small world, Jeanette-with-the-glass-eye, initially a throwaway detail, resurfaces later, reinforcing the show’s cheeky suggestion that in dating, no one ever really disappears. It's a small world they just re-enter your life in stranger contexts.

Hovering over it all is the disembodied voice of the uncle, chiming in from the netherworld like a camp conscience. Urging exploration, risk and chaos, he’s a neat narrative device that gives the show momentum and an emotional anchor, even as the plot gleefully skids from one calamity to the next.

Trent Cliffe, who plays all the supporting characters, is a standout. His vocal work is impressive, his character shifts sharp and legible, and his comedic timing consistently lands. He moves easily between grotesque exaggeration and moments of surprising warmth. Costabile’s Larry grounds the madness amid the mounting desperation.

The musical routines are Disney-sounding playful rather than show-stopping, serving the characters and jokes instead of overpowering them. This is less about leaving the theatre humming and more about recognising yourself, or your worst date, with uncomfortable clarity.

Ultimately, I’m only dating these men because my uncle bequeathed me money and I need to get married by the end of the year is exactly what it promises: funny, absurd, and buoyed by strong performances and a sharp eye for the rituals and humiliations of dating. Beneath the silliness sits a familiar ache, the fear of ending up alone, the pressure to perform romance correctly, and the stubborn hope that after all the disasters, something real might still be possible.

And if nothing else, the title alone deserves applause.

• Just in case you were wondering, the longest title for a theatrical work ever is not this one: The record for the longest title of a play belongs to the 1963 work by German playwright Peter Weiss, which is widely known by the shortened name Marat/Sade. Its full title is The persecution and assassination of Jean-Paul Marat as performed by the inmates of the Asylum of Charenton under the direction of the Marques de Sade. (Try fitting that in an It's on the House review title section). 

Highlights

• A relentless parade of spectacularly bad dates that feel lifted straight from real life 
• Musical numbers that erupt with such enthusiasm you briefly feel like you’ve wandered into a deranged Disney film 
• Trent Cliffe’s chameleonic performance, juggling multiple characters with precision and warmth

Who’s it for?

• Anyone who has dated in the age of apps, situationships and emotional unavailability 
• Fans of sketch comedy, cabaret-style musicals and sharp observational humour 
• Those who enjoy their comedy buoyant, self-aware and just a little bit painful
  

Performed at the Explosives Factory at 7pm nightly through to 23 January.

Reviewed by Mary Sinanidis.