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Saturday, 10 January 2026

I’m Only Dating These Men... explores the messy, funny world of gay love | Midsumma Festival | Theatre Works

In I’m Only Dating These Men Because My Uncle Bequeathed Me Money and I Need to Get Married by the End of the Year (now that's a mouthful!), Larry is a man racing against time to find love - or at least a legal spouse - before an eccentric uncle’s conditions upend his life. The two-man musical turns dating into a hilarious obstacle course, introducing audiences to a parade of absurd, unforgettable characters while exploring what love, partnership, and connection really mean. Creators, Trent Cliffe and Luke Costabile, take us inside the making of the show, from its wild comedic moments to the personal experiences that shaped its heart.

In this musical comedy, dating is treated less like a meet-cute and more like a survival exercise, and for the two creators, that tension between exhilaration and dread is exactly the point. "Dating is both exciting and terrifying," Cliffe says. "I loved meeting new people but it did come with my fair share of weird and whacky encounters. Seeing how different people operate in the world of dating is a rich source of comedy and we wanted to push those themes further."

"It’s a unique kind of period in your life because you’re looking to settle down and it’s vulnerable," Costabile adds. "Each date can be so varied and you don’t know how they will turn out until you sit down with the person."

And while it's a unique period, it's also a universal period. "Nearly everyone has gone through so it makes it really relatable. I think in the world of queer dating there are expectations that we have to navigate, but it opens you up to additional hurt and heartbreak," Cliffe continues.

The pair have known each other for years, and that familiarity shapes how they work together. Their creative process is a constant negotiation between collaboration, instinct, and the occasional disagreement, but it's a space where ideas bounce back and forth until something unexpected clicks. "Luke and I have been friends since we were 13 so we know how each other operates. Luke is amazing at expanding and diving deeper into things and I’m good at telling him when to stop creating Google Docs of notes with no titles and context that we would lose weeks into the writing process and no one would know which is the right document."

"We know each other's strengths and weaknesses but more importantly we know how to communicate without causing the other to meltdown. There is nothing better than getting together and workshopping funny lines and suggestions into a show," Cliffe explains.

"You need strong communication if you’re going to have longevity collaborating with someone. It’s important to trust that you’re working with someone that has the same instinct as you. I couldn’t have asked for a better writing partner," Costabile tells me.

With a story this hectic, the music and lyrics could pull the show in countless directions. For Cliffe, who wrote the music, the task is knowing when a moment truly calls for a song, and making sure that each number adds emotional depth, rather than landing a punchline. "We liked the concept of each date getting a song. It was a challenge to try and convey more than a cheeky song with funny lyrics, so I tried to encapsulate a mood and vibe with the music to help bring the audience into the show. It was fun to produce this style of music; as silly as it is."

"When I was writing the music, I was focused on ensuring the tracks have their own personalities and distinct from each other. Whether it makes you uneasy or hopeful, it's another way to elicit emotions, while still giving the characters something outrageous to say. Having such rich and diverse characters made the lyric process easy and allowed me to tell a story and deliver punchlines and rhymes," he says.

In the show, Larry meets numerous messy, emotionally unavailable dating prospects. The tricky balance for the duo was deciding how much of that chaos came from heightened satire and how much was drawn from real life. "The origin for each date didn’t specifically come from one we’ve had but rather a mix of both," Costabile tells me. "It’s almost like this kernel of a date happens in real life and we turn it into something grotesque like a reverse pearl. A lot comes from small things in our lives like odd stories from friends, including dates Trent and I have been on."

"I would say a lot of it is lived experience turned up to eleven," Cliffe adds. "We wanted to make a show that had truth in it so there are definitely references to memorable dates we've been on and used that in the characters. It’s been great fun to take something real to the extreme." 

Beneath the mayhem, the show asks a more serious question: what does love mean - romance, partnership, friendship, or simply survival? Exploring these themes has prompted them to reflect on their own perceptions of “the one”. "Working on this show made me realise how lucky I am to have such an incredible partner. No wild men with dandruff or emotional unavailability one-night stands," Cliffe laughs.

"While the show is a little zany and the characters are exaggerated, it does paint a picture of the war you have to go through to find someone you are compatible with. It's an interesting feeling to look back and see the random people you had met in your dating adventures."

Chaotic, ridiculous, and unexpectedly heartfelt, I’m Only Dating These Men… turns the rollercoaster of modern dating into a musical spectacle. Get your tickets to find out what happens when love, luck, and family obligations collide.

MIDSUMMA MINUTE – QUICKFIRE FIVE


1. A song I could listen to on repeat forever is
Luke:
Good Luck, Babe! by Chappell Roan
.
Trent: I Want To Break Free by Queen.

2. One object I can’t live without backstage is
Luke:
My water bottle, because I talk so much.
Trent: My water bottle. Because I’m a hydrated king (and my partner would get made at me).

3. My favourite word is
Luke:
Milieu because it sounds so French.
Trent: Husband, but in the thickest New York accent you can muster. Because it make me feel like a rich New York City wife. 
 
4. Something unexpected that brings me joy is
Luke:
The instagram promo  because its the culmination of the years of work on the show.
Trent: This TikTok account of this guy who dresses up these lizards and Crocodiles and turns them into characters.

5. If I could live one day as someone else, it would be
Luke:
Donatella Versace so I could just walk around in sunglasses.
Trent: Someone taller than me. I want to feel the power of being tall.

SHOW DETAILS

Venue: Theatre Works: Explosive Factory, 67 Inkerman St, St Kilda
Season: 19 - 23 Jan | 7pm
Duration: 60 minutes
Tickets: $38 Full | $32 Conc
Bookings: Midsumma Festival

Image credit:
 Tom Noble

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