While growing up every person has at least one interminably uncool relative. The daggy uncle duded up in chest-high jeans. The aunty who distributes socks and hankies every year for Christmas. The father who sneaks in the occasional cheeky shandy.

There are few things more transparently uncool, more kill-me-now-or-we’ll-all-die-from-embarrassment, then a perennial dag pretending they’re still trendy, still in tune with the yoof of today — as if the word “discotheque” never went out of fashion and they never snapped up that Michael Buble CD.

Imagine if that relative were handed a few million dollars to write and direct a romantic comedy about hip young people falling in love, in a plight to prove they’re still ‘connected’. Imagine the potentially ghastly consequences.

Now you have the vaguest glimmer of what it’s like to sit through Any Questions For Ben?, the third feature film from director Rob Sitch and beloved Australian production company Working Dog, who have made precisely that: a dog.

The blobs of writers’ block offal masquerading as a storyline concern 27-year-old Ben (Josh Lawson), a hot shot well-sexed advertising executive who arrives at the epiphany that his life is as vacuous as the film that bears his name. He likes short term relationships with long-legged women; quick stints in high paying jobs.

The dawn of realisation occurs when Ben is invited back to his old high school to speak alongside successful alumni such as savvy international aid worker Alex (Rachael Taylor). After an awkward, scattered speech about billboards and rebranding Ben is the only participant — gasp! — not be asked a question by the students.

He takes this personally; so personally it lands him in a quasi-existential who-am-I funk. Ben asks for advice and gets sub-par responses from his materialistic mentor Sam (Lachy Hulme) and mates Andy (Christian Clark) and Nick (Snowtown’s Daniel Henshall). What does he do to change his ways? He does what he’s always done: chases skirt, and an awkward to-and-fro romance between him and the up market Alex slowly comes to fruition.

The second act is supposed to be about how Ben looks for answers in the wrong places – by dating a tennis star, for example, and going on holiday to New Zealand – but essentially the screenplay (written by Sitch, Santo Cilauro and Tom Gleisner) doesn’t have one. With an almost complete absence of character trajectory, Ben reflects on his life, decides it ain’t right, but barely passes that initial point of realisation. Expect a feast of rom-com clichés, nary an original thought in sight, to fill out the plot: an unfulfilling desk job, a wedding, a visit to a popular sports event, drives in a fast car, an overseas vacation, an airport scene, a hot air balloon, a work Christmas party, a boat trip…

The implausible relationship between Ben and Alex is written and acted with cat strangling caricature, as bogusly applied as the too-bright lipstick decorating star Josh Lawson’s lips (The Dawson’s Creek syndrome). Alex is painted in bleeding obvious strokes as a dignified person worthy of our respect – she’s a member of the UN and she’s, like, met the Prime Minister and stuff – yet the script unceremoniously flings her around, presenting her as low hanging fruit for Ben to nibble on when the time is convenient while insultingly maintaining the illusion that her character amounts to more than that. There is no emotional connection between the two leads, and certainly no fizz between Lawson and Rachael Taylor, though both try their darndest to work the material.

Even the crucial set up scene — not a difficult one to pull off — badly misfires. When Ben talks on stage at the all important alumni event he blabbers and stammers, barely one coherent sentence emerging from his lipstick painted lips. Surprise surprise, nobody asks him a question. How much better that scene might have resonated if Ben had the gift of the gab, silkily verbose and sell-ice-to-eskimos convincing, feeding into his persona as a slick advertising man. And yet the kids still care not a jot, enforcing the idea that’s it’s Ben’s life that’s uninteresting rather than his public speaking abilities. That his existence, while shiny on the outside, is hollow at its core, which is supposedly what this mangled mess of film is all about.

Before a preview screening two weeks prior to its release, Rob Sitch addressed an enthusiastic crowd, describing the city of Melbourne as a key character. Remembering those comments after wallowing in the wreckage of Any Questions For Ben? provides a sobering reminder that Sitch – whose last feature was the pleasant-enough The Dish in 2000 – is not a practicing filmmaker and far from a natural hand at the medium.

Evoking a sense of place requires a great deal more than sweeping helicopter shots of the CBD and a choice of popular locations to film (in this case the Yarra River, the Sydney Myer Music Bowl, Rod Laver arena and others). Unassisted by editors Stuart Morley and Phil Simon, Sitch appears to have no idea how to play with spatial properties, to hold the frame, to allow locations to seep off the screen, to make a city a personality in itself. Cities portrayed in films like  Guys and Dolls (1955), Play Time (1967), Wake in Fright (1971), Collateral (2004) and The Lincoln Lawyer (2011) provide telling reminders that it’s a great deal easier to say these things than to achieve them.

Adding to the overarching feeling that pervades the production – that this graceless comedy has been made by middle-aged dags trying and failing to capture the mannerisms and lifestyles of people decades their junior – is a face-palm soundtrack stuffed to the gills with top 50 bubblegum pop tracks that used to be sort-of cool in mainstream circles three or four years ago. During virtually every moment of visual exposition, no matter how fleeting or inconsequential, Sitch cranks the songs up to ten, giving the film a throbbing brick-to-the-face rhythm that will inspire audio palettes not attuned to homogenized gunk want to bolt for the exit.

Even more painful than Stephan Elliott’s dire A Few Best Men, Any Questions for Ben? is a culture cringe clunker so awfully written and directed it challenges audiences to do the previously unthinkable: to reflect on Working Dog’s The Castle, a prize possession in the pool room of great Australian comedies, in the context of a brilliant fluke.

Any Question for Ben?’s Australian theatrical release date: February 9, 2012.