The title That Friend immediately suggests a familiar archetype. We all know someone who can turn a quiet evening into an all-night adventure, someone whose enthusiasm is both infectious and exhausting in equal measure. What makes Alex Wall and Will Sterling‘s comedy work so well is that it never settles for the easy joke of simply mocking that person. Instead, it asks a more uncomfortable question: what happens when the friend you’ve spent years tolerating is also forcing you to confront parts of yourself you’d rather ignore?
The film follows Henry (Josh Brener), a man who appears desperate to leave behind the chaos of his younger years. Planning a romantic Palm Springs getaway with his girlfriend Penny (Billie Lourd), Henry is horrified when longtime friend Paul (Harvey Guillén) unexpectedly inserts himself into the trip. What follows is a steadily escalating series of misadventures, misunderstandings and increasingly ridiculous detours that threaten to derail everyone’s plans.
At first glance, Paul seems designed to be the obvious source of the film’s conflict. Guillén throws himself into the role with boundless energy, delivering rapid-fire jokes, physical comedy and an almost supernatural ability to turn minor situations into full-scale disasters. Paul is impulsive, overly enthusiastic and frequently oblivious to social boundaries. Yet Guillén ensures he never becomes merely a punchline. Beneath the chaos is someone desperate to remain connected to the people he loves, even if he lacks the self-awareness to realise how overwhelming he can be.
Just as importantly, the film refuses to let Henry off the hook. Brener is excellent as a man whose frustrations feel entirely understandable but whose behaviour is often less noble than he would like to believe. Henry spends much of the film convincing himself that Paul is the problem, that he’s simply matured beyond the constant antics and unpredictability. But Wall and Sterling gradually reveal a more complicated truth. Henry’s annoyance often masks judgement, and his desire for stability sometimes looks suspiciously like an unwillingness to engage with anything that challenges his carefully curated version of adulthood.
That balance is where That Friend finds its strongest footing. Lesser comedies would have turned Paul into an unbearable nuisance or Henry into an innocent victim. Instead, both characters are flawed, frustrating and recognisably human. You can understand why Henry is annoyed by Paul, but you can also understand why Paul remains such an important part of his life. Their friendship feels messy because real friendships often are.
The supporting cast adds further texture to the film’s increasingly chaotic night. Lourd brings warmth and patience to Penny, while the embarrassment of riches that is the supporting cast – Miles Gutierrez-Riley, Retta, Rose Abdoo – provide memorable comic moments as the story spirals further off course, thanks in large part to (yet another) Paul-centric shenanigan. Some characters feel underused, particularly as the film juggles multiple subplots, but the ensemble consistently keeps the energy high.
While the film’s third act eases back on some of the manic momentum in favour of more emotional revelations, the shift largely pays off. Guillén, in particular, gets the opportunity to explore deeper layers of Paul’s character, lending surprising poignancy to a role that could easily have remained a collection of comic quirks. The emotional beats occasionally arrive a little too neatly, but they give the film a heart that elevates it beyond a simple comedy of escalating disasters.
At its core, That Friend is less interested in deciding who is right than examining how friendships evolve as people grow older. Some people need to loosen their grip on control, while others need to recognise when their behaviour has become unsustainable. The film suggests that neither growth nor friendship is particularly tidy, and that understanding often arrives only after a great deal of frustration.
Fortunately, getting there is consistently funny. Packed with sharp performances, genuine warmth and enough chaotic energy to power several comedies, That Friend proves that even the most exhausting people can make for great company – at least for ninety minutes.
THREE STARS (OUT OF FIVE)
That Friend is screening as part of this year’s Tribeca Film Festival, running between June 3rd and 14th, 2026. For more information on the festival, head to the official site here.
