The Trouble With Jessica

There’s a unique thrill to being dropped into a dinner party where every smile is strained, every compliment doubles as a jab, and civility is hanging on by a thread. That’s exactly the space where The Trouble with Jessica, directed by Matt Winn, thrives, leaning into discomfort, absurdity, and the kind of tension that feels almost too real. It’s a sharply written, darkly hilarious dinner party spiral, where each course is served with a side of existential dread and emotional unraveling.

The setup is simple, in the best way: Sarah (Shirley Henderson) and Tom (Alan Tudyk), a couple on the verge of financial ruin, host a gathering at their soon-to-be-sold house. Enter Jessica (Indira Varma), an uninvited guest whose unexpected actions spark a hilariously grim moral spiral. What follows is a brilliantly twisted unraveling of ethics, ego, and home equity, as the group faces a decision no dinner party should require.

This is exactly the kind of closed-door drama that pulls you in like a fly on the wall. As a viewer, you’re not just watching the night go sideways, you’re in the room. The conversations feel overheard. The tension, suffocating. And the longer it goes on, the more it feels like you’re stuck at the worst social event imaginable, where the wine keeps flowing and the truth keeps spilling.

“…a dinner party where every smile is strained, every compliment doubles as a jab…”

What makes The Trouble with Jessica work so well is that every single character feels both ridiculous and real. They’re not caricatures, they’re people caught in a moral dilemma, armed with egos, regrets, and very British levels of emotional repression, including Kate (Olivia Williams) and Richard (Rufus Sewell). The performances are uniformly excellent, there isn’t a weak link in the cast.

Tonally, the film walks a tight wire between satire and sincerity, and it does so with sharp comedic precision. It’s laugh-out-loud funny, biting, clever, and constantly surprising in how it mines humour from deeply uncomfortable moments. The script crackles with quick wit and awkward tension, every line delivered with the kind of timing that turns passive-aggressive banter into a precision-guided takedown. But the comedy never feels weightless. Beneath the jokes lies something sad and recognizably human: the way people bury their worst instincts under a layer of civility, or disguise self-interest as self-preservation. Some of the strongest moments are also the quietest, when the laughter fades just enough to reveal the loneliness beneath.

The direction by Winn keeps things tight and claustrophobic, without ever feeling stagey. The house itself becomes a kind of emotional pressure cooker, no one can leave, and no one really wants to be there. You can practically feel the air thicken with every passing hour, every failed attempt at control.

And yes, the ending works. It sticks the emotional landing without over-explaining, leaving just enough ambiguity to spark debate. You don’t need full closure when the character arcs are this richly drawn. It’s the kind of ending that lingers and almost dares you to rewatch, just to track every passive glance and sharpened smile you missed the first time.

The Trouble with Jessica is a masterclass in small-scale storytelling. It’s funny, sharp, emotionally layered, and quietly devastating. A dark comedy that earns its darkness and doesn’t flinch from the sad reality that sometimes, the worst decisions are made with the best dinnerware.