Film

The Sure Thing

Name: The Sure Thing
Genre: Comedy, Drama, Romance
Released: 1985
Cast: John Cusack, Daphne Zuniga, Anthony Edwards, Boyd Gaines, Tim Robbins

Romantic comedy
Light-hearted

The Sure Thing is a breezy 1985 romantic comedy about two college students—a slacker and an uptight overachiever—forced together on a cross-country Christmas road trip. It's witty, warm, and genuinely funny about how opposites genuinely do attract. Perfect for anyone who loves character-driven romance that doesn't take itself seriously.

TMDb rating

3.3

Should you watch it?

Watch it if you enjoy odd-couple romantic comedies where the banter does the heavy lifting and the sweetness sneaks up on you under the eighties gloss.

Skip it if the bickering is the main event for long stretches, and if slapstick-leaning teen comedy from the 1980s feels dated to you, its jokes and mood may land flat.

What it asks of you: A brisk ninety-five minutes, mostly on the road, moving between tart exchanges and quieter moments; it asks you to sit with the friction before the warmth arrives.

Not sure? Find tonight's pick in a minute.

If you liked this

Say Anything...1989

Same era, same sensibility: a sweet-hearted romantic comedy with real stakes and a protagonist who's trying to figure out his life. Cusack plays a similar everyman here, and the chemistry crackles.

But It's unapologetically sentimental in places, and if you're allergic to sincerity under the humour, the climax might feel manipulative.

Planes, Trains and Automobiles1987

Another road-trip buddy comedy where two completely different people are stuck together and actually grow to care about each other. Steve Martin and John Candy's chemistry is electric, and it's hilarious without losing heart.

But It's darker and more melancholic than The Sure Thing—less romance, more existential exhaustion. Pacing drags in the middle section.

While You Were Sleeping1995

Romantic comedy that actually earns its emotional payoff through character work rather than just meet-cute logistics. Sandra Bullock is charming in a slightly awkward way, and the movie trusts its own sweetness.

But If you find the premise too contrived (woman falls for man in a coma), the whole film collapses. It's genuinely gentle, which some find boring.

Not sure tonight? Get a pick in a minute, starting from The Sure Thing

The wildcard

Something you would not have found on your own.

Lost in Translation2003

Both films trust that watching two people genuinely connect is more interesting than any contrived plot. Neither rushes the emotional discovery.

Sofia Coppola catches two people—Bill Murray and Scarlett Johansson—in that moment where you realize someone else gets you. No plot to speak of, just connection building quietly. Long shots of Tokyo, minimal dialogue, maximum feeling.

But Glacially paced and almost plotless. If you need things to happen and characters to express their feelings directly, you'll find this maddening and pretentious.

The Breakfast Club1985

Released the same year and captures that exact moment when teen/college movies believed character development actually mattered. Five different archetypes trapped together realizing they're not who they thought.

But Feels incredibly dated in its psychology—the ending especially plays as shallow now. If you've never seen it, the nostalgia won't carry you.

Much Ado About Nothing1993

Joss Whedon's version keeps the sparring-lovers dynamic alive and immediate. Two people who drive each other crazy slowly realizing they're exactly what the other person needs. Witty without being sitcom-cute.

But It's Shakespeare, which means dense language. If you're not already comfortable with the text, you'll spend half the film decoding dialogue.

Splash1984

Tom Hanks in his pre-Forrest phase, playing a regular guy suddenly involved with someone impossible. Romantic, funny, anchored by genuinely likable characters rather than just plot mechanics.

But The premise is silly (mermaid in Manhattan), and the film doesn't always know whether it's a comedy or a romance. Tonal whiplash.

Moonstruck1987

Cher and Nicolas Cage in a romantic comedy that's weird, operatic, and completely confident in its own strangeness. Proves the genre works when characters have actual personality beyond the premise.

But It's quirky in a very specific way—heavy on magical-realism whimsy and Italian-American family chaos. If that doesn't appeal, nothing will land.

My Best Friend's Wedding1997

Julia Roberts and Dermot Mulroney have that same effortless chemistry between people who actually like each other. It's romantic without being saccharine, and genuinely funny about commitment.

But The supporting characters are cartoonish, and the plot hinges on contrivance in places. It's very much a '90s rom-com, which dates faster than you'd expect.

Can't Buy Me Love1987

High school romantic comedy about a geek and a popular girl that actually understands why these people clash—and why they shouldn't. Smart enough to know it's not actually that smart, which is exactly right.

But Dated teen comedy; the gender politics haven't aged well. Pretty thin on character development for anyone but the leads, and even those are archetypal.

It Happened One Night1934

Direct lineal ancestor—The Sure Thing is this template remade for the '80s. Seeing the original shows you exactly what the film was built from.

The actual blueprint for every road-trip romantic comedy ever made. Claudette Colbert and Clark Gable bicker and bond across America, and every beat of chemistry feels earned. Genuinely funny and surprisingly tender.

But Black and white, 1934 pacing, and some attitudes have calcified badly. You're essentially watching film history, not a movie you can forget yourself in.

Fleabag2016

Same core revelation as The Sure Thing, but inverted: what happens when you're finally ready to stop running from connection? It's The Sure Thing's darker, smarter cousin.

Not a rom-com at all—it's a character study that happens to be hilarious and ends up being the truest thing about romantic love on screen in years. Phoebe Waller-Bridge plays someone learning to actually let another person in.

But Structured as comedy but emotionally devastating. If you want the lightness without the weight, this will ambush you. Also only six episodes—not a film.