If you read my last column, you may recall that impossible pairings are one of the ways I suggest injecting your Authentic Lens—the way you see the world that nobody else does—into an existing script. Another way to think of impossible pairings is:

“Who is the worst person for the job?”

Asking this question, and using the answer to structure your story, works for any form of dramatic writing. The more impossible the pairing, the harder your character will have to work to get what they want—and the better your script will be.

Let’s look at it in terms of five memorable (some critically acclaimed) TV series.

The Sopranos

Who is the worst person for the job of becoming the next Mafia Boss?

A guy so crippled by his emotions that he’s having panic attacks and blacking out.

A Mafia Boss is supposed to be invincible; the toughest guy in the room. The guy that all the guys below him fear and protect. But Tony Soprano? The guy who keels over in his terrycloth bathrobe while feeding the ducks he’s weirdly obsessed with? Not so much.

We see the dramatic question utilized again in the proposed solution to the panic attack problem:

Who is the worst person to require the help of a therapist?

Someone who can’t tell the truth about who he is, or what he does.

The basis of therapy is rigorous honesty. If you can’t tell the truth, it’s unlikely to help. So, we watch Tony try to work around the honesty thing in service of conquering his larger problem: how to be boss material.

Fleabag (season 2)

Who is the worst person for a sex addict to fall in love with?

Someone who can’t have sex.

When I saw a Catholic Priest in the first scene of the first episode of season two, I knew that it was about to replace Fleabag season 1 as my current pick as a masterpiece of episodic television. Season one was great. But it was a mystery, not an impossible pairing. The impossibility of finding love and sexual fulfillment with a Catholic Priest (who has taken a celibacy vow) took season two to a whole new level. And watching someone do the impossible—or try, at least, until it goes up in flames—is what we all tune in for.

Breaking Bad

Who is the worst person to become a Meth Kingpin?

A loser chemistry teacher with stage four cancer whose brother-in-law is an FBI agent.

This impossible pairing offered up five seasons of dramatic narrative thanks to an ingenious structure right off the bat.

Catastrophe

Who are the worst people to get pregnant together?

Two strangers, who live on different continents, and are both over 40.

Add other tangible factors, such as distance, into the equation and your impossible pairing gets taken to a whole new—and in the case of Catastrophe, comedic—level.

Barry

Who is the worst person to want to be a famous actor?

A hitman who nobody ever knows exists because he’s that successful at his job.

All of these prove the point that asking, “Who is the worst person for the job?” ensures that the central conflict of your story is strong enough to go the distance. And, that even when you solve one facet of the problem, eight others will crop up. Why? Because there is no fast and easy solution. Fast and easy solutions are the enemy of episodic storytelling, and really, any compelling character journey in general. They are dead ends. So when it feels easy, look at where you’re going. If the end isn’t impossible to see from where you start, make it impossible, or change the start. And then the fun is doing the impossible!

Impossible Pairings in Features

You can have impossible pairings in any genre, but let’s talk about one where they are part of the structure: the romantic comedy. I read a lot of rom-coms and yet very few are getting made these days. Rom-com (or Odd Couple) pairings are supposed to be “impossible,” but most of these “impossibilities” are pretty easily overcome. They’re more intellectual than actual, “this person cannot be with that person.” Write the rom-com that actually is impossible—until you, and only you, find a way to break the impossibility—and it will stand apart.

The Big Sick did it.

Who is the worst person to fall in love with a white girl?

An Indian guy who will be disowned by his family if he doesn’t agree to their arranged marriage picks. Then, once that guy decides to stand up to his family:

Who is the worst person for him to be desperate to win back?

A woman in a coma whose parents know the guy broke their daughter’s heart.

Your Homework

1. Set a timer for five minutes and come up with 15 impossible pairings for your genre of choice.

2. Run those pairings by three people and see which ones get the most laughs/excitement/interest or whatever emotion people associate with your genre.

The more it feels like, “that could never happen…” the better your script will be.