The Dicks storytelling drill: pick any category of life experience that has multiple instances (kisses, jobs, road trips, fights with siblings, conversations with strangers, embarrassing moments at parties). Ask someone — yourself, a friend, a first date, a storytelling-workshop group — to tell you four stories from that category: the first, the last, the best, and the worst. The four-prompt structure generates immediate story-content without preparation because the prompts activate specific memorable life-events.1
The game has several uses:
First dates — The four-prompt structure generates instant conversation that bypasses small-talk and produces the kind of intimate self-disclosure that builds relational connection in compressed time. Both people learn substantial autobiographical material about each other in the time it would otherwise take to discuss the weather.
Improvisation training — Storytellers in training can use the four-prompt structure to practice telling stories without preparation. The prompts force real-time storytelling under conditions similar to performance pressure, building the muscle of structured improvisation that the remember-not-memorize discipline requires.
Group warm-ups — Storytelling workshop leaders can use the four-prompt structure to warm up groups before formal storytelling exercises. The structure produces immediate stories from every participant, lowering the barrier to subsequent participation.
Self-archaeology — Individual storytellers can use the four-prompt structure on themselves to surface memorable life-events they may have forgotten. The structure functions as a memory-activation tool that generates raw material for homework-for-life processing.
The game has three components.
1. The category must contain multiple instances. Categories with only one instance (your wedding day) do not work; the prompts collapse to a single story. Categories with many instances (kisses, jobs, road trips) generate four-story output because the prompts pull from different positions in the population.
2. The four prompts (first, last, best, worst) target distinct memorable moments. The first targets the initiating experience that established the category in the person's life. The last targets the most recent experience, often vivid because of recency. The best targets the peak experience, often vivid because of emotional intensity. The worst targets the trough experience, often vivid because of negative emotional intensity. The four prompts collectively pull stories from different regions of the person's autobiographical memory.
3. The game produces immediate output regardless of preparation. The prompts are designed so that anyone can answer them without rehearsal. The first-kiss story is in everyone's memory who has had multiple kisses; same with last, best, worst. The immediate-output property is what makes the game useful in time-pressured contexts.
The cognitive mechanism: open questions (tell me a story) overwhelm the responder because they have no constraints on what to select from. The responder freezes, considers and rejects multiple candidates, and produces something tepid out of decision-fatigue.
Constrained questions (tell me your first kiss story) bypass the selection problem by pre-selecting the story-candidate. The responder does not have to decide which story to tell; the prompt has decided. The cognitive load drops; the response emerges quickly; the story is typically better than an open-question response would have been because the prompt selected for memorable rather than random.
The four-prompt set extends this — by combining four constraint-prompts, the game extracts a richer story-set than a single constraint-prompt would. The four prompts together produce a biographical sketch of the person's relationship to the category that no single open-question could elicit.
A second mechanism: the four prompts produce natural-narrative-arc responses. The first and last prompts establish temporal-endpoints; the best and worst establish evaluative-endpoints. Together they sketch a small narrative arc across the person's history with the category. The arc emerges from the prompt-structure even when the responder does not consciously construct it.
The game is one specific deployment of homework for life at compressed scale. Homework for life directs daily attention to the storyteller's life for raw material; the first-last-best-worst game does the same operation across a single category in a single sitting. Both are mechanisms for activating autobiographical memory in service of storytelling.
It pairs with five anecdotes always in pocket: the five-anecdotes discipline maintains a small reserve of pre-developed stories for use in conversation; the first-last-best-worst game generates raw material that can be developed into pocket-anecdotes through subsequent processing.
It connects to storyteller self-centered in a positive way: the game requires the storyteller to focus attention on their own autobiographical archive. The focus is part of the licit self-attention Dicks endorses as the upstream discipline for storytelling-craft development.
You want to use the game in a specific context. The deployment varies slightly by context.
On a first date. You suggest the game playfully. Let's play a quick game — tell me your first kiss, your last kiss, your best kiss, and your worst kiss. Your date responds; the four stories emerge over several minutes. You reciprocate when invited. By the end of the four-prompt exchange, you each know substantial autobiographical material about the other. The conversational momentum continues from there.
In a workshop. You ask participants to find a partner. You give them a category (jobs, road trips, embarrassing-school-moments). Each partner tells the other their four stories. The room fills with simultaneous storytelling. After fifteen minutes, you re-gather and ask a few participants to share with the full room. The room is now warmed up; subsequent formal exercises proceed more easily.
On yourself. You sit down with a notebook. You pick a category from your own life — first jobs, road trips, weddings attended, fights with parents. You write your four stories. The act of writing surfaces memorable material; some of the stories become future storytelling-craft material.
Your first date is uncomfortable when you suggest it. Some people are not in the mood for the game, especially in formal first-date contexts. The fix is to abandon the game if it does not land naturally, rather than pushing it.
The category does not produce four distinct stories. Categories that produce only one or two stories were poorly chosen. The fix is to switch to a category with more instances.
The game becomes a quiz rather than a conversation. If you are asking the four prompts without sharing your own, the dynamic becomes interrogation. The fix is to reciprocate — each prompt asked is also a prompt you answer.
Look at what the four-prompt structure does: it bypasses selection paralysis in autobiographical retrieval by pre-selecting the story-candidates. Several other domains use analogous constraint-techniques.
Therapy / intake assessment frameworks: Clinical intake assessments use constraint-prompts (describe a typical day for you; tell me about your most stable relationship; tell me about your most volatile relationship) to extract autobiographical content efficiently. The structural parallel to the first-last-best-worst game is precise — constraint-prompts elicit richer content faster than open prompts. Therapy tradition has refined the constraint-prompt methodology across decades; storytelling tradition can borrow specific clinical-intake protocols as advanced versions of the four-prompt game.
Journalism / interview protocols: Skilled journalists use constraint-prompts (walk me through your worst day at the company; tell me about the moment you decided to leave; what was the conversation with your boss the day you got promoted) to extract specific narrative content from interviewees. The constraint-prompt methodology is one of the most-refined skills in journalism. Pairing journalism's interview tradition with storytelling-craft: journalism has developed prompt-libraries for extracting specific story-types; storytellers can productively study journalism interview techniques as deeper versions of the four-prompt game.
First-date / relationship-research questionnaires: Researcher Arthur Aron's 36 Questions to Fall in Love uses constraint-prompts of escalating intimacy to accelerate relational connection between strangers. The structural mechanism is the same as the first-last-best-worst game's first-date deployment — constraint-prompts bypass small-talk and produce the intimate autobiographical disclosure that builds connection. The Aron questionnaire has substantial empirical support for accelerating relationship formation; storytellers can deploy versions of the questionnaire as extended forms of the four-prompt game.
The Sharpest Implication The game implies that most contexts where people fail to tell good stories are not failures of storytelling-ability but failures of prompt-structure. People who claim I'm not a good storyteller often produce good stories the moment they receive a constrained prompt. The implication is that storytelling-pedagogy should include prompt-design training — teaching storytellers to construct prompts (for themselves, for groups, for first dates) that produce the conditions for good stories rather than waiting for stories to emerge from un-prompted opportunities.
Generative Questions