Part 3 of human vs AI brainstorming experiment

last one I swear

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Here is the third part of my experiment. I wrote a post in mid-2024 which was me in the moment trying to brainstorm my way out of a plot problem. Scouts honor that I was writing that I as I went, ie you are looking at my actual thinking on the page as I tried to solve a major plot problem. I have un-paywalled that post if you’d like to read it in its entirety, but today’s post is written under the assumption that not everyone will do this.

Here is the plot problem from the original post:

So here’s my plot problem: The thematic content of Book 4 has a lot to do with angsty love. Specifically I was thinking of Those Who Leave and Those Who Stay, Elena Ferrante’s second Neopolitan novel, wherein (SPOILER SPOILER) the MC is deeply infatuated with a boy, but she never tells him, and spends a summer with her and her BFF watching the BFF and the boy fall in love with each other and start an affair. The other vibe is from Greta Gerwig’s Little Women, specifically that part where Timothee Chalamet is trying to confess his love to Saoirse Ronan—they’ve been close friends for years—and she’s like, No, no, we promised this was the unspoken thing we would never acknowledge. I really really liked that specific type of angst and wanted it to be a key feature between potential lovebirds in my next book.

But sometimes the readers are clearly going to ship two people, and it’s going to be frustrating that they’re not together, so you need a really good reason that two people who seem like a good match would not be together. Okay, so here, I’m going to brainstorm all the reasons I can think of that two people who would be a good match are not together even though maybe it’s meant to be.

As is typical with brainstorming, the object is to spit out as many things as possible without really thinking about it or judging it. My intent was to first come up with a list, then expound upon the ones that are more interesting.

Let’s get the AI response first.

Prompt: “I would like you to help me with a creative task. I am going to write a book where a key feature is that there is a lot of angst between characters A and B. A and B meet in college and are friends well into their thirties. The angst in the book is that A and B are in love with each other and there is a lot of longing for each other, but they are not together for the entirety of the book. Readers should read the story and really want A and B to be together romantically. However, I need a good reason WHY they are not together, because frequently in stories the obstacles keeping lovers apart are stupid. Can you come up with a list of twenty reasons why two people who would be a good match are not together even though maybe it’s meant to be? Each reason should be no longer than one sentence.”

Response: (the parens is my commentary, I am categorizing)

• One of them is in a long-term, seemingly stable relationship for many years. (LTR)

• They have vastly different life goals or career paths that take them to opposite sides of the world. (career)

• A past misunderstanding or miscommunication created a deep rift in their friendship that hasn't fully healed. (misunderstanding -> deep rift)

• One of them struggles with commitment or fears vulnerability in a romantic relationship. (commitment issues, vulnerability issues)

• Societal or familial pressures strongly discourage a relationship between them. (society, family)

• One of them believes the other is "too good" for them and self-sabotages any romantic potential. (low self esteem sabotages)

• They are both fiercely independent and struggle with the idea of merging their lives. (too independent)

• One of them is dealing with significant personal struggles (e.g., mental health, addiction) that make a relationship feel impossible. (personal struggles)

• They mistake their deep connection for purely platonic love and don't recognize the romantic feelings. (confused about feelings)

• External circumstances, like a major life event or family obligation, prevent them from exploring their feelings. (external circumstances)

• One of them is secretly dealing with a health issue that makes them hesitant to start a serious relationship. (secret health issue)

• They have a strong fear of ruining their cherished friendship if a romantic relationship fails. (don’t want to ruin friendship)

• One of them consistently misinterprets the other's actions and believes their feelings are unrequited. (misinterpretation)

• They both have different ideas about what a romantic relationship should look like. (different understanding of romance)

• One of them prioritizes other aspects of their life, like their career or family, over romantic pursuits. (romance isn’t prioritized)

• They keep missing opportunities or timing is consistently off in their lives. (timing)

• One of them is convinced the other doesn't feel the same way and avoids the topic entirely. (avoidance)

• They belong to different social circles or have fundamentally different lifestyles that seem incompatible. (incompatible lifestyles)

• One of them had a negative past relationship that makes them wary of repeating similar patterns with the other. (bad experience.)

• They both carry unspoken assumptions about the other's desires and expectations in a relationship. (unspoken assumption of what the other wants or expects.

This was my list (today’s commentary in brackets)

1. A likes B, but B doesn’t like A (assume vice versas on all of these). [i meant to say that they like each other but not at the same time] (timing)

2. They both like each other, but think the other doesn’t. (misunderstanding)

3. Timing or other physical impairments (distance, illness) (timing, health issue)

4. A likes B romantically, B like A as a friend, but grows to change their mind. (feelings change)

5. One or the other is in a committed relationship. (LTR)

6. One thinks they are not good enough for the other (self esteem)

7. One thinks they are too good for the other (reverse self esteem)

8. Financial reasons (money)

9. cultural or religious reasons

10. They are only physically attracted but not mentally so it wouldn’t work. (shallow interest)

11. They are mentally attracted but not physically. (only emotional/intellectual interest)

12. It is forbidden/ taboo

13. One is not emotionally prepared for a romantic relationship (personal struggles)

14. One wants a relationship but is distracted with a Bigger Thing. (prioritization)

15. Sexual incompatibility

16. Values incompatibility

17. One needs something from the relationship that the other cannot give (eg, children).

18. One doesn’t want to be happy.

19. One both hates and loves the other. (ambiguous feelings)

I think the AI did a lot better at this than at the book naming task. As you can see there is some overlap between what it said and what I said. What I did not see was what some AI proponents keep insisting they see: some completely outside the box thinking that an intelligent person could not have come up with themselves. What I did in the original blog post is go through all my reasons and expound upon them, ultimately making a judgement if they worked or not. For ones where we overlap, I’m going to show my explanation vs the AI head to head.

Prompt: For the first item on your list, can you expound upon this? this can be anywhere from two sentences to 250 words. You can invent specific scenarios for the characters. But also discuss how this would work in the story.

This is the “one of them is in a relationship one.”

AI: Imagine A meets their partner, Sarah, in their early twenties, perhaps even before or shortly after meeting B in college. Sarah is kind, dependable, and they've built a comfortable life together. Years pass, they establish routines, maybe even buy a home. To the outside world, and even to A, the relationship appears solid and fulfilling. However, beneath the surface, a deeper, more passionate connection with B lingers, a "what if" that simmers quietly.

In the story, this could manifest in several ways. B might witness A's seemingly happy relationship from afar, creating a sense of longing and resignation. Perhaps B dates other people, but no one quite measures up to the unspoken understanding they share with A. Alternatively, the narrative could offer glimpses into A's internal conflict – the comfort and security they find with Sarah versus the undeniable pull they feel towards B. These moments could be subtle, a lingering glance across a crowded room, a shared joke that Sarah doesn't quite understand, or a feeling of profound connection during a late-night phone call with B. This long-term relationship provides a significant and believable obstacle because it's not based on malice or a glaring flaw, but on the inertia of life and a seemingly good, albeit perhaps not soulmate-level, connection. It raises the stakes and makes the reader question whether A will ever risk the stability they've built for the uncertain possibility of a deeper love with B.

My response was a lot shorter, because this was a given: “5: One is in a committed relationship. I already thought this would be in play. One is locked down in a multiyear relationship where they are living together with someone as partners. They start happy, but that decreases over time.” [to expound a little: A rarely dates, nor does she express an interest in B in college, despite being quite infatuated. B, having no idea, goes on with his life and while they are living in different countries, enters into a committed relationship. The relationship becomes really stressed after this partner loses her job and becomes depressed, refusing to look for a job or do pretty much anything. B is torn because he wants to help her, but she refuses help for years, but he also can’t break up with her because he’s afraid of what she’ll do if he does, and he does care about her wellbeing].

I want to show you one of my longest responses, which was for “A likes B, but B doesn’t like A.” You can see that as I was writing it, I was thinking through how this would work and how well it would work.

response: “The standard unrequited love situation. Tried and true. We have a girl who likes a boy, but he doesn’t like her back that way. She thinks of him romantically, but he doesn’t reciprocate. But, given the story, they are friends. In fact, they become very close friends for years. So he does like her as a person. Thinking through the logic here: what are reasons why someone would like someone as a person but not as a potential romantic partner? a) he’s not physically attracted to her b) she might be physically attractive but gives him the ick somehow c) she has some trait that that would be tolerate-able for a friend but not a romantic partner d) some people are friends with people with really different values from them but would not date/marry someone with such different values. In this particular story, A is not true— he does find her attractive, so that won’t work. B) this might work in some sense… not “ick” per se, like he is grossed out by her, but there’s something about her that says “don’t go here.” Something unwelcoming. C) C goes with B a little. I could see him being intrigued by how mysterious and clever this person is, but also finding it a bit scary, like he wouldn’t know how to handle or understand her. I can have a mysterious friend, but when I go home to my partner, I want to feel safe. So maybe she feels safe as a friend, but not as a romantic interest. [so it’s been a year since i wrote the post, and C and B are ultimately what I went with for the story] D) I need to think more about this- I have a sense that a lot of their values are similar. They are liberal college educated people who probably agree on a lot of things. But I think I’ve identified a weak spot here—mainly because I haven’t fully finished working on the characters—but they may have somewhat different worldviews given their different backgrounds (one was born and raised abroad in dangerous circumstances, one is more compassionate to humans in general because of an interest in human rights.) [having since completed my character analysis, I do think they have similar values and this would not be an issue.]

This was my response to the second one: 2: “They both like each other but think the other doesn’t… [so miscommunication, misunderstanding]: This happens a lot in romances, but the problem is, the longer the span of time where they don’t know the truth, the more annoying it is. It can’t be a simple misunderstanding ala “I saw you talking to a hot woman you must be cheating when actually it was your sister.” I was thinking a third party could mislead one or both of them, but now that I’m writing this, I think it can’t be just the third party, [at the conception of the idea for the book, it was ONLY a third party misleading them that kept them apart] but also the characters piecing together that “clue” [ie what the person misleading them told them] with actual real information that could be interpreted as being consistent with that. What happens is that people’s psychology and insecurities stand in the way of them seeing things clearly. I have a greater understanding of the girl’s psychology (she was raised to think she was less-than) but not the male character’s- so I need to work on that. [doing this exercise made it occur to me that I needed to build HOW it was so easy for them each to be misled by the third party. It also made me realize that I had too much of a psychological hole for the male character. ]

I want to show you the AI’s scenario for “They have vastly different life goals or career paths that take them to opposite sides of the world” because I had a few responses of my own that touched on career.

Picture this: A has always dreamed of a quiet life rooted in their hometown, perhaps running the family business or working in a community-focused profession. B, on the other hand, is driven by ambition and a desire to explore the world, maybe pursuing a high-powered career in international business, scientific research in remote locations, or even artistic endeavors that necessitate travel. Their initial connection in college might be intense, built on shared classes, late-night conversations, and a deep understanding of each other's core values.

However, as they graduate and their individual paths diverge, the geographical distance becomes a tangible barrier. Years could pass with occasional emails, video calls across time zones, and fleeting visits that only serve to highlight the chasm growing between their daily realities. A might build a comfortable life in their familiar surroundings, while B experiences the excitement and challenges of a life abroad. The story could emphasize the bittersweet nature of their continued friendship – the joy of reconnecting overshadowed by the awareness that their fundamental life choices keep them apart. This reason feels authentic because it stems from genuine aspirations and the natural trajectory of life pulling people in different directions, making a romantic relationship feel logistically and practically impossible, regardless of their emotional connection. The angst arises from the reader seeing the deep compatibility of their personalities while also understanding the seemingly insurmountable obstacles of their chosen lives.

I touched upon career in a few different responses, so I will put them here:

My response to timing/ distance: “3: I think some of the above [1 and 2] should be combined with physical roadblocks. Timing: one or the other is in a relationship, one ending up in a multi-year relationship that results in pregnancy. But also, these are both jet setters so they are moving around to different cities, so while they maintain a close relationship with looooong emails [the long emails are a huge part of the angst] and seeing each other occasionally, they haven’t had much time post- college to be in the same place at the same time.”

My response to 14: “One wants a relationship but is distracted with a Bigger Thing: Didn’t really think of this till just now, but this is potentially a good one. Both go on to have careers that are important. One is documenting various wars around the world. The other becomes a human rights scholar. The girl would very much start to think that her purpose for being is doing this work, and that it’s silly and pathetic to be distracted by romantic yearning.”

I want to show a “not good enough” comparison because we both had that one.

AI: Imagine A sees B as someone exceptional – perhaps more intelligent, more charismatic, more successful, or even just possessing a certain effortless grace that A feels they lack. This perception, rooted in A's insecurities, creates a fundamental belief that they are somehow unworthy of B's affection. Whenever a romantic opportunity arises, A might unconsciously (or even consciously) undermine it. This could manifest as A becoming overly critical or argumentative with B, pushing them away with self-deprecating humor, or even choosing to pursue less fulfilling relationships because they feel that's all they deserve.

In the narrative, this could play out through A's internal monologue, revealing their deep-seated insecurities and the constant comparison they make between themselves and B. B might express interest or offer subtle romantic cues, but A misinterprets these as platonic affection or politeness, reinforcing their belief that a romantic relationship is unattainable. The angst for the reader comes from witnessing A's self-destructive behavior and recognizing the tragic irony of the situation – the very person they admire and long for is within reach, but A's own flawed self-perception acts as an impenetrable barrier. This reason feels particularly poignant because the obstacle isn't external but internal, highlighting the power of self-doubt to derail even the most promising connections. The reader will likely feel a sense of frustration and a strong desire for A to overcome their insecurities and see themselves as worthy of B's love.

my responses: “4: Someone changes their mind. I think the girl likes him romantically, convinces herself that it will never be and they are just good good friends, then maybe convinces herself that its psychologically unhealthy for her to have this attachment to him. Importantly, the last thing would affect her behavior, like shutting down any potential flirting on her part, and mis-seeing any potential signs from him. Now that I think about it, the way he thinks about her grows and changes over time. He has an initial teenage boy thought: she’s pretty does she like me? But is then kind of scared of her, then grows to have a deep friendship with her that he doesn’t want to lose. Again, I’m missing something about his psyche here that I need to figure out, but it has to do with his childhood. At some point, when he realizes he could lose her [she is missing, assumed dead], he more fully comes out as liking her.

“6: One thinks they are not good enough for the other. This could go both ways. Girl was raised to believe she wasn’t good enough and enters into young adulthood feeling super awkward and uncool. Boy is intimidated by girl not being easy to read, but also intellectually. He thinks, if she likes me, she would have given some sign because this is true for most people.

[Where we are now with the story is that Girl had an extremely rejecting father- as in he left her mother right after she had her, then married a white woman whom he had children with that he dotes on. Girl constantly wants to achieve because she thinks achievements will get her father’s approval. This never happens because he dies when they are on bad terms. She also came from a background where she was one of very few brown people at her school. When she first meets boy, she’s actually in a state of emotional development that is delayed— she’s still in the grade school mode of having crushes on boys—the thought of actually being with one is still a foreign concept. She both cannot see any signals from Boy that he might like her but she also doesn’t want to see them. Because then there is that terrible vulnerability of liking someone! She’s not self destructive, she’s very neat, and the neat boundary around her pushes others out. Boy on the other hand, enters college with a lot of confidence and ease with girls. He also doesn’t sweat the small stuff or have social anxiety because he has been through far worse (he’s a refugee from the Balkans War) which is why he has a very “live every day like its your last” attitude. He puts out feelers to her, and when he gets no response, makes a normal assumption that she’s not interested. By the time his relationship is falling apart, he understands it is not normal to have a female friend you write five page letters to and think about all the time.]

I don’t know if anyone will read this whole thing, but here are my thoughts after doing this:

• In my particular case, I don’t think it was the actual brainstorming—the coming up with the list of 20 items— that was helpful, it was the act of thinking through how each item could work. It was asking myself questions and trying to answer them. Note that answering them was something that builds upon the ultimate underlying architecture of the book: I had to understand things about character and motivation. I had to point out to myself what I already hadn’t seen. In other words, the journey is the destination. You can skip the journey to get to the destination, and then you either still have to do the same work, or you don’t do the work and write something shallow.

• IMHO, there’s a blandness to the scenarios the AI writes that actually reminds me of something you see when you read tons of queries: nothing unexpected, fine, meh. The first scenario the AI wrote feels like when you are reading a query or synopsis for a book that is perfectly blah. There are definitely books out there with blah plotlines but if the whole point of using the AI is to help creativity.. it’s helping you create the equivalent of a boiled chicken sandwich on white bread.

• As with every time querying comes up, I always bring up specificity. “They have careers where they are traveling and are busy all the time, so they can’t be together” = generic “She’s become a public intellectual who has written a book so controversial she routinely gets death threats. Though she remains a humble person, she has become outrageously successful and this ends up being pretty intimidating to men. Because of B’s sometimes-happy go lucky personality, he often thinks people don’t take him seriously, so there’s a mismatch there. He has also spent the past ten years as a war and conflict photographer and between that and his childhood he has some PTSD which kind of means his emotions can be really compartmented”= specific.

• It makes sense to me that people will use AI to do tedious tasks, like categorizing millions of things, or processing routine forms. It doesn’t make sense to me that people will use it to “save time” in creative endeavors. This falls under the philosophy that we should do as much stuff as possible because more hustle = more stuff = more goodness. You can have pho made of broth that has taken two days to make, or you can crumble a packet of seasonings and chemicals into a bowl of hot water. Both are soup.

Will we ever want to watch two robots play tennis with each other? I mean, maybe you’d want to watch to see if the technology of bipedal robots has finally gotten down dexterity in footwork or something, but I don’t think you’d be emotionally invested in the game. People consume art for entertainment, but they are also consuming it because they want to reflect on the human condition, which is something a machine cannot meaningfully do. The best experiences of consuming art is when the artists points something out about humanity, or the world and you think, “my god, that’s right.” A lot of queer people reported that the movie I Saw the TV Glow —a movie I saw and didn’t really get— made them absolutely sob in the theater. There’s the sense of “I feel seen.” I feel seen implies that someone is viewing you. That recognition is coming from another person, a human being. Someone is seeing you, seeing themselves, seeing the world, and trying to make a reflection of this in the fictional world. Art that does not do this is meaningless.