THIS NOVEL DOES NOT EXIST. But if it ever exists, this probably would constitute major spoilers.
I am terrified I might inadvertently commit literary fiction here, so I’ll just say up front I’m aiming for a traditional contemporary romance novel (heterosexual, HEA) but might miss because I suspect it is closer to a bildungsroman, if one of those could be about a class transition as opposed to a becoming-an-adult theme.
Traditional contemporaries suffer from a where’s-the-conflict problem, and I’ve got that problem. I think of the main conflict as values/judgment and the surface conflict as timing/preference. Subtle conflict can get swamped by larger issues, so the two characters are going to be as alike as I can make them otherwise:
They both have a tech degree (computer science, almost certainly), worked in the tech industry (probably PacNW/Seattle specifically, because I know it the best), recently retired (she’s been retired slightly longer, with less money and still works occasionally — kind of the Early Retirement Extreme version), early 30s, stable family of origin/extended family (and not huge either: so basically 1 or 2 siblings each, similar in age, college educated, with families and job, parents living, possibly grandparents living, small number of uncles and aunts, etc), parents have at least some college education (so this isn’t blue collar, altho they may not all be doctors and lawyers), no nutty religions anywhere in sight, no severe mental illness or disability in the closer extended family — these two are probably the nerdiest in their respective clans and they are probably also unusual in that they are both quite money-focused.
The main conflict is that she doesn’t want to move too far from her origins, and he does. She recognized the kind of distortion in her life that would accompany wealth/retirement and did her best to plan for it/step off at a level she was comfortable with. He did not, mostly because he didn’t think it through and he was doing something that other people were telling him he should want to do.
They met originally at a startup that was successful enough for her to retire (at least for Early Retirement Extreme definitions of retirement). They did not arrive at this startup at the beginning, so they have less burnout and less money than some of the earliest participants and they have some appetite for another. He was in a relationship when he was at this company; she was not. They worked together altho not very closely and were friendly, but this isn’t a Identified True Mate On Sight story. Previous to this company, he had internships while in college and then worked at an established company for a couple years, then at a late phase startup that was acquired by a larger company. His previous relationship started in this time frame, and survived his next employer, a startup that he was in on early and failed relatively quickly. He thinks about retiring, but his significant other is opposed (not a fan of the high asset/low run rate life style). He has a startup idea of his own, and some buddies and 3-4 of them put together an app/cloud service (a document indexing service cloud/app/subscription service). However, it takes up all of his time and a fair amount of the money he had from the previously successful startup, and during a rocky period in the middle of it (when the seed money is running out and they are starting the pivot to the corporate facing version of their service), the girlfriend bails out on him.
He has a bad period of wondering if he should have done this at all, thinks about the money he has already sunk into this startup, considers giving up and taking a stable job at a more mature company (he has offers). He talks this over with friends, including Our Heroine and he is surprised that she is not advocating any particular position, but instead poking at him to understand himself better and what he wants. He isn’t really used to this, but decides to double down. He and his buddies experience substantial success post-pivot and are able to sell out to an investment group that keeps them around for 18-24 months of transition.
When the deal is done (but before the transition commitment is complete), he goes out with the partners and a few other friends. He invites Our Heroine as his date for the evening and they (not the crowd, just the Couple) wind up at her place for the night. She makes him breakfast the next day, and seems pleased with the rushed, somewhat drunken previous night, but when he probes for expectations, she indicates she thought this was I Need A Date crossed with Rebound, and is happy to continue as Just Friends. He is simultaneously relieved and disappointed and confused, mostly relieved because there is still a lot to do.
During the transition period, he starts to have more time on his hands. The ex-girlfriend attempts to get back together with him, and there is an extremely unpleasant discussion with her. She makes really good points about how she left because he completely ignored her AND he was doing a lot of yelling (he was _definitely_ a bad boyfriend during this period and arguably verbally abusive). And he should point out how he wanted to quit so he could spend more time with her and she rejected that because she wanted him making more money so he went out and did that (kind of a whiny, passive aggressive thing going on, but basically valid). Conclusion should be along the lines of, he says that while he can understand her perspective, he can’t _trust_ the person that he understands her to be: she’s either too stupid to understand the consequences of her desires (go make me a bunch of money oh look you are a BEAR when you are working that hard) or unreliable during the inevitable down times when engaging in high risk high reward activities. She quite tearfully argues that he can give her both time and money now so why not? Wouldn’t he be offering that deal to any future partner? He says, at least he won’t know going into it with one of them that they’ll dump him in the crunch. He wants/needs at least the hope/illusion that someone loves him enough to stick it out through the hard times.
Over the next period of time, he mopes about the state of his life and relationships. He thinks about Our Heroine during this period, and spends some time with her but is evasive about what is going on in his head, while discussing the situation with the ex- with a married sibling, also his mom (who he discovers absolutely HATED the ex-girlfriend and has been having trouble concealing her glee about how the ex- dumped her son in the crunch), and one or more other friends (whose advice ranges from, give her another chance she’s hot, from the guy who is always being cheated on, to glad you found some spine).
These conversations, in conjunction with a lot of friendly warnings that now that he has so much it will be hard to figure out who wants him for him, cause him to completely freeze on dating. He’s not progressing the relationship with Our Heroine because he doesn’t trust his own judgment/is terrified. She’s not pushing the relationship because she doesn’t really want to be with someone who isn’t enthusiastic enough about her to push.
He’s past an age where he just wants to sleep around, and can’t quite figure out how to solve his dilemma, so he just doesn’t bother. A fair number of people pressure him to start dating again, setting him up with people, introducing him at parties and he resists. Our Heroine is happy to come to his parties and hang out with him in groups, tends to drink less than everyone else, and while she is a lot more available than most of his friends and acquaintances for mid-week activities (maybe they go on a couple day hikes), she doesn’t stay out very late, and her weekends are frequently booked up far in advance, so while they are seeing each other fairly regular and even having regular sex and overnights, the circle of friends is not correctly perceiving what is going on (they see him without her about as often as they seem both of them, and they don’t really believe that all the rest of this mid week stuff is happening). Possible jokes about imaginary girlfriend.
He has been hooked up with a wealth management team, gets a personal trainer and adopts some Active Hobbies (probably mountain biking and/or road biking, dabbling in other things, but I don’t want this guy to be so well put together that he hooks up with an ultimate frisbee team and I don’t want him to be a rock climber either), when he notices he is gaining weight and generally feeling like crap from too much partying. He is also embarrassed by their relative stamina on day hikes and similar.
The wealth management team does some things beyond helping him decide on a stock selling plan and diversification strategy. They get him to put together a will/trust, and hook him up with a real estate agent. He’s okay with doing the will/trust (on screen conversations at least on the phone probably in person with his parents/siblings/etc. in the course of doing this, particularly for living will/medical power of attorney parts). He’s less okay with the real estate agent and stalls for a while, but the agent is persistent and at some point, he has enough time and is sufficiently caught up on other basic needs that he sees a house he absolutely adores and buys it. The agent then attempts to hook him up with an interior decorator, and he acknowledges that the house is crazy empty with just the stuff from his 1 bedroom apartment, but cannot bring himself to make decisions about what to put in the house. He has a gorgeous bedroom picked out by/with the ex-girlfriend, and a kitted out kitchen because he is able to cook, but there’s basically Ikea couch and similar in the sparsely populated living room and nothing in the dining room at all (there’s an eat-in area in the kitchen). He orders up a home theater. He has an amazing game system and buys supportive furniture, and has a bunch of gamers over for messy parties (is this computer gaming, board gaming, poker party, all of the above?). One of his arguments AGAINST buying nice furniture is how trashed the place is after a night of movies, games, cosplay all fueled by kegs, a staffed bar and solo cups.
He attempts to recruit Our Heroine to fill in the empty spots: pick out furniture, deal with caterers, etc. She balks. She isn’t particularly interested in the hassle, which pulls him up short, because he had gotten the impression that this was something that All Women Wanted/Did or at least did when they were coupled up, and he can tell from her life that she is quite capable of it. When she declines, he points out that he knows she has helped other people buy sofas etc. She points out that he has referrals to interior decorator etc. which he has declined. He’s trying to get this done for free, and while setting up a household is fun, the scale of this is kind of huge, he is not at all clear about what he wants and he tends to argue with her suggestions (she asserts that people would drink less and behave better in a well-furnished space and he doesn’t believe her, focusing on the greater potential for damages).
She is willing to go out on at least some dates, spend the night, text and call casually on a mostly daily basis, but doesn’t pressure for any commitment or change her FB relationship status (“it’s complicated”, which it has been the entire time he has known her, and he has known about other people she has dated and stopped dating through that time frame). He can’t figure out what any of this means. He also sees himself as low-priority for weekend scheduling, and they talk about why that happens (he is one of her newer friends — most of her friends have been part of her life for a decade or more; he tends not to schedule as far out as most of the rest of her social circle does, so he loses to prior commitments) and come up with some workarounds (we will spend these Friday or Saturday nights as a couple, regardless, and if that means with her friends or with his friends due to later commitments, that is okay).
Heavy handed moralizing here by the author: up through the slightly more mature and ultimately successful startup job, Our Heroinel and Our Hero were quite similar. However, her decision to “retire” caused her to go through a Now What/What is the Good Life/Time to Grow Up process that he did not go through because he was immersed in an extremely time consuming startup that had a lead role in. Now that he has pulled back from the day-to-day/retired himself, he is going through a process she has mostly completed. They are different in several key ways: the above obvs, but also he is substantially wealthier than she is and he has had a taste of wheeling/dealing/hustling that she never has. Her life, world and perspective are drastically simplified by having fewer options and clearer priorities, so while he is overwhelmed by choice and uncertain how to make those choices, she is decisive and has a ton of spare capacity to spend on thinking about how other people do things/what other people are currently thinking and feeling. He would _love_ to have someone take over a lot of this, and figures she’s a great choice for it (she’s already done it once and knows how). She figures that if he’s gonna outsource it, he should pay professionals, but she also thinks he should work through the process himself because that’s what she did. Ultimately, he will need to figure out what his own priorities are (the important part of the process) and then outsource selectively/consciously (not just: live my life for me).
As his transition period is winding up, she is asked by a former co-worker (of both of them) to help out on a niche app/cloud service that he has been working on. It is supposed to be a 6 month commitment, but it goes long. (The service is a bunch of drastically simplified accounting and report generation software, combined with contact management, calendar management, and some pieces oriented towards making event planning and security management work better — that part is probably mostly a ticket system. And the whole thing has extremely heavy security and is sold as part of an extremely expensive subscription service, with the intention of replacing bespoke software and off-the-shelf business software used by household staff of the uber rich. I haven’t decided if the project is the work of one or more tech billionaires who got disgusted with what was available and treated it as a potentially money-making sideline — sort of like Corbis was for Bill Gates and art). One of the higher level people in the group developing the service is a loyalty hire by the/a person/people funding the project and is not very competent. Our Heroine winds up spending a fair amount of time trying to get the requirements and priorities better defined and a reasonable schedule assembled and communicated above/around the problematic person. She is well-compensated, but happy to leave after somewhere between 6 months and a year.
Our Hero is frustrated at her months of unavailability right when he’s got a ton of time on his hand, but he doesn’t dump her, partly because he doesn’t want to be a hypocrite, partly because it is a defined time commitment. But he also sort of thinks, why the hell are you bothering to do this when the payoff won’t be that good and it wasn’t your idea and so forth. Our Heroine’s explanation is because if she turns out to have miscalculated on how much money she needs to live on/she makes disastrous investment errors, this is the kind of gig she wants to take so she can work part of the time and not work part of the time. Also, dude, let’s not lose track of how much a few hundred thousand means to me, just because it means very little to you.
Meanwhile, because she’s just not around and he needs something to do with himself, he turns the house into a Project and just GTDs the whole thing. This actually can combine with the debate about how much a million is worth, when they look at how much she made and how much he spent during the same period of time.
When her gig is done, and his house is furnished, she’s feeling exhausted and relieved to be done working for a while, at the same time she’s got a ton of offers because she Rescued a Near Disaster. They decide they actually get along really well, despite the values differences and the sex is good at least when they’ve been getting enough sleep. He mostly comes around to her way of thinking (keep taking jobs part of the time and not working part of the time) and she decides she’s prepared to participate in his more expensive lifestyle, as long as he doesn’t force her run rate up.
Something like the end, possibly with babies.
I’m still debating about whether I want to flip the genders (make her be the one who overshoots on the lifestyle and then freaks out). But fundamentally, I really want her to be the smart one, so I think not.