Big List of Relationship Questions

What is this list and why?

In the summer of 2021, I was watching the show "Chuck" . Somewhere in the show, I believe that there is a stack of books titled something along the lines of "101 conversations before I do". 18 or so months later, this specific and yet somehow vague memory pops back into my mind. So I decided to look for that book. I found a book called 101 questions to ask before you get engaged, and made a quick note of the questions in there.
There is also this list of 36 questions that lead to love , which a friend had introduced me to. The idea behind this list is that these questions help two people get to know each other quickly and in a manner that leads them to get invested in the other person.
Clearly, by this point in time I'm fascinated by the idea of having a comprehensive list of questions that one should have answers to before getting married. I don't actually believe one could know everything they need to before getting married. Nor am I personally too very concerned about it. But the general idea of learning some "critical" things about one's significant other seems interesting. Independent of the goal of checking for red flags or compatibility, I think it's a romantic and potentially fun, long drawn exercise.
After reading the book that I stumbled upon, I realised that my list of questions would be fairly different. For one thing, I believe that my girlfriend and I have already had a lot of the conversations that were suggested. For another, some of the questions felt irrelevant to me, as I'm not as religious (or specifically American-Christian) as the author of the book. Finally, there are a few questions that I would want to ask, which aren't covered in the book. So, I figured that it might be a fun exercise for me to:

1. Structure and devise my own list of questions to ask /conversations to have with your significant other before getting engaged / married / committed in anyway
2. Have these conversations with my girlfriend over a few months and use this as a fun process of growing closer to each other

What I am arriving at instead

As I started going through the exercise of structuring my thoughts and putting together a framework for all of my questions, I was arriving at more than I set out to achieve. The objective that I was going after seemed to expand on its own. At this stage, I'm sort of aiming for a few month/year long exercise to take big strides towards developing, enjoying and maintaining my relationship in the long run. My objective is sort of best described in the rough note I made below.

For starters, rather than just a long list of questions / conversations, I intend to also define a few useful activities that will help me and my girlfriend get to know each other better and grow into each other nicely. I also would like to define some sustainable systems which help us function well as a single unit. The hope is that these 3 things together, will help strengthen the foundation for a great relationship going forward. The below note might help clarify how I see these 3 activities as strengthening the foundation of my relationship.

Key conversations

As a natural next step, I tried to further structure each of these 3 steps. I started off with conversations to arrive at a more granular answer of what sort of conversations need to be had. The first breakdown is into conversations about each other's past, present and future.

I like to think of understanding someone's story or their past as a very long drawn and rich story. The story spans years, which may be broken into phases of life. Those phases might be a few weeks or a few years long. But the more granular, detailed and rich, the better, I think.
In any given phase, I would like to understand the external experiences that they have had with events and the people involved. I would also like to understand how it is all shaping who they are as a person.

Understanding how one is developing as a person is a super subjective and difficult idea to breakdown. But I think there are a few useful directions to think in, in order to often develop a useful view of who the other person was through a certain phase. Understanding the predominant emotions and feelings that they felt then is always a great starting point. What one cares about, what their beliefs and values are, what their world view is, what their own view of themselves is, are all useful questions to ask. With such subjective questions, just asking out loud isn't likely to be enough. One would probably have to try to understand these things more subtly, and truly care about developing this understanding about the other person.

Stories about specific stand out events are always fun to hear about the other person. And even early into a relationship, the most significant ones have already come out. However, I think it's useful to have a structure to ask for and gather the details of even the less stand out events. I think that all the small events put together can often be as or more powerful than just the most memorable ones. In any case, I would love to here as many different stories from the life of my girlfriend.
I really like the idea of using the 5 senses to sometime immerse myself in the sound, smell and general feeling of a situation.

In theory, going through all of the events of someone's life should give you the same experience that they have had. But this is obviously far from the realistic outcome. So, another useful dimensions to focus on are the key relationships that they have built. Broadly, one might want to understand the stories that they share with people who are important to them, how they visualise them, what their dynamic is and so on.

Having covered a lot of questions about one's past, the present and future are a little quicker and easier to go through. While the past influences who we are today, it is always good to spell out your own identity, beliefs and behaviour. I have tried to list out some key dimensions of who we are on a daily basis in our lives. I think that it helps to discuss each of these dimensions, or to just observe them all. But one should aim to understand the other persons preferences / tastes as well as the habits and behaviour that they showcase.

While one will likely learn more about their partner's present self through observation, a lot can be learnt about the future only through deliberate discussion. At a top level, it helps to break the future down into some key phases of life that each person imagines life to contain. This in itself will give you some information about the other person's view of the future. Within each phase it helps to go into a lot of detail in terms of how the other person imagines life to be. Specifically what does their dream scenario look like, vs what do they really expect life to be like and why.
To put the phase of life in better perspective, it might help to highlight the key milestones and goals that one has from that phase of life.

To capture enough detail and get key conversations flowing about future day to day life it helps to break the conversation down, and ensure that all important dimensions are discussed. Reusing the structure to understand the present day version of each other is useful here. One likely won't go into as much detail for each individual phase. And rather than understanding preferences and habits, it is more useful to use the dimensions to paint a picture of the expected / ideal day to day life in that phase.
More important than just the picture of day to day life are the responsibilities that come with it. I have tried to put together a structure to address how each person views the responsibilities, and how we may as a unit go about working on them.

The final set of questions to discuss are the key goals that each person sees in life, or in each phase. Maslow's hierarchy is a useful structure to ensure that different types of goals are captured in each phase, without glossing over things which might be fundamental. For each key goal, a structure similar to the one used for responsibilities will be useful in discussing how we can work towards the goal as a unit.

Activities to grow together

The hope is that by this point of time both people have a damn good understanding of who the other person is. Most of the content on how we can get to know each other is covered in the conversations section. The idea behind activities overlaps with this a bit. After all, conversations and talk only go so far. Through activities, observation and living life together one learns things that mere words just can't cover.
But in my mind the key idea behind activities is to ensure that this process isn't just a test of who the other person is. Activities are a way to have a lot of fun with each other. They're an opportunity to experience each other's company in the fullest.
So I have tried to structure activities in line with the life that each person said that they imagine. The idea here is that all of the fun things that you would want to be a part of your day, week, month, year etc are things that you should definitely do with each other. I personally like the idea of making a bucket list of activities that we can go through together. This allows both people to select the kinds of things that they look forward to and want the other person to be a part of. The more fun and whimsical the list, the more fun each of the activities will be. The idea behind reusing those structures is that we could have a super comprehensive list.
Along with all of the plain fun activities, there is room for some activities with more of an ulterior motive. In my mind, it makes sense to also simulate some parts of what life together will be like. This can be fun like a vacation, or a big step like moving in together (which can also be fun). The idea behind these is to also pay attention to how responsibilities and tougher aspects of the relationship play out.

Systems to sustain

Through conversations and activities, the hope is that we would be able to grow together and develop a deep understanding and love for the person that we want to spend our lives with. I expect that this process would uncover a lot, and provide a lot to think about too. So, in order to close the loop a bit, I think it's worth addressing some potentially open points.
Across everything discussed and experienced, there are probably certain things which could provide scope for conflict. At an extreme, might be a red flag. I think it makes sense to note some of these conflict points down through the process. This isn't to tally and take a data driven call on whether to be with the person. The purpose is to try and address potnetial conflicts or come up with systems to work through them. I have tried to structure the types of systems one might want to come up with for different types of potential conflict.
Of course, I also think that it's good to talk through what one might do when all of these systems fail.

That is pretty much my entire structure for a nice big exercise for two people to grow from 2 ones into a single two.