Lots of good input, and food for thought! SO and I have never had issues regarding money, primarily because everything is separate. We've been together 7+ years. But this is a good point:
What still bothers me, as someone who never married in part due to financial imbalance issues, is how you do anything but joint finances in a logistical sense. OP for example says she has retirement savings, no kids, other sound habits. When she marries someone, "in sickness and in health, for richer and for poorer" how do you decide how to split the costs, mortgage esp? How do you even come to a joint decision about how much house you can afford? And one person with no retirement fund vs someone well funded? Does the saver have to double save to care for both? Does the poor one get to go on medicaid or declare bankruptcy? Are you going to let the poor one fend tuition bills for the child?
At some point, finances become entangled simply by living together and co-existing. We don't have a problem with current issues (I bought the house and he became my roommate, which is how we met. So he's been paying rent all along and I don't see that changing, except that now he'll officially be paying part of the mortgage and will be entitled to a share of the appreciation of the house.). But we do need to talk about how to handle future issues. Both sets of our parents are financially stable. But what happens when his son asks for help on a down payment on a house, or gets into financial trouble, or what have you?
And I'd like for him to retire (hopefully young-ish!) someday, too. How is he going to do that with no savings? He has no debt and no expensive hobbies, and he's interested in saving and investing, but I struggle to discuss money issues without sounding preachy or bragging.
Just tossing thoughts around... I very much want us to have a happy marriage, and I know that money issues top the list of marital problems.
So you two haven't discussed your future plans in the entire 7 years you've been together??
It's not preachy or bragging to ask your partner what their plans are and how they intend to accomplish them. Ostensibly, you've at least somewhat discussed retiring at some point, you just haven't gone over the details because you find it uncomfortable???
This to me is like getting engaged to someone who decides in their 40s that they want to be a doctor, but they've never even attended undergrad. Sure, it's possible, but if I was engaged to them, I would sure as hell need to be heavily involved in the planning of how on earth we're going to pull this off as a couple.
It shouldn't be an awkward conversation, this is basic, basic life planning. If it's awkward it's because one or both of you choose to make it awkward, and that means there's something underneath that that needs to be addressed BEFORE you get married. Talking about money in and of itself is not in any way and awkward subject, it just isn't, because everything you talk about involves indirectly talking about money:
"Hey, should we order a pizza?"
Translation: "I consider ordering pizza a reasonable expense, do you agree?"
"I've always dreamed of slow travel in an RV"
Translation: "My travel goals don't involve a lot of costly air travel or hotels"
"What do you think of this top?" [trying on clothes in a shop]
Translation: "Is this top nice enough to justify the cost of buying it?"
"Our bed is getting lumpy"
Translation: "I'm starting to think it's time to invest in a better quality of sleep, do you agree?"
You talk about personal finance all the time indirectly, and it actually takes effort to avoid the elephant in the room of how money plays into all of these conversations. If you're not talking about money directly, then you're both subconsciously engaging in a weird dance where you constantly pivot to avoid it. It may not seem that way, but I personally marvel at the psychological gymnastics people have to do to avoid talking about money in their day to day lives.
Also, if you think that talking about retirement finances will fundamentally make you braggy or preachy, you do realize that that means that you feel superior to your partner? Right? That's an issue. This is supposed to be your equal partner and you don't seem to have much respect for his ability make basic responsible decisions about his future, his child's future, your collective future, etc.
I'm not saying this to criticize you, I'm saying this to draw your attention to the issue that underpins why you aren't comfortable having basic, basic conversations about planning your future with your soon to be husband.
None of these issues are solved by a prenup. A prenup is not a solution for communication problems, particularly because drafting a prenup requires and ENORMOUS amount of communication. If you get into drafting a prenup before you've actually aligned on your financial futures, then you're going to end up paying a fortune for lawyers to act as shitty marriage counsellors.
DH and I knew *exactly* what our goals were, what our philosophies were, and what we collectively felt was equitable before we even sat down with a lawyer. My main concern was that DH never be liable for my student debt that I accrued before our marriage. I was planning on refinancing it as a business loan, so he would have been responsible for half of hundreds of thousands just because I wanted a better rate. The law as it stood in that case wasn't fair due to a technicality, it protected him from previous debt, but if I changed the nature of the debt, it was considered new debt accrued within the marriage.
Had we gone in blind, we would have had to pay the lawyer to explain all of these possible scenarios to us as we figured out how we felt about each of them. Our first discussion about what each of us thinks about the fairness of my debt would have been done in a lawyer's office while they're billing by the minute. It would have been stressful and awkward. Instead, I just said "I don't ever want him liable for my debt" and the lawyer was like "okee dokee, here's how we do that".
We, in fact, make financial conversations a romantic thing. We always go for long walks and frame it in terms of dreaming about our future and how best to strategically make that happen. Since all dreams have a huge financial component, we just don't neglect that part, we incorporate it as a natural part of the bigger picture.
If I were you, I wouldn't possibly marry someone until we were able to have honest, vulnerable, and mature conversations about our collective future. It's kind of the cornerstone of marriage.