@ebella, here's a for instance. I'm not guessing at your situation; this is a post about communicating.
Do you have a fear of working indefinitely in a job you hate? I get a little of that from your last couple posts, but mostly you say the reverse - that you want financial freedom, you want to pay off debt, etc. However, in your mind, you may draw a straight line through these things
while he does not.This is step 1 of talking past each other.
So say HE has a fear, that you don't know about exactly, that he's not quite telling you (so you get avoidance when you bring up the topic). Say he thinks you'll resent him for not handling his bills and retiring early or something, but instead of talking about that, he's talking about the reverse - doing well enough by you financially that you're satisfied.
Here's what happens: you talk about fixing your fear instead of the fear itself.
Now he reads your signal as the beginning of the resentment he's afraid of.
He addresses fixing HIS fear instead of the fear itself.
He loves you, so he just asks you to give him a number to fix it.
"It doesn't work that way" you reply, perhaps reasonably...
"I can't even fix it??" he hears, confirming finances are just another one of life's unsolvable problems...
I am sure if that sounds plausible to you, it's totally not intentional, and that's all normal (and fixable). It's hard to go from a rut to smooth communication sometimes, but the "opener" skillset is talking about how you feel instead of what has to get done. If you try to quit smoking, for example, the goal and the steps to get there are awfully simple, but that doesn't make DOING it any easier.
You have explained in your last couple posts more about how his avoidance makes you feel - have you communicated these things with him? If so, did you explain them along the lines of (for instance) "Can we talk please? Something is bothering me and I hope we can figure it out as a team - it's causing me a lot of stress. I am afraid of working through my life at a job I don't like, and looking at a future, I want us to on the same page about managing money so I don't have to be afraid of that happening. I feel hurt when you avoid me when I bring up finances, because that fear is what I'm trying to address when I do it. I would love you if you repaired bikes or fixed toilets, and that's not the problem - it's not about the number we each pay for things every month, but about how we look at planning a financial future. Is that ok? If not, can we pick a time to talk about it later?"
This does a few things. It gives the option for him to talk about it later, which reduces the stress of the conversation. It confirms your love for him and that this is not a signal towards any fear he may have - basically, it orients the discussion around YOUR feelings, instead of what he may or may not be doing. This is extremely valuable. The response to "help me I'm afraid" is usually very direct and easy to read! It also sets up the conversation for him to talk about how he feels instead of focusing on totally grasping, right now, "the finances." Listen to what he says and reflect it. Don't defend yourself if he says something and you feel hurt - rephrase to be sure you have it correctly first and check with him if you do. He will feel like you care about where he's coming from, and you may be able to both unwind your anxieties about this.
I like to tell the story of driving around happily in a hilly area with lots of curvy roads. My girlfriend at the time was not having a swell ride because she was getting nervous, but she didn't talk about that, she remarked sarcastically about the speed limit and my ability to read. I was angry, because I am like, SO GOOD at reading street signs! Actually, I was angry because I felt I was being blamed for her anxiety about "perfectly reasonable" speeds, and that hardly seemed fair to me. So I said how I felt about her comment, and got her to say she felt unsafe, which I totally didn't want, so I said if she ever felt afraid or unsafe, and she told me that instead of impugning my ability to read, I would always slow down for her. She tried it once, couldn't believe it worked, I wasn't annoyed about the sarcasm anymore... everybody won. But it can be hard to talk about the issue directly, sometimes. We feel more vulnerable doing it, and we can get carried away in completely irrelevant conversations very easily.
Though these "for instances" of talking past each other may not hold bearing on your situation, they're the sort of thing a therapist is supposed to help you do in counseling, and you may find a pre-marriage or couples therapy session extremely helpful. We often think of therapists more like mechanics you go to when something is broken, rather than facilitators for communication and health, but they're way more valuable as the latter.