Tell Me About It: Wanting to be married vs. being ready for marriage

Adapted from a recent online discussion.

Question: I have been dating my boyfriend for almost four years. When we met, he told me he was separated, and I later learned they still lived together due to financial reasons. Reportedly, the reason for the separation was that she had a years-long affair. The first couple of years were ridiculous: He wasn't completely honest with me, I accused him of lying to me about being separated, etc.

Since he moved out two years ago, our relationship has been great. We get along, have a lot in common, and always have a great time together. I am at the point of wanting to move forward with our relationship - after all, it has been nearly four years.

When I recently asked him when he intends to get a divorce, he was very defensive (although my timing was terrible - we'd been out drinking). A couple of weeks later, he (unprompted and out of the blue) vowed to "work hard" on getting the divorce done so "we could be together all the time" (we do not live together).

So far, I have seen no evidence of his "working hard" to get divorced. I think he feels bad because he carries the medical for his wife and she has no insurance available through work. But she can get Obamacare now!

What do you make of this? Fear of commitment? Not wanting to deal with young children again? Embarrassment because (he probably knows) I make more than twice what he makes, or maybe he has a lot of debt and he doesn't want to have the "financial discussion"? Is it time for an ultimatum? I hate to pressure him; I want him to want to marry me! Thanks!

Answer: So, he lied - and not a white lie, but a marital-status whopper; he gets defensive about sensitive topics; you need a couple of belts before you can broach a sensitive topic yourself; you know nothing certain of each other's finances; you haven't talked about or don't believe what he's said to you about having children; you haven't received any insight from him about why he's moved so slowly on dissolving this marriage - but you have a lot in common (indeed) and have a "great time."

This is coming out more mean-spirited than I intended, but I'm in full wow. You just sound so achingly unprepared for marriage.

Before going in, you need to trust each other implicitly and feel comfortable saying what you need to say - and that's just one of many ingredients for a healthy marriage. You don't appear to be even close to that point with each other.

What you're doing in your letter is just mentally running through various scenarios to try to figure out what he is thinking and why, and, apparently, you're relying on that as your primary mode of communication. That's how people end up marrying someone who has ideas and goals that are completely different from their own.

Find a way to talk to each other - about everything and anything, no more lies and no more rationalizations. When you actually know how he feels about insurance, income, kids, divorce, and commitment - because he has told you himself - then write to me about wanting to get married.