Yes, exactly. I'd feel a lot more comfortable with an emergency fund and more retirement savings. And that part about him earning most of the income does indeed feel a bit tricky to me, because I've been reluctant to say, Smarten the hell up, bub, and spend right.
I've encouraged him to read books, watch shows, learn... had soft conversations, intense conversations, but he finds the subject of money boring. We've talked long-term goals, but he just can't seem to stop himself from spending. But it looks like now is the time that I need to get tougher. We had talked of getting married in the spring/summer.
I think you have an opportunity to set yourself up in the role of the financial planner of the couple.
Scare him a bit with your coming cash-flow problems. (Sounds like you're doing this already.) Show him how a $2k car repair bill will break your finances.
Flatter him a bit. Tell him he makes most of the money, and he shouldn't have to be (too) burdened with planning all the finances, and that since you earn less you'll do all the work/planning as part of your contribution to the couple/marriage.
Reassure him a bit. Tell him you can make it all work out, the cash-flow will work, you'll develop an emergency-fund first and then some retirement savings, and that he'll still have (some) spending money.
Then take control, and use your power with benevolence. ;^)
Open a separate account for him, and deposit a regular amount into it that is for him to do with as he pleases. Do this automatically from the paycheck so that it'll be the same cadence he's used to. From this account, he should cover his costs for "personal care", clothes, hobbies, cigars, pocket-money, shows, movies, dvds, etc. That's $800/mo from your current budget, so give him $300/mo at most to start, with the aim of lowering it more in the future. (Ideally he'd also fund his $200/mo trip out of this money.)
Do the same for yourself @ $100/mo. He should feel shamed that he's spending 3x your amount. From your account, cover your clothing @ $20 and the $restaurants @ $40 per month. He should feel humbled that out of your share you are covering your needs and still taking him out to dinner.
This should reduce $800 of expenses down to $400, and still leave you personally $40/mo of your own personal money.
Yes, this is treating him like a child. But in my opinion, that is how he is behaving, so it's appropriate. He needs the training wheels for now, and he needs to see you leading by example.
Additionally:
It seems like you need an emergency-fund right now more than you need retirement savings.
Cut the ipad data.
Your utilities increased 5x at the new house. What's up with that?
Weddings are expensive. Do it meaningfully, but simply and cheaply. And put your foot down to pay for it in cash rather than credit. You can't afford any more credit.