Are you compatible sleepers?
Before you can decide if you want to spend the rest of your life with someone, you need to figure out if you can sleep with this person for the rest of your life. I know it doesn't sound like that big of a deal, but it IS. Sleep is EVERYTHING.
Do you want to spend the rest of your life forced to cuddle someone into the dead of night, forgoing feeling in your arm because you didn't know they were a dependent sleeper? No. You don't. Different sleep styles can be awkward in the beginning of a relationship.
One person is a snuggler, a blanket hog, or a ferocious snoring lunatic. If you can't fix the issue with sleep, you'll be deprived of it for the rest of your life. You need to have the "cuddle conversation" long before you pledge your undying devotion to someone. A life without sleep is no life at all.
How messy is each of you?
If you're a neat freak and your partner is a disaster, how will you cope? Can you cope? You'll have to make that call before you get married. Living in filth when you're not down has the potential to make you miserable.
The important thing in this case is whether you're both able to compromise. Maybe he doesn't throw his dirty dishes directly on the floor, but you agree to clean the kitchen after dinner. Perhaps you agree to clean the shower if your husband unclogs the drain. You've got to figure out a way for you both to be comfortable in your home.
Do you want kids?
When you're dating in your 20s, this question hardly seems critical because having kids feels so far off. It's so hypothetical, you can't even touch it. But it's important to find out if the person you're dating wants kids. If you fall in love with someone who feels differently than you on this topic, what are you going to do?
If you don't want children, would you have them to please your partner? Could you handle never being a dad if you wanted to be? It may feel strange to talk about right now, but this information could impact your entire future.
How much debt are you in?
You have to come clean about your financial situation before you get married. You need to reveal your debt, how much you're really making; everything. It will affect your entire life, the least of which is your wedding plans.
It's not romantic to talk money, but going into planning only to find out you can't even afford the flowers is even less so.
A debt of $10,000 is very different from $100,000 -- and the kind of debt also matters. A student loan payment is not at all like paying off a credit card. Having this conversation is essential; and will open you up to figuring out who is going to be financially responsible for what (including past debts).
Who is financially responsible for what?
When you're married, you have to decide who is going to pay for what. You need to figure out if you're getting a joint bank account or keeping your own (or both), if you'll make your partner an authorized user on your credit card, and whether you're going to rent or buy a place.
You also need to know the other person's spending habits. Is someone the saver and the other the spender? Both savers? Both spenders?
This is stuff you need to know NOW, not later.
Is your mother-in-law a crazy person?
Probably, but can you handle it? Assume she's going to be around forever. She's going to drop in announced, invite herself to stay with you multiple times a month, and passive-aggressively insult your outfits.
You may really love your fiancé. But do you love him or her enough to deal with this woman for the rest of your life?
Is one of you going to change your last name?
If there is one thing I hear most often from my married girlfriends, it's that changing your last name is hell on Earth. Everyone gets confused: your employer, the IRS, the post office, and so on. People do NOT love when you change your legal name to something else.
It's annoying and outdated, but a lot of women still want to do it because it's traditional and it makes many of us feel special. You could also ask your new husband to take YOUR last name. What a notion!
Will there be a prenup?
So you're not so rich right now, and might think you don't need a prenup with your future spouse. But what happens if your startup takes off or your book sells? Suddenly, you're worth millions. Without a prenup, you owe your partner at least half.
There are those who think getting a prenuptial agreement is essentially saying you expect to get a divorce. This is just not true. It's protecting yourself financially; it's taking precautions. You don't buy hurricane insurance because you expect your house to blow away, you buy it just in case. The same is true for a prenup.
It's not just about YOU, it's about both of you. Marriage is a wonderful thing, but when you lay it out, bare bones, it's really a business deal. Don't get screwed just because you're in love.