Proposals are a thing I’ve watched multiple friends and myself completely and utterly blow, on multiple levels, for multiple reasons. A lot of them come down to basic things like “you don’t know what you’re doing,” or “you didn’t think about it” or “you took someone else’s ideas that sounded great, because they were his or her ideas for his or her relationship.

The best ones I’ve seen have got a great deal of thought put into them. Some are expensive; some are cheap; some cost literally nothing. What’s a commonality in all of the great ones is that the actual proposing is only half the battle. The rest starts way, way before.

Here’s what you should do far before you propose to your soon-to-be fiancée.

She may sing like a dying animal in the shower. You may fart like a wildebeest, and she may find that so gross that sleeping next to you is awful.

Live together for 6-12 months.
You don’t just need to be madly in love; you need to be good housemates. You are going to live with this person forever. Only after mutual close space-sharing can you truly understand if you’re right together. Yes, she’s going to see you do something embarrassing—really embarrassing—and see you at your absolute weakest. You’re going to be blubbering about something that really breaks you, and she has to see that. Conversely, you need to see that in her, too.

Plus, she may like to design in a particular way. She may sing like a dying animal in the shower. You may fart like a wildebeest, and she may find that so gross that sleeping next to you is awful. You may get news that turns you into an emotionally uncontrollable monster, and vice-versa, and both of you need to deal with it and still love each other during and after those experiences.

Also, erm, girls have periods. You will learn way more than you currently know about periods when you live with and love someone that is female. This is not a statement of me speaking to know any of the pain and suffering that a woman goes through monthly. But you’re gonna need to learn to be there for her. If you’re the kind of guy who says “ew, blood” or “just doesn’t wanna hear it,” you’re in trouble.

Basically, you need a significant amount of time in a vulnerable, open state—the good and the bad. This also means supporting each other in bad times, and really, it also means celebrating good times together. It actually hurts a great deal when something great in your life happens and the other person, used to your presence, acts with ambivalence.

No matter how high you’ve been flying, you’ll be brought down to earth when a tow truck shows up for your Audi just after you spooged.

Kids, religion, finances—Analyze your deal-breakers.
Do you want kids? No? Okay, she better not want kids either, because if she does, you’re not gonna work. Or if she can’t have kids, and you can’t deal with adoption for whatever reason, you’re also not gonna work out. Or maybe you can compromise. Does she want to get married in a church and you want to get married in a synagogue? Better find a compromise. Does she want to circumcise your kid, and you don’t? How much do you care? Because if she really cares and you don’t care much, that’s a compromise.

The phrase “happy wife, happy life” can be used to keep you in remarkably abusive relationships in the wrong hands—but it’s predominantly an accurate statement. If you really don’t give that much of a shit about something that she really cares about, but you’re a stubborn dick, I really recommend not being such a stubborn dick. Nevertheless, if you really do care that much, that’s a deal-breaker.

In essence, you have to learn to compromise, and learn what you simply can’t tolerate. There’s nothing wrong with admitting that something is not going to work because something fundamental to who you are in the world is not fitting with your partner. It may be strict political or religious beliefs, or having kids, or even how you split your finances.

Finances are also a huge part of the equation that never, ever goes well if you don’t have a conversation. You should be as upfront as possible with debt you have. You don’t have to be precise to the decimal point, unless not being so exact is a deal-breaker for one of you. But if you are swimming in debt, multiple years behind on your taxes, liens on your car, she needs to know, and if she’s in this situation, so do you. It may actually work out. It’s just a case of being honest so both of you know what you’re getting into. You’re going to live together forever, theoretically.

To quote my girlfriend, “I hate that shit.” That’s how painful that conversation can be. But you need to know the complete truth. So does she. She may turn around and say “I can’t take this.” That sucks a lot of ass, but it’ll suck so many more asses if she finds out when you’re married, and she legally inherits that debt. And if you let her unknowingly inherit your debts through marriage, you’re a subhuman piece of shit.

You will, as a guy, be 100 percent embarrassed to talk to your girlfriend about debt. It’ll hurt. It’s humiliating. Trust me, I’ve had a shit ton of debt in my life. I’ve dealt with it. Then again, that’s nowhere near as bad as the guy I heard about today whose beautiful Audi, that made him look quite the baller, was repossessed post-coitus. No matter how high you’ve been flying, you’ll be brought down to earth when a tow truck shows up just after you spooged.

Come clean with any horrible shit in your life.
If you’ve got something that’s happened, you want it out in the open pretty early on. Been to prison? Tell her. Felon? Tell her. Have sex with a horse? Don’t tell her unless there’s a video. Even then, find the video, kill the guy who has the video, burn every copy, get rid of the horse-sex video. You do not want the horse sex video out there. I’m serious. You need the damn horse video gone. Burn down the building housing it. That horse is going to ruin your life.

But seriously, you need to come clean with any grizzly details in the past that have happened to you. Yeah, if you say, “Hey, uh, so I went to jail” on the first date, I’m guessing you don’t get a second one. But a few months in, it’s time to start talking to her about these things.

Everyone has shit that’s happened to them in their lives or things they’ve done that they’ve regretted (that aren’t necessarily bad but are, well, controversial)—horrifying relationships (by this I mean someone who you truly think will endanger you or both of you), alcoholism (goodness, do not hide alcoholism), you were a male stripper, you’re divorced, you went bankrupt, you had a stalker (or have a stalker!). Shit that if you hide from them, and they find out later, they might feel betrayed.

You want that out there for three reasons:
1)    If it’s going to end your relationship you really want to do that before you have to go before a judge to do so.
2)    It will get potential arguments out of the way.
3)    It will engender trust and closeness in the relationship.

Don’t get creepy, weird close with the parents. I’ve seen friends spend as much time with their wives’ dads as they do with their wives, and it makes things uncomfortable. But, hey, if you get on well, that’s brilliant.

Both of you need to meet the parents and ask permission (maybe).
It’s going to be a problem if you can’t at least get on with each other’s parents. I don’t mean that you’re outside throwing around the ole pigskin, slapping each other on the back like a Wrangler’s commercial, or standing in the kitchen baking pies with her and talking about how many babies you’ll have. I’m saying you can have a conversation, you don’t look like you’re going to stab each other and they’re not actively saying, “Oh great, does he have to come around here all the time?”

This is especially true if said potential wife is super, duper close to said parents. In which case you are not going to win the war if they dislike you. Sorry, man. If you don’t at least find a way to be cordial, and they live near you (under an hour) this will 100 percent of the time fuck up your marriage. They’ll drop in. You will argue. It will be bad. This counts on both sides. You may be more tolerant than her, but even if you get married, it will be so, so bad.

Conversely, if you can get on with the parents, or even be friends with them, this will make your marriage a lot easier. Don’t get creepy, weird close with them though. I’ve seen friends spend as much time with their wives’ dads as they do with their wives, and it makes things uncomfortable. But, hey, if you get on well, that’s brilliant.

When it comes to asking permission, you should ask whoever is considered the person who raised them. It may be their father, their grandfather, their godfather, their godmother, their uncle. Ask. If they say no, well, shit, you may go right ahead and propose anyway, but you will revert to the previous problems.

So now you know you’re ready to propose (or not). Tune in next week for how to shop for the ring and do the damn thing.

Photo Credit: Twenty20/@zacharygilbert

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