Wealthsimple is a whole new kind of investing service. This is the latest installment of our "Dear Ms. Etiquette" series, where our columnist untangles the issues that happen when people and money get together.

Gosh. I have so many questions for you, Ms. Love Contract. So many! Like: Why do you think you need a prenup? That’s a question I’m going to ask. But we should cover some stuff before we get there.

Let’s start with the basics: A prenuptial agreement is a written contract created by two people who are planning to be married. It typically lists all of the property you both own, your assets, and your debts — and it specifies what will happen to those assets and debts (as well as those that accrue in the future). It’s also common for prenups to include a kind of timeline. As in: If we divorce after two years, I’ll give you X amount of money, each month, for two years; if, on the other hand, we last five years, the number jumps to Y figure per month. And so on. (Prenups often seem to be saying, “The longer you can tolerate me, the more money I’ll give you when you realize you can’t take it anymore.”) Sometimes prenups come with expiration dates (more on that later), but most are until divorce or death do us part.

Before we get to the fun part — about whether prenups make you a bad person — let’s go over a few really simple guidelines so that if anyone ever asks you (or if you, Ms. Love Contract, ask someone else) for a prenup, you don’t end up getting taken for a financial ride. We’re all about protecting you from the fine print at Wealthsimple.

Don’t hide any assets. If additional assets are discovered after you’re married, the prenup could be tossed out.

Don’t spring it on anyone. You’ll want to avoid what lawyers call a claim of coercion. Specific deadlines — how close to the wedding day you’re allowed to ask — vary according to local laws.

No one can talk about child custody or child support in a prenup. It’s about marriage, not procreation.

If you want an expiration date on the agreement, you’ll have to ask for it. It’s called a sunset clause.

No one’s allowed to throw in any language that promotes divorce. For instance: “If you cheat on me, I can get a divorce.” Although, if one wants to take a lesson from Jessica Biel, I read a juicy account of her prenup with Justin Timberlake, which reportedly included a cheating clause that stipulated she would get more money if he strayed. It didn’t say anything about divorce, though.

Smile for the camera. This came as a surprise to me, but it’s common for the signing to be filmed in an attorney’s office. “You need to prove that you are of sound mind and body when you sign,” explains my friend Louis, who's been through the process. Huh. Makes sense, when you think about it.

I will allow that rational, normal people can, and do, disagree about whether a prenup is a practical, and even positive, marital instrument or whether asking for one makes you the worst. On the pro side: A prenup gets everything out in the open, about your finances especially. The well-known New York divorce attorney Raoul Felder says, “Anybody who’s getting married and doesn’t have a prenup ought to see a psychiatrist. The point is to protect yourselves in the future.” He adds that a prenup can actually prevent divorce. “I always say the goal is to keep you married, not get you divorced,” says Felder. It can also save you from insane legal bills and prolonged court battles in the event that your marriage blows up.

The other side, of course, is that a prenup is coercive, cold, and calculating, and it puts a bad taste in mouth of the less-moneyed spouse-to-be. There’s a risk in marriage. It’s a leap of faith. There are stakes. If you can't handle that, don’t get married.

In fact, I’ve devised a handy-dandy guide to help you figure out when it’s a good idea, or at least permissible, to ask for a preunp.

But first an important message from a rabbi.

Even if you don’t get a prenup, have that brutally honest financial conversation before you are married.

When I asked Jonathan Blake, the rabbi at the Westchester Reform Temple in Scarsdale, New York, about prenups, he told me something important. Like, really, financially important. Rabbi Blake performs a lot of marriages. And he couldn’t believe how many of the couples he marries enter into their eternal union without knowing the answers to certain significant questions: How much debt do you have? Are you in possession of a trust fund and, if so, of precisely what size? Is your credit so bad that you can’t take out library books? And what about the future? Is someone going to want to be a stay-at-home parent? Are we talking public or private school?

Money is taboo, but you avoid the topic at your own financial and marital peril.

“It kind of surprises me how much I talk about financial stuff as a rabbi,” Blake says. “But it’s the number-one topic of conversation in my work with young couples.” The good rabbi wants you to have the talk. He also recommends sitting down with a financial planner. “There’s often work to be done in terms of outlining financial goals, priorities, income projections, and especially debt,” he says. “I think one thing young couples haven’t wrapped their heads around in many cases is that they each assume the others’ benefits and burdens.” I’d argue that’s what marriage is about: to have and to hold each others’ burdens, in sickness and in wealth. And prenup or not, you still need to share that information with the burden-sharer.

OK. Now let’s get into who should, and should not, consider a prenup.

Here are some reasons a prenup can be seen as practical:

  1. You entered into this relationship with a ridiculous amount of money. My friend Louis, who has a prenup and is happy he does, explains it like this: “I had worked very hard at making this money over many years. If we divorced, I would, of course, provide for her,” he says. “But it seemed unfair that she’d be entitled to half of all that I’d made.” I understand where Louis is coming from. If I were him, I’d also be paranoid that anyone I met wanted to be with me for my money.

  2. You spent the last five years building your start-up, and it’s about to go off. Warning: You risk sounding like (and possibly being) a jerk if you say the previous phrase.

  3. It’s your second (or seventh) marriage. I get it. Once bitten, twice shy. But don’t be transactional about it, OK ?

  4. You met your significant other 10 days before the wedding. Or are a contestant on The Bachelor/ette.

  5. You are deeply in touch with, and yet petrified by, the fact that the future, and human beings, are unknowable. Prenups can seem brutal. But so are divorce statistics. And you’re not so hubristic to believe all those divorced people are dumber than you.

  6. You’re Brad Pitt. Have you ever been happier that you’re neither a billionaire nor Brad Pitt?

OK, back to you, Ms. Love Contract. If you’ve read all of that and still think you should ask for a prenup, here are Ms. Etiquette’s guidelines to asking without being a terrible person.

  1. Have good timing. My first question for you: When did you tell your boyfriend that a prenup was going to be required? Because if you say, “Oh, I haven’t mentioned it yet,” I’m going to say, “You deserve a glass of champagne, or at least soy milk, thrown in your face.” Do it early, but gently. At the first inkling that things are getting serious, mention to him that it’s something you’ve always thought would be a good idea.

  2. Probably don’t announce it via fax machine. A friend tells me this story: “Weeks after Will, my fiancé, first came home and told me his father wanted us to do a prenup, 35 pages spat out of my fax machine at work. It was done completely without our input. It was egregious and punitive. It certainly didn’t come from a place of ‘Welcome to the family.’”

  3. Be superhonest about why you’re asking. This is a chance to start out your life together with honesty. Tell your fiancé what you’re scared of. Was the idea really yours or did your dad, or your business partner, plant the seed? If you’re embarrassed about that, face up to it. It’s a good opportunity to either stop being controlled by those outside forces or admit that you like their influence (and possibly the inheritance that goes with it). If he finds out later that your rich grandmother made you do and you never fessed up, “What a wonderful surprise!” will probably not be the response.

  4. But don’t think you get a free pass just for being honest. Listen, you unburdened yourself. Mazel tov. But you may be laying some heavy stuff on your affianced. And this person shouldn’t be expected to automatically accept it all. He might be hurt, and that’s a fine place to start.

  5. Consider a mediator. Lawyers can be adversarial. Mediators don’t take sides. “A mediator should bring up the thoughts and concerns of both parties in a nonconfrontational way,” says Laurie Israel, a lawyer who is working on a book called The Generous Prenup. “Going to a mediator can encourage truthfulness and clear communication, and it also helps train the couple to discuss and resolve difficult issues.” Even if your mediator also happens to be an attorney (which Israel highly recommends), the mediating attorney can’t be the attorney who drafts the prenup.

  6. Tell him you’ll pay for it. This was your idea. He can choose the attorney; you can foot the bill.

The point of a prenup is an important one. All marriages are breakable. And that’s actually a helpful, and beautiful thing.

Let’s end with some more rabbinical wisdom. “The bummer of the prenup is that it begins from the premise of divorce,” says Rabbi Blake. “I reframe it by asking, ‘If you’re aware that marriage is a fragile thing that could end in divorce, won’t this make you more zealously protective of your relationship and your marriage?’ Knowing that marriage isn’t something on autopilot and isn’t going to protect itself is a motivation for the couple to protect it and nurture it.” Only your investments, after all, should be on autopilot. (That’s a Wealthsimple-ism. Didn’t you know?)

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