Is Asking for a Pre-Nup Asking for Trouble?

How I asked for a prenuptial agreement and lived to tell about it

You’ve practiced the wording. Maybe even rehearsed in the mirror. You hope she’ll say yes—your heart tells you she will—but still there’s that nagging uncertainty that her feelings may not be the same as yours. As the big day approaches, you plan every detail: the restaurant, the menu, the precise moment to pop the question.

Finally, it’s time to take what feels like the biggest plunge of your life: “Honey, you know I love you and always will. You are the person I want to spend the rest of my life with, for better or for worse. So darling, will you…sign a pre-nup?”

For most men, asking for a prenuptial agreement elicits more anxiety than proposing. If she’s already said yes to marriage, will she back out now? Or, if you haven’t popped the question yet, should you ask for a pre-nup first? Will it ruin the romance? Will she curse you out and dump you faster than rats leave a sinking ship?

When to start talking about it
Regardless of your anxiety or fear of flying objects, it is always best to raise the issue of pre-nups as soon as is reasonable in a serious relationship, so your partner doesn't feel blindsided. Obviously the second date is too early. But the second month is not, and the second year is too late. Waiting for the last minute is asking for problems. Just as the topics of religion, children, finances, and living arrangements should always be discussed long before you become engaged, the issue of pre-nups should come up early—and often—in your courtship.

But how should it be done to ensure the best outcome (i.e., no tears, no weapons)?

First, it should be brought up in the context of an overall discussion about the finances of your relationship. Set aside a time (agreed to by both people in advance) to go over your current finances, what each of you earns and owes, what assets you are bringing into the relationship, and how you see your finances working once you are legally a team. (Make no mistake, marriage is first and foremost a legal contract, just like a mortgage. All the love and optimistic hopes in the world does not negate that reality.)

Why ask for a pre-nup in the first place?
If you are bringing significant assets into your marriage, make sure your partner knows exactly what those are and how you acquired them. Did you inherit assets or a business? Did you build up wealth through your career? Is your future earning power a direct result of investments you made in your past, be those financial investments (a business you started) or investments of time and effort (going to medical school and taking out loans to pay for it)? These may be assets you want handled differently than normal income earned during the marriage.

If you inherited some of your wealth, from whom? And what were that person’s wishes for how you would distribute those assets in the future? For instance, if you inherited your father’s business that bears the family name, was it his wish that it stay a family business throughout the generations? How would you (or he) feel if that business became you ex-spouse's as a result of your divorce or death?

Divorce and community property laws vary from state to state, and it’s beyond the scope of this article to give legal advice. But just know that even in marriage, there can be separate assets owned by each party, and you need to at least consider how you want to control those assets in your future marriage and beyond.

One man's story (mine)
But back to the question at hand, how do you ask for a pre-nup? I suspect there are as many ways to approach this thorny issue as there are unique snowflakes.

So I'll just tell you how I went about it and the obstacles I met.

When I met my future wife (who I'll call "S"), I was already in my mid-thirties and a very successful TV writer. Because I had worked my way up the showbiz ladder and invested my earnings wisely, I came into the relationship with significant assets, including a big house and a well-funded pension plan, whereas S came in with an old VW Rabbit, a clock radio and a mattress.

I let S know early in our dating life that I had worked hard to build up my net worth and intended to keep those assets in my name should I ever get engaged. I also told her that I would never get married without a pre-nuptial agreement and asked how she felt about that. Because it was early in the relationship, S probably saw the question as an abstraction and seemed fine with the idea.

In time as I began to think that this was the person I wanted to someday marry, I made sure to casually bring up pre-nups now and then just to make sure we were still on the same page. So by the time I proposed, the issue—at least hypothetically—had been resolved.

First, let's kill all the lawyers
Soon after I popped the question and S said yes, I found an attorney to draft the pre-nup and he explained the basics. He also told me that S had to have her own independent legal counsel review the agreement, and he gave me three names to suggest to her. (Of course, she was more than welcome to find someone not on our list, which she did.) My attorney drafted an agreement, we reviewed it and made changes, then sent it to S and her attorney to consider.

Then time went by. Weeks. Months. The wedding arrangements were going forward, invitations were sent out, locations were rented, bridal gowns and tuxedos were purchased and fitted. But no reply to the pre-nup. After quite a bit of coaxing by my lawyer and me, her attorney finally replied: our draft was totally unsuitable and had to be scrapped. This led to some very testy letters from her counsel, and I began to dislike her lawyer even more than the kid who beat my up every week from third to sixth grade. (Whom, by the way, I found infinitely more reasonable than this guy.)

After some unproductive back and forth between the lawyers followed by weeks of radio silence from her counsel, S decided that her attorney was not working in her best interest and changed lawyers. I was relieved and hopeful that our pre-nuptial impasse would soon be bridged. Ha!

What followed, while I was working on a TV series in Toronto and living 2000 miles away from my blushing bride-to-be, was three months of the most tense, invective-filled negotiations I've ever been a party too. Her attorney simply didn't want S to sign a pre-nup—of any kind!—and would redline out clause after clause until virtually all that was left was the opening "Whereas" and the final "Executed on this date."

Second thoughts and weak knees
For her part, S was becoming a bit reluctant on the subject. Why, she kept asking, did we need a pre-nup if we were going to be married for the rest of our lives? I patiently explained again that while marriage was a demonstration of our love for and commitment to each other, it was also a legally binding contract that had practical, very unromantic financial implications if the marriage did not last forever (and many do not). If S were to marry me, she'd be stepping up to a lifestyle well beyond what her career and income at that time would have afforded her on her own. And that was fair as long as we were together. But if we were to separate, why should I be obligated to keep her living in that same lifestyle when it was based on my work and savings all accumulated before I ever met her?

That said, I felt S did deserve a secure future built on the financial foundation of our years together, and I assured her that the agreement we ultimately sign will create adequately sizeable community property to ensure that if we ever should part ways, she will not come out empty handed. As a show of good faith, I even put the house we were living in—purchased solely with my own money—into both our names, and made it clear in the pre-nup that any equity we built up in the house would be community property shared equally by both of us. (It did build up substantial equity, and when we sold it the profit became community property as promised.)

Even though S was back on board, her attorney was still holding out for a better deal. With the wedding now two months away, I implored S to talk to him and help us bridge the impasse. She said she did, but the negotiations still didn't seem to be making progress.

Finally, with a week to go before the wedding, a four person meeting was held—S, me, and our respective lawyers. Was it romantic? No. Was it unpleasant? You bet. Were tears shed and insults hurled? Uh, yah! (The insults were from her lawyer, toward me.) Did we come to an agreement that all the parties thought was equitable? Well, I don't think her attorney ever liked the final draft, but everyone signed it and the wedding went forward.

The upshot of the story
I'm guessing you know how this romantic comedy ended. S and I married, have two great kids, and are now, alas, divorced. I won't lie to you—she was not very happy about the existence of the pre-nup when we were working out our divorce settlement, and she might have gotten more without it. But we came to a settlement agreement that includes spousal support and child support at the levels normally dictated by California family courts, as well as a fairly sizeable sum of cash to buy her out of our house and other comingled assets. I also created a trust fund for the kids and agreed to contribute a specified amount every year to their college accounts. None of that was in the pre-nup, but it's in the post-nup.

I learned a lot going through that experience. It ultimately saved me and my ex the pain and cost of going to court, and it made a difficult process much quicker and saner to get through (even with a new set of attorneys and a new round of invectives). I won't say coming to an equitable divorce settlement was particularly easy or pleasant, but I feel having a well-crafted pre-nup in place ultimately worked out well for my kids, my ex-wife, and myself.

And when someone very dear to me recently told me she was getting engaged, I said I have two words for you: "Congratulations!" and "Pre-nup!"