The Hard Questions: 100 Essential Questions to Ask Before You Say “I Do”
Tarcher/Putnam 2002
$15 hardcover / $10 paperback

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If you’re thinking of getting married or otherwise settling into one relationship, congratulations. You are fortunate, brave, and, if you’re like the rest of us, terrified. Nobody wants to get divorced! The Hard Questions can help.

For our parents and grandparents, these questions were probably not necessary. The conventions of marriage were understood because most often, marriages took place between people of similar backgrounds. But today all bets are off. Extra effort is required to see through your projections of “the perfect partner” and instead see the perfect partner in front of you, exactly as he or she is.

Asking The Hard Questions is a way to create intimacy that can last beyond the first blush of romance. This way, when you finally do say, “I do” you will know what you’re promising and whom you’re promising it to. And what is more loving than this?

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About the Book

When I was thinking of getting married (almost 10 years ago now, I cannot believe it), I got really panicky. I mean I loved my boyfriend and everything, but so what. All my divorced friends loved their boyfriends when they got married too. I thought really, really hard about whether or not to go through with it (obviously; I wrote 100 questions before I said yes) and I also reflected about (all) my past failed relationships. And I had a startling realization. None of my past serious relationships failed because we didn’t love each other anymore. It was not a matter of love at all. These relationships failed because one of us didn’t love our life together. We were unable to create a LIFE that we both loved. I was kind of shocked when I thought of this: you mean just because you love someone doesn’t mean you’re going to love your life together?? No one had ever said this.

So I started to write down questions about our life.

Would we keep our money separate or together?

What holidays would he celebrate?

What would his son call me?

How satisfied were we with each other’s level of ambition? (Could be too much, could be too little.)

Where would we live? (At the time we lived in two different cities.)

How long will we live there?

What if one of us wants to stop working?

Will we have kids and if so, when?

Answering these questions proved to be an amazing experience. And believe me, it’s not like we agreed on everything. If fact, we probably agreed, disagreed, and drew a blank in equal measure. But here’s the thing. We loved, loved, loved each other so much when we were done answering the questions. WHETHER OR NOT WE AGREED WITH EACH OTHER. That was key. There was something so endearing, empowering, and–yes–loving about having this kind of conversation together. We felt so close. And let’s face it, all of these questions are going to come up anyway. So best to have a look at them sooner rather than later. The Hard Questions contains these and other questions designed to help you see exactly how the other views life—not so that you can concoct a matchy-matchy outlook, but to discover the contents of your beloved’s heart.