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Horizons: Family Office & Investor Magazine

The 12 Questions to Ask Before You Marry Someone

Monday, September 19, 2022

by Whitney Tilson - an excerpt from his latest book, The Art of Playing Defense: How to Get Ahead by Not Falling Behind.

Whitney Tilson is the founder and CEO of Empire Financial Research, which launched in April 2019 and provides advice, commentary and in-depth research and analysis to help people become better investors. The business now has seven newsletters and 100,000 paid subscribers. He has also (co-)authored several books on investing (including Poor Charlie’s Almanack).

In the year prior to launching Empire, he founded and ran Kase Learning, through which he taught a range of investing seminars around the world and hosted two conferences dedicated solely to short selling.

Mr. Tilson founded and, for nearly two decades, ran Kase Capital Management, which managed three value-oriented hedge funds and two mutual funds, with assets that peaked at over $200 million.

Tilson graduated magna cum laude from Harvard College with a bachelor’s degree in government in 1989. After college, he helped Wendy Kopp launch Teach for America and then spent two years as a consultant at the Boston Consulting Group. He earned his MBA from Harvard Business School in 1994, where he graduated in the top 5% of his class and was named a Baker Scholar.

1. Are they a warm, kind, and good-hearted person, both toward you and others? Do they have a mean bone in their body? How do they treat people like employees, waiters, and taxi drivers? Do children and dogs like them?

This is so important—and it’s so easy to be fooled because, of course, the person you’re dating is going to be on their best behavior around you. That’s why it’s critical to watch how they treat others, especially those they don’t perceive to be peers. Children and dogs are often much better judges of character than you are!

2. If you weren’t romantically interested in each other, would you be close friends? Do you make each other better?

Over time, when the passion and romance aren’t so intense, there had better be a solid foundation of friendship, or you’re in trouble. You want to be with someone who gives you frank feedback and smooths your rough edges—as Susan regularly does with me!

3. Do they have high integrity? Are they a stable, solid, predictable person who you can count on 100%? Do you trust them completely? Are there any issues with anger management, violence, narcissism, alcohol, or drugs?

There can be no compromise in this area. If you don’t trust someone with your life—if you’re not 100,000% certain that they would never cheat on you or knowingly hurt you, directly or indirectly, in any way—then RUN! If you find yourself rationalizing, “Well, he’s great most of the time, but sometimes when he’s had too much to drink...” RUN! One of my friends who’s dated a lot of people told me that many of them can’t “relax and be themselves” until they’ve had many drinks. If you observe this, RUN!

4. Do you share core values, e.g., self- improvement, giving back/philanthropy, meritocracy, humility, life balance, spirituality, thinking before acting, looking for win-win solutions?

Every person’s list here will be different. I thought about adding “political views,” but you’ll have to decide that for yourself.

5. Are they intelligent and intellectually curious? Do you find them interesting?

This isn’t code for “did they attend an elite college?” My dad is from a prominent family in Connecticut and went to a private high school before attending Yale, while my mom is the daughter of a Seattle fireman and went to public schools all the way through the University of Washington. So what? They’re both smart, intellectually curious, and interesting—and have been happily married for more than 58 years!

6. Do they like to do fun things and have a zest for life? Are they a happy and optimistic person? Do they have a good sense of humor and make you laugh?

There are so many people who look great on paper— they’re nice, went to a good school, have a solid job, etc.—but are just, well...boring. You don’t want to be married to someone like that unless that’s what you’re looking for, of course!

7. Do they have a strong work ethic and a purpose?

Initially, this question was “Do they have a good job or career,” but I changed it because some people choose to do things like write books, raise kids, or do volunteer work—and they’re very happy and are wonderful spouses. The point of this question is that if you’re a driven person and your spouse is a lump, your marriage isn’t likely to last.

8. Do they come from a stable family? Do you want to spend time with them (because you will!)?

The first part of the question here is tricky because it seems unfair to hold it against someone if they happen to come from a messed up family. But I’ll be honest: I’d rather see my daughters marry guys whose families are similar to ours—filled with deep, long-term, loving relationships.

9. Do your friends and family like them?

Similar to the dogs and children question, someone may be able to fool you...but they’re unlikely to be able to fool all of your friends and family. Ask people close to you what they think—and listen carefully!

10. Do they have similar views on big issues such as where to live, children (how many, what religion, how will child-rearing duties be split), whether one of you will stop or cut back on working to raise the kids, and finances (spending habits, lifestyle, debt, the importance of having a lot of money)? Will they be a good parent?

As your relationship deepens, you’ll want to think about these things—and have some conversations about them, however difficult that might be.

Regarding religion, I remember on my first date with my wife, I told her we could raise our kids Jewish. It was certainly premature—I said it with a smile— but it’s a critical conversation to have if you and your potential spouse are from different religions. (I wasn’t raised religious, so it wasn’t a sacrifice for me—and I’m delighted that my daughters are Jewish, as I fully embrace the values of the religion.)

Another huge issue is balancing both of your careers with the demands of raising a family. A lot of guys have the sexist assumption that their wives will sacrifice their careers once kids come along, which can lead to anger, resentment, and, eventually, divorce.

11. Have they had long-term relationships in the past? How have they ended? What would previous boyfriends or girlfriends say about them?

When deciding whether to raise children and spend the rest of your life with someone, you should be less concerned with how someone is 99% of the time than with how their worst 1% looks like. Observing or talking to ex-partners is a good place to start.

12. Do you think they’re attractive, and do you have a wild, passionate sex life?

A good sex life is an important element of a healthy marriage, but I have deliberately listed this as the last and least important question in part because so many young people seem to put it first. I know a number of guys who are trapped in miserable marriages with women who are mean, shallow, or otherwise unpleasant—but, boy, were they hot and sexy when they were younger! To quote the old adage, these guys let their little heads think for their big ones...and have been paying a big price ever since.

I am not saying that you need a perfect answer to every one of these questions. Every person might have a slightly different set of questions, prioritize them differently, and think differently about what flaws can be overlooked. For example, can you live with someone who occasionally smokes marijuana? Or has very different political beliefs? Or spends money more freely than you? What if you want to raise the kids in your faith, but your potential spouse wants to let them decide for themselves? There are no easy answers to questions like this.

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