FREE NEWSLETTER

Questions Matter

Go to main Forum page »

AUTHOR: Dan Smith on 3/13/2026

My hat’s off to the couples that got hitched right out of school and stayed that way, happily. That was not my reality. Young love, often ignited by intense physical attraction, often doesn’t ask the hard questions, or require clear answers even if the right questions are asked. And while achieving the age of 73 doesn’t make me an expert, I think everyone is entitled to my opinion, so here goes😉.

That intense physical energy is going to change over time, there had better be a lot more depth to a relationship. Two people with exactly the same interests and personalities could lead to a boring life. Separate interests may add some spice to your life, but you may be in trouble if your mind is closed to new things. He’s not into your seats at the opera, and she’s not into your season tickets to the hockey games, or vice versa. 

My high school sweetheart wanted to get out of town after high school, I had no interest in leaving my home town and family. We broke up, now she has a great life 2000 miles away from Toledo, and I have a great life here. Lucky us.

How about kids? Do you both want ‘em? If yes, is this person going to be a good parent? These may be hard things to know at a young age, but there will be signs. For a budding middle age romance, the questions may relate to grand-kids. Chris never tried to muscle in on my ex-wife’s domain; neither I or my daughters would have wanted that. However, she loves the kids and has made me a better grandpa in many ways, which is something appreciated by everyone. 

How about money? Is money the number one cause of marital train wrecks? I don’t know about that, but it sure can cause lots of stress. Should we save for retirement, or live for today? I’m a split-the-baby kind of guy. As I’ve written before, we should save for retirement, but we better have some fun along the way, in case we don’t make it that far. Balance is key.

When one talks, does the other listen? The listeners out there know exactly what I’m asking, the talkers, not so much. This applies to both friends and lovers. There are a couple friends who I love dearly, but more and more, I barely get a word in, because they do all the talking, always about themselves. I don’t spend too much time with them these days. 

Finally, don’t ignore your new flame’s family. Are they the ‘tail wagging the dog’ kind of in-laws? If yes,  your relationship might be doomed. 

When I became single at 47, I crafted a vision of a future relationship. I did the same regarding my occupation and goals when it became clear that I was leaving the beer business. Those visualizations allowed me to ask the questions that helped lead me to where I am today; happy and secure. 

Major purchases, choosing an advisor, deciding on investments. Questions matter.

How about you? Did you, and do you ask the right questions?

Subscribe
Notify of
16 Comments
Newest
Oldest Most Voted
Inline Feedbacks
View all comments
Edmund Marsh
17 days ago

Dan, I tried to post this morning, but I think the links slowed it down. I’ll try again without the links.

My wife and I didn’t marry until our 30s, the first for both of us, and hopefully the last. From my perspective, I didn’t consider marriage until I had settled into a career. I didn’t have a perfect woman in mind, except I wanted her to be smart. Sharon is my perfect woman–very smart and very tolerant of my quirks.

In his Guide–button at the top of this page–Jonathan has some comments on marriage in the “Life Events” section in the chapter Getting Married. And at the bottom of that page, there’s a link to Check Him Out by Julian Block. As a tax man, I know you’ll like that article.

Thanks for an interesting story.

Edmund Marsh
18 days ago

You offer some great questions, Dan. I married for the first–and hopefully last–time at age 37, I just didn’t feel ready until I’d settled on a career that gave me financial confidence. Even then, I wasn’t looking for a wife, but was open to the possibility. I didn’t know exactly the kind of woman I wanted, except that she needed to be smart.

I found the perfect one for me. Very smart, and very patient with my quirks. We were “family” from the start. And we still prefer one another’s company to any other.

For some other thoughts on marriage, Jonathan offers this from his Guide, and as a tax man, I think you’ll like this one.

Howard Schwartz
18 days ago

A very thoughtful post. Predicting the future is pretty tricky. You do the best you can and hope for the best. Even though half of marriages end in divorce, many people still take the plunge and roll the dice anyway. There are a few bend points in life that determine everything else; whether to attend college, who to marry, what to do to earn a living, where to live. At the end, good luck or bad luck can overwhelm all of your well thought out decisions. My brother always says it is good to be lucky.

greg_j_tomamichel
17 days ago

I agree with the importance of luck. All the hard work and wisdom in the world can be undone by an accident or severe illness.

David Lancaster
18 days ago

As the late great American philosopher Yogi Berra once said, “It’s tough to make predictions, especially about the future.”

Jeff Bond
18 days ago

This is so interesting. Some of my closest friends are my former sister-in-law and her husband. Their kids still call me Uncle Jeff. My former mother-in-law, shortly before she died, told me I would always be her son-in-law.

But the only time I communicate with my ex is about the kids, and those communications are fewer and fewer. We now have very little common ground.

Hard questions, indeed. There are many I wished I’d thought to ask to prevent the heartache I experienced, financial reversals, and therapy I paid for. Luckily, I came out better (much better!) the second time around.

greg_j_tomamichel
19 days ago

Great article, thanks Dan.

I would love to say that I asked careful, rational questions at key points in my life. I would be however be stretching the truth – considerably!

I think we have trusted our gut feel quite often, or the path we took just seemed so obvious to us that we didn’t even think to question which path to take.

Not necessarily what I would advise others to do, but it worked out OK for us.

greg_j_tomamichel
18 days ago
Reply to  Dan Smith

Oh, to be young(ish) again!

David Lancaster
21 days ago

Finally, don’t ignore your new flame’s family. Are they the ‘tail wagging the dog’ kind of in-laws? If yes, your relationship might be doomed.”

We were very lucky that both sets of parents were loved dearly by the other half of the marriage and didn’t interfere, but were adjuncts to our core family.

I think this is obvious by the example that we had my mother in law move from independent senior living to our house at 102 years old and stayed until she passed away approximately one year later.

Mark Crothers
21 days ago

Dan, I get what you’re saying. I think. Maybe.
Full disclosure: I’m probably the worst person to offer advice here. I married my high school sweetheart, and between dating and marriage we’ve somehow accumulated 43 years together, which, depending on your perspective, is either a love story or a life sentence served with great companionship.
Did we have a grand plan? Absolutely not. Did we map out our future? Please! Kids? They just happened,after considerable and enthusiastic practice, I should add.
Money was simply something we earned and occasionally didn’t lose. I stumbled into financial wisdom purely by accident — a chance encounter with a persuasive fellow who talked me into opening a retirement account, which turns out to have been the single most profitable conversation of my life. My wife Suzie landed a job with a large banking group that quietly skimmed pension contributions from her paycheck before we could spend them, and later a government medical department that provided a traditional pension with full inflation protection. The system, it seems, saved us from ourselves.
As for my career? my temperament was constitutionally incompatible with corporate life, which is a polite way of saying I’d have been fired eventually anyway. So I stumbled sideways into a business venture. Nothing planned, just a man following the path of least psychological resistance.
We didn’t navigate life so much as we fell through it and somehow landed somewhere decent.
Which is why I’m genuinely in awe of the younger people in my family who actually have direction, goals, five-year plans. I look at them the way ancient man must have looked at fire — with wonder, admiration, and mild suspicion.
I apparently failed at both direction and planning. And yet here I am.
Maybe that’s the lesson, if there is one: success, personal and professional, sometimes arrives in forms nobody puts on a PowerPoint presentation. Sometimes the unlived plan is the one that actually works, who knows? I certainly don’t.

Free Newsletter

SHARE