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Questions Matter

March 13, 2026 by pfb

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?

The post Questions Matter appeared first on HumbleDollar.

Filed Under: Personal Finance

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