Questions You’d Really Like To Ask

When people first start dating, they’re young and there’s not that much history for them to stumble over (though I do recommend they take this guide to marital compatibility). It’s pretty much limited to these questions: 1) where you want to go to college, 2) what do you want to do for a living, 3) do you want kids, and 4) are you a registered sex offender?

When people start dating later in life, there’s a little more baggage that needs to be explained, simply because we all have more hours in the air. But the other thing that happens as you get older is that there’s a whole lot more to be suspicious about. It’s no big deal if you’re in your 20s and meet another person in their 20s who isn’t married; that just seems like the order of things.

But if you’re middle aged, and someone’s single, you’re naturally curious about the history of their relationships and their ability to sustain them. Sometimes things happen: you read about it all the time in Dear Abby’s advice column. All of a sudden, what had been a loving spouse suddenly professes a love for another man, another woman, a new career found only in Tasmania, bowling; the list is endless.

The problem is, it’s not polite to ask these questions, as much as they may be bursting out of you. As the Australians say, what happens in Tasmania, stays in Tasmania. It’s even worse when you’re not even the one in the new relationship. It could a new someone in the life of someone you love. As a public service, we present the questions you’d really like to ask:


● Have you ever been married?
● How many times?
● Were they all the same gender?
● Did you leave them? If so, why?
● Did they leave you? If so, why?
● Did they die? If so, was it contagious?
● If it wasn’t contagious, was it an accident?
● If it was an accident, can you prove it?


● Have you ever been arrested? Indicted? Convicted? Jailed? Paroled?
● If you weren’t paroled, how is it you’re out walking around?
● If the police seized your personal computer, which files would you most be worried about them finding?
● Can your life be ruined by the testimony of a child?
● What were the circumstances regarding your crime? Was there a big payoff?
● If so, where is the money now?


● What do you do for a living?
● How much money do you make?
● Can your job be outsourced?
● Were you ambitious at one time?
● If so, what the hell happened?
● How are you planning to retire, besides living off me/my [insert relationship here]?

Partner Preferences

● Why are you interested in me/my [insert relationship here]?
● Are you aware that [insert relationship here] spent two years with [insert embarrassing details of previous paramour here]?
● Are you aware that I/my [insert relationship here] cannot support you in your old age?
● Okay, see ya.


● Any weird diseases in your family?
● Any weird people in your family?
● Any history of mental illness, alcoholism, addiction, Civil War reenacting, voting Republican, excessive visits to Farmville?
● Were you adopted?
● If so, any weird stuff in that family?
● Any criminals in your family (either one)?
● If so, what were the circumstances regarding their crime?
● If there was a big payoff, where is the money now?


● What do you do in your spare time?
● Are there actually other people who do that too?
● Have you considered other hobbies besides Farmville?


● Do you have kids?
● Are they normal?
● If so, do they take after you or your former spouse?
● Do they still live with you?
● When are they planning to move out?
● Are they ever planning to move out?
● Okay, see ya.


About middleagecranky

The Middle-Age Cranky blog is written by baby boomer Howard Baldwin, who finds the world, while occasionally wondrous, increasingly aggravating.
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One Response to Questions You’d Really Like To Ask

  1. Faith says:

    These lists include just about everyone, and the exclude all possible partners.
    Which struck me as very amusing.

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