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On Life and Love after 50, by Tom Blake
On Life and Love after 50, by Tom Blake

By Tom Blake

In 25 years of writing about senior dating, there’s one topic I’ve been asked about at least 200 times, and I feel particularly qualified to address it. The topic surfaced again last week, when a single woman, age 69, emailed this question:

“I’ve had three ‘failed marriages.’ Should three divorces matter to the men I meet? Might they be a deal-breaker? Turnoff? Red flag? Or, (hopefully) a non-issue? Should I disclose the number in my online dating profile?”

Why do I feel qualified to tackle that topic? Because when I met my partner, Greta, 21 years ago, I’d been married three times, and so had she.

My response to the woman: “There’s no automatic answer; here are 11 “multiple marriages” factors to consider:

  1. What is your dating goal? To marry again? Or, simply to meet a nice man friend with whom you can have a committed relationship? Your answer could determine how a potential mate might feel about your three marriages.
  2. What is his dating goal? If he wants marriage, your three marriages may be a red flag to him.
  3. However, if he doesn’t want marriage—most older men don’t—and only seeks a committed relationship, your three marriages may be a non-issue with him.
  4. If you meet a nice man, you’ll want to know how many marriages he’s had, how long they lasted and why they ended. You wouldn’t want to become involved with someone who has a history of terrible marriages or relationships. You need to protect yourself.
  5. Or maybe he never married. If not, why didn’t he? Was he unable or unwilling to commit?
  6. If a person is widowed, he or she had no control over losing that spouse. Should that loss count in the number of previous marriages tally? Of course not. (However, if the person had four or more marriages, and each spouse died under suspicious circumstances, that would be a red flag).
  7. You said you’ve had three “failed marriages.” I don’t like the term “failed.” Most marriages were the right thing to do at that time. But as years pass, people change. and marriages can fade. Does that make your marriages failures? No. They just didn’t last forever, although they were likely successful for a while.
  8. Often, a marriage that ends in divorce turns out to be a blessing in disguise, although at the time of the breakup, it didn’t seem that way. Hence, your three marriages that ended may have been blessings.
  9. Before a new relationship turns serious, the number of prior marriages isn’t as important as the disclosure of them. But, on your online dating profile, simply state, “Divorced.” Also, people who’ve remarried had the courage and were willing to take the risk and try again, which are positives.
  10. Understanding what happened in your three marriages can help you build a more solid relationship the next time around.
  11. There are many other factors to consider besides the number of former marriages; a potential mate’s attitude, happiness and outlook on life are significant. Most importantly, how would he treat you?”

For Greta and me, having the same number of marriages was one of the things we revealed when sharing information on our first date; so for us, “multiple marriages” was something we had in common.
And despite three marriages each, we’ve enjoyed the best relationship we could ever have hoped for. We live together but aren’t married.
In senior dating, should the number of marriages matter? I don’t think so. But when the number reaches four, it’s time to scratch your head; five or more, well, the issue gets cloudy. Still, don’t call them “failed marriages.” Simply call them “marriages that ended.”

Tom Blake is a Dana Point resident and a former Dana Point businessman who has authored several books on middle-aged dating. See his websites; and To receive Tom’s weekly online newsletter, sign up at Email:

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