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5 Reasons Longer Marriages Produce Red Flag Daters

09/03/2013 04:32 pm ET | Updated Nov 03, 2013

In the middle of enjoying a dinner with a male friend recently, all of a sudden the mood shifted when he asked in a terse tone, "So what's the longest relationship you've ever been in?"

"Under 10 years both times," I stammered, trying to make the first marriage appear longer than a couple years. He nodded his head knowingly, "I was married to one woman longer than both your marriages," he shot back proudly.

Ouch! It was like taking one right to the heart.

But as the dinner conversation (and drinks) progressed, we'd continued to discuss not only the length of our previous marriages, but what actually took place inside the relationship. He spoke freely about all his extramarital affairs, their periods of non-existent communication followed by bitter fighting, on and on.

Now I'll admit to my red flags: Married twice? Check. Longest relationship? A single digit eight years. Intimacy issues? Hey, maybe a few. But clearly some of his long-suffering details are waving something crimson as well. So why does conventional wisdom tell us those married longer are better relationship material just by default?

Should someone really get awarded safer bet status simply because they're proud about having "hung in there"?

Still obsessing about the dinner conversation a couple of days later, I recounted it to a girlfriend just approaching her fifth year hitched (I had apparently now taken to seeing imaginary lap numbers over the heads of my married friends). Even though I knew the answer was a resounding yes, I asked her to tell it to me straight: could my shorter track record be taken as a big red flag?

Like any good girlfriend she jumped quickly to my defense and even took it a step further: "Actually, I think someone who's been in a long marriage can be the worst kind of guy to date," she exclaimed. So in short order we quickly came up with plenty of red flags for those who proudly rack up years of mostly bad and ugly, and very little good:

1. Bad Habits: Do you want to play doubles with someone who has learned to play tennis with a bad swing and just keeps repeating that losing movement for years? What about marrying someone who couldn't talk to his or her spouse for 20?
2. Baggage: Longer marriages tend to produce more baggage. Unlike real baggage, the emotional kind rarely gets lost and usually travels with us to the next destination.
3. Ego: The last person you want to get involved with is one with a grandiosely deluded and "selfless" savior complex:
"I must stay with them because how could they survive without me?!"
4. Fear: I'm not happy with my spouse but what if I can't trade up? How will I be perceived if she does and I don't?
5. Greed: They stay simply for the money or because they don't want to split the assets.

So when I had another dinner with Mr. what's the longest relationship you've ever had, I posed the obvious question: "So why did you stay married so long?" Without missing a beat he replied, "I never would have gotten divorced," before bitterly adding, "I don't know why she had to breakup the family."

It seems to me the breakup, not to mention the festering resentments, can happen long before a marriage is officially over. When Michael Douglas admitted he should have split from his first wife much earlier it may not have been the most sensitive thing to say, but it nonetheless probably hit home for many.

Because when it's just a matter of doing the time isn't it kinder to opt for an early release to spare both people's happiness? After all, maybe the biggest red flag of all is someone waiting too long to wave the white flag of surrender.