Samara O'Shea, love columnist

Hi Samara,

I am 42 years old. Divorced twice, no children, 1 dog. Recently, I reconnected with my high school sweetheart. He is divorced with 2 children. We are madly in love once again and I think I want to spend the rest of my life with him.

The problem is that we reconnected once before in our late twenties and it didn’t work out and I was terribly hurt by him. I see many positive changes in him since we started seeing each other again. This is the third time around with him. I am wondering if we both needed to grow up before finding each other again or am I just fooling myself?

Any suggestions on how to approach this relationship this time around. I really want it to work.

Thank you,



Dear Third Time’s a Charm,

There’s a saying in the therapeutic community. It goes, “The best predictor of future behavior is past behavior.” While human beings are capable of change, we don’t do it easily or often. It’s easy to say, “I’ve changed!” It’s also easy to believe someone has changed because you want a relationship to work. The act of changing itself—not so easy. Also, time alone doesn’t usually instigate great change. Generally something has to happen—a spiritual experience, years of therapy, or even a tragedy—to inspire people to change.

All that said, I understand your desire to explore romantic possibilities with this man again and I encourage you to do so. This time around, however, please make a promise to yourself that you will take care of you. In other words, if his old hurtful behavior starts to surface, you will get out of Dodge.

As you get to know each other again, I recommend talking about what happened in your late twenties. Say, “I’m so happy that you’re back in my life, but I’m also afraid that what happened last time will happen again. How can we avoid it?” An ideal response on his part will reveal a new approach to the old situation. For example, “I promise to talk to you about what I’m feeling rather than let it stew” or “I will fight fair this time. I won’t blindly call you names when I’m angry.” If nothing else, he needs to acknowledge and express contrition for hurting you. If his response is vague—“It won’t happen again. I won’t let it.”—it’s a bad sign. If he’s dismissive and does not want to have the conversation at all—a very bad sign.

Keep in mind that no person can realistically promise “I’ll never hurt you.” We are all capable of hurting each other—whether we want to or not. The best we can do is approach difficult situations with compassion for all involved and a willingness to compromise.

I also recommend that the two of you take the Compatibility Quotient. This is a fun way to start some interesting conversations. This test was created by a psychiatrist named Glenn Wilson with the intention of determining whether or not couples will stay together. The theory behind his quotient is: The more each member of a couple have in common, the more likely they are to build lasting relationships. Research has shown that the Compatibility Quotient “is considered a valid test for measuring risk of divorcing in married couples.”

Of course, if this test reveals that you are not compatible it won’t be the end. No test—even if it were to be proven 100% accurate—would stop a couple experiencing the chemical high of infatuation from seeing each other. It is important, however, for both of you to know where the other stands on many of the topics presented in the test. Like I said, the conversation will be interesting.

I truly hope that the third time is charm for you and your high school sweetheart. But before I go: If you start to see his old behavior emerge and if it starts to take you down the same path it took you last time, please don’t wait to see how it ends. You already know. Excuse yourself from the relationship sooner than later. If his behavior has stayed the same, let your response be different.




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* The ideas and advice presented here are not a substitute for professional advice. Talk to your psychologist, counselor, physician or health care professional for situations that warrant further analysis.


Image courtesy of Marco Martini