When do you know whether to start a new relationship?

Gillian Asked:

When do you know whether you are ready for a serious relationship after the break-up of a 33-year marriage?

~ Gillian from Stuttgart

Advisor Jen answers: Gillian, this is a difficult question to answer. I feel for your situation because 33 years is a very long time, indeed. It represents a major investment of emotions, and the sharing of the most intimate aspects of life’s journey. It is impossible to fully sever all connections to the good and bad of one’s past. At the same time, the human spirit calls us to renewal, and the time comes when we must move on and open ourselves to new love and experience. But how do you tell when you are ready? I think one knows intuitively when it is time. But we have a way of letting ourselves know when things are moving too quickly too. I would say that if you have an inkling that it is time, you should really decide how to handle things before you meet someone. Try setting a time-frame to your dating so that you don’t move too quickly. For example, you might want to ensure that you and a new date do a few things that you each enjoy – hiking, site-seeing, washing cars together, or something else before getting physical. The key is to do some normal things that aren’t necessarily romantic or exhilarating. You don’t want to lose perspective on whether you really find this person interesting. If the prospect of persuing a new relationship in a relaxed and confident way is too challenging for you, I think that you should conclude that you are not ready for a new relationship. But, eventually you will be. Oh – and if your friend isn’t supportive of your stance, move on.


  1. I’d say it’s easy to tell. After 33 years, everybody is ready for a new relationship.

    • As usual, Phil brings his unhealthy negativity to mediocreadvice.com I think that Jen’s advice is generally on, but Gillian, I think there is a time when leaping for love is the best way to go. I mean, stay strong, but let someone love you when your instincts tell you to. And if you make a mistake, you will recover. I sense that you are a compassionate person. Don’t forget to be compassionate with yourself, too. You deserve it!

      • I have to agree with the ladies on this one. Be passionate but wise. As President Reagan said when questioned about trust of the Soviets during the Iceland talks with Gorbechev, “trust, but verify”.

        • I don’t understand how nuclear disarmament talks relate to Gillian’s question.

          • You guys all missed the point. Gillian only asked how you know when you are ready. She wasn’t asking for advice on how to act. The advice you gave is truly mediocre.

  2. If the sex is good, then you are ready for a new relationship. Of course, that means having sex before the relationship begins.

  3. I feel it in my fingers, I feel it in my toes.
    Well love is all around me, and so the feeling grows.
    It´s written on the wind, it´s everywhere I go.
    So if you really love me, come on and let it show.

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