Note: This is the second of a two-part series. Click here for part one

Let’s say you’re 50 years of age or older. And let’s also say that you’re single and dating, or about to be single and interested in dating again. And finally, let’s also say that you’re unsure about how to evaluate and select someone who will be compatible, appropriate and wise for you, perhaps because you feel you haven’t done a good job selecting a partner wisely in your past.

Here is a continuation of the criteria I suggest you use in evaluating and choosing a potential intimate partner—for people 50 and over. If you can’t answer these questions confidently, you don’t know the other person well enough to make a decision about the future: Does s/he offer you partnership and teamwork? Two people working together for a common purpose, instead of your partner basically looking out only for him/herself. Do you feel included in your partner’s life and in his/her plans? Do you like her? This is a deeper question than it may appear to be at first glance. I’m not talking about feeling attracted to or sexually interested in her. I’m asking about something deeper.

Is he friendly to you? Helpful when you need to talk? A good listener? Compassionate? Kind? Respectful? Does she take care of you—or does she primarily expect to be taken care of? If anything terrible happened to you, could you rely on her to be there for you? Is he depressed? Volatile? Self-absorbed? Anxious? Compulsive? Screwed-up? If so, are you going to be able to handle this long-range? How does she behave at her worst? What’s it like to be with her when she’s sick, in a bad mood, depressed, discouraged, angry, revengeful, rageful, anxious, fearful? Are you (and others) mistrusted or treated poorly?

What are the conflicts between the two of you? How serious are they? Are these areas that could spell trouble down the road? Is your partner very hesitant to make a commitment? What experiences about commitment are each of you bringing into the relationship? Is he letting his heart get involved with you? Is he emotionally connected with you, or is he primarily with you for fun, sex or companionship? Does he share his inner self with you? Has he let you in?

How willing is she to blend with you? With your tastes, your lifestyle, your family and friends, the realities of your career or your income, your needs, your wants and your dreams? How good are his communication, conflict resolution, problem solving and negotiating skills? Is he able to discuss and resolve conflicts and differences as they arise—without destroying trust and love?

What substances or behaviors is she addicted to? Is this an addiction that could threaten the relationship? Do you play well together? How evenly matched are your interests—and in the ways the two of you have fun? How open are the two of you to creating new activities and interests together?

What are your partner’s attitudes about the frequency and importance of sex? How about the importance of fidelity? What priority does he put on your relationship verses the rest of his life? Are there any warning signs you notice that could be deal breakers later on?

Has your relationship turned cold and distant? Neil’s book Love, Sex, and Staying Warm can help you rekindle your passion.

Get My Book Today →
  • Did you find this article helpful? Share it with your friends!
  • Want more articles like this delivered to your inbox every week? Sign up here.
  • To make an appointment, call (303) 758-8777 or email [email protected].