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How Do I Get it Right the 2nd or 3rd Time Around?

Divorce can do a number on more than just your bank account; it can deplete your self-confidence, making you second guess your entire approach to relationships – and this is a good thing! It’s always smart to really take your time after an important relationship ends, before dating and before becoming involved in another serious relationship. Why is this? Well, because the data speaks for itself. 50% of first marriages, 67% percent of second marriages, and 73% percent of third marriages fail.(1) Consider these numbers as you begin to contemplate your prospects for another committed relationship. When I work with individuals who are newly single, I help them to evaluate their own core values and the relationship they have with themselves. We do some exploration into who they currently are as people, and what their short-term and long-term goals are for themselves individually, as well as for the partnered version of themselves. What’s the difference? Plenty.

As an individual, you probably have ways in which you like to spend your time and your resources, as well as specific things that you’d like to accomplish during the time you’re here on earth. You also have a set of core values that you’ve developed throughout your life, that informs the lens through which you view yourself, your work, your hobbies, and your relationships. These core values address important realms of life, like family, faith, professions, politics, the environment, health, and well-being. Core values might even reflect deeper, more existential dynamics for you, like what is your life purpose and of all things, what matters most to you? Hard stuff to sometimes think about, made harder when you also consider your previous failed relationship. As a therapist, I find that it’s difficult for some people to talk about their own contribution to the demise of an important connection. It requires that you look at the influences that have shaped your persona and ask yourself tough questions about how you have been living or hiding from your own truth. It requires sitting in the discomfort of not knowing at first, then sitting in the discomfort of knowing! 


No one likes to sit in discomfort, and as people begin to recover from a failed relationship, there’s lots of discomfort. There also tends to be lots of anxiety about the possibility of not finding another viable partner to be with long-term. They start dating, find someone that they feel there is chemistry with, then quickly move into a more serious relational state, in effort to avoid the uncertainty of being alone. During this time, it’s helpful to be very clear on the lifestyle that you want to have, and to understand fully how this compares to the lifestyle that the person you’re dating wants to have. Do you both desire living 24/7 with each other, or does one or both of you really prefer some alone time in your own space? Do your interests and hobbies overlap well, or does it feel like one of you will be required to let go of their own personal interests or friends, in pursuit of joint activities? Do you have fun together and laugh often? How does the way that you like to spend time, resources, and energy compare with those of your intended? How does family fit in – specifically, children and/or aging parents? Are there travels you want to experience that are different from those of the person you’re dating? If so, how do you plan to address those? What about money? Who has what, and how do each of you see money being spent individually and together? What do holidays look like? What does sex look like, and are you both satisfied with the way in which you express yourselves sexually, and the frequency of your intimacy? How do your love languages compare? What does your current partner know about your family of origin? Have you shared fully about the reasons you believe that your previous relationship(s) failed? Have you fully disclosed any past traumas and how those have impacted your life? How do you each handle conflict? What kinds of things trigger each or you, and what happens when one of you gets triggered? These can be hard topics to dig into with a new love, but it’s imperative to do so, if you want to get it right the second or third time around.


Give yourself some grace, and some time, to become very clear on the life that you personally desire to live. There’s absolutely no shame in stating your position. Become curious about the same information for the person that you’re dating. Pay attention to patterns of behavior. People reveal their truths in subtle ways, and through actions more often than through words. DO NOT turn away from red flags or boundary violations. Read some good books on your own – and together – about relationships and how to foster connection and growth. Talk openly and share deeply with each other. Take it slow because the best things in life never need to be rushed.   



1.     Psychology Today. What is the Divorce Rate, Really?


Katey Villalon, LMFT, IRT

Call: 512-537-6339  Email:






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