November 3, 2023

3 Essential Skills we Need to Start Dating again after a Bad Breakup.

While coaching women through relationship endings and building a life they love, the most often question I get from them lately is “How will I know if I am ready to date?”

I am so impressed by women asking this! They are doing their “work” to heal. They have a newfound level of self-awareness. They are asking more questions internally rather than relying on the outside world to determine their reality.

Yet, entering the dating world seems to stump them like no other. Their confidence goes leaping out the window.

They’ve all heard the online dating horror dating stories, and then they see their old friend out with a new partner telling us how they found each other on the very first date.

My clients get pulled out of their newly built solid, centered self who just survived and who now are thriving in life after divorce just to be ushered into another uncharted world where they must face rejection, hurt, or disappointment all over again.

In other words, they see the next mountain they have to climb. And, understandably, they might not be up for the challenge just yet.

There is no doubt dating can feel overwhelming.

But here are three skills to practice on this next adventure as you balance optimism with realism while considering dating or in the dating process:

1. Be open to uncertainty; be open to new possibilities. People love to advise us we have to know what we are looking for in a partner to succeed in dating. However, dating can also be a search for what we want. Sometimes it is only by going through the experience do we understand what works for us. We don’t have to have it all figured out upfront before we start the process, which brings up feelings of uncertainty. Yet, the best thing about this vibe is it takes the pressure off so we can relax into the experiment of it all.

And guess what? Dating can also be fun. Meeting new people can be an adventure in itself without having to be attached to an outcome. We can learn how we relate to different personalities and be open to learning something outside of our comfort zone. We should search ourselves to see if we simply want to hurry up the process, get it over with, or settle down because underneath it all we are avoiding the uncomfortable feelings of insecurity, rejection, or lack of control.

A good question to ask is, “Am I willing to sit with this feeling and ride the wave of emotion before reaching for a person, food, online shopping, or any type of distraction as a way to avoid this feeling of uncertainty?” If you can practice what therapists call “urge surfing” to stay open to the process without having to control it, you are practicing a skill that will help you date successfully.

2. Have a grounding practice. If you can keep coming back to your internal strength in some kind of personal practice, such as meditation, prayer, mindful walking, meeting up with friends for coffee—anything that grounds you in your knowing that you are enough, whole, deserving of love just by being alive—you are prepared to ride the emotional roller coaster of dating as other people’s rejections won’t shake you so much.

While it may seem like conflicting advice when I say stay open but also stay grounded, if we get too unfettered in the process, we will lose our hard-earned balance. The goal is knowing how to come back to yourself, how not to abandon yourself, how to deliberately focus on your wholeness outside of a romantic relationship. This process is often a part of the work called strengthening your “psychological immune system.” Another simple question to ask is, “If I was already worthy/whole/happy in all areas of my life, what/who would I choose?”

3. Know thyself. Socrates’ advice still rings true today, “To know thyself is the beginning of wisdom.” Take all the personality tests you can find. Learn how you relate to different people. Try different activities and track your emotions—the feelings before and after an event (do you feel energized or depleted, and so on). Find out what you actually like versus what you do to keep loneliness at bay. Get to know yourself and all the places you feel harmony before offering yourself and your life to someone else. Find out what your deep wounds are and start relating to yourself as you would a little child pleading for you to love her.

Most emotional wounds fall into these categories: harm wounds, manipulation wounds, rejection wounds, and deficiency wounds. Researching how to heal your inner child or analyzing how your past traumas make you react today and replacing those unworthy beliefs may seem woo-woo for you, but it is a strategy that has huge payoffs in the dating world. The ultimate point is to be empowered by your values, knowing who you are, not defaulting to past patterns, and not focusing on the quest to fill your emptiness with someone else.

By learning what armor you have up, your heart softens so healthy love can come in. You no longer camouflage your pain and avoid true intimacy. Likewise, you confront your confirmation biases such as the belief all men or all women are a certain way. You see what level you are on and what level of partners you are seeking. This is a clear metric for matching with people. Clarity is freedom. Clarity helps you walk away from people who do not align with you. Clarity provides a system to rely on in tough situations where you may think this person is for you, but these mismatches are simply too obvious to ignore.

The reality of dating can bring up our vulnerabilities that take a lot more of our energy to work through. Asking yourself if you are emotionally steady enough to embrace this mountain is a great place to start. If you are up to the challenge but still feel a bit wobbly, which is completely natural, these strategies can help you find more of a solid footing. Staying open to the process releases us from any pressure to perform to get love. Discovering what is true for us, what gives our lives meaning, being in tune with our values, and knowing what excites us can offer us a sense of ease as we move onward and upward.


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