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The Dating Paradox: Why You Haven’t Found the Right Person Yet

“I just haven’t found the right person yet.” Tamara sank back against the couch cushions, slumping her shoulders down. Her spirits were so heavy it seemed like she would sink into the ground if not for the floor beneath her.  “It is so hard,” she sighed. “There is just nobody out there.”

Tamara was expressing a common feeling that I hear from many singles in the dating scene. Whether you are a serial online dater, optimistically swipe right on dating apps, stalk successful shadchanim, or focus your efforts on prayer to the Almighty, chances are you have felt this way at some point. Why is it so hard to find the right person to marry?

Dating Can be a Catch 22

Although the answer might seem deceptively simple, it is easier said than done. The primary reason why it is so hard to find someone to marry is that dating involves a catch 22. A catch 22 is defined by the dictionary as “a dilemma or difficult circumstance from which there is no escape because of mutually conflicting or dependent conditions.” 

In the case of dating, one would like to escape dating by finding the right person to marry, but the process of choosing the right person to marry involves an essential step that is often emotionally difficult until one finds the right person to marry.

What is this essential step to identifying your potential life partner? In order to come to the realization that you would like to share the rest of your life living together with the person you are dating, you need to allow someone to get to know you. Small talk and chit chat are polite ways to start a first date, but you need to have deep conversation to make a genuine emotional connection with someone. You need to gradually share your true values, passions, and emotions in order to connect. 

As you allow your date to get to know you, he will likely follow your example and allow you to get to know him as well. This will help you both feel comfortable with each other. After several dates, you may be able to start to imagine what your life would be like living together. You may envision eating dinner together while discussing the highs and lows of your day, escaping “real life” to enjoy a relaxing vacation, navigating life’s daily ups and downs, and laughing at your own private jokes.

I share this approach with Tamara and she nods almost imperceptibly. Then, a thought bubbles up from deep inside her: “But, how can I let him get to know me when I do not know if I want to marry him?” “I do not want to become emotionally close to so many guys, only with the right one.”

I empathize with Tamara’s dilemma. She genuinely wishes to have an exclusive and unique relationship with her husband. It is difficult for her to imagine having many close relationships to guys, preceding that with her husband. She feels that if she lets herself go and develops an emotionally close relationship with a guy who she does not end up marrying it is as if she is cheating on her husband to be.

Therein lies the catch 22: You do not want to allow a guy to get to know “the real you” until you decide that you want to marry him, but you cannot decide that you want to marry him unless you allow him to get to know you. Another way to say this is: you do not want to invest the effort to develop a relationship with a guy before you know that your relationship will work out, but you cannot know that your relationship will work out unless you invest the effort to develop a relationship.

This phenomenon is true for both women and men.  I write this from the perspective of Tamara, and so I describe the catch 22 approach of many women in dating, but the catch 22 in dating affects both genders.

Escaping the Catch 22 of Dating

So is there any yellow brick road to navigate this paradox and create the home of your dreams?

There is a way out of this catch 22 of dating. It depends on you. You need to reject the core belief that traps you in the catch 22. In fact, you need to deliberately allow a guy to get to know you even though you have no idea if in the future you will want to marry one another. 

The following three steps are a brief overview of the way to approach dating as a journey of self-growth and self-expansion.

Step #1 – Gain Awareness

The first step is to become aware of this paradox. Recognize that having this approach will trap you into a cycle of “one and done” dates and “dead end” relationships. If you are loathe to invest in a relationship unless you know it is “worthwhile”, you will likely end up “going through the motions” on a lot of frustrating dates. 

Step #2 – Take an Interest in Your Date

Approach dating as an opportunity to get to know and appreciate another person. Your mission in dating, should you choose to accept it, is to delay judging the guy you are dating while you are on a date with him. Focus on the present instead of anticipating what your future holds. Your goal in the first few dates is not to determine if he is marriage material. Instead, try to take a genuine interest in him. Imagine you are an esteemed reporter for the major daily newspaper in your area and your assignment is to write an insightful profile about the guy you are dating. Ask open-ended questions to discover what makes him unique and what you can appreciate about him.

Step #3 – Allow Your Date to Get to Know You

An integral part of the process of dating is allowing your date to appreciate you. Your date can only appreciate you if you gradually share your personal beliefs, feelings and values with him. It may take effort for you to disclose deep aspects of yourself. If you are not used to making meaningful conversation on dates, you may need to invest time to reflect on your own about what makes you unique and what you would like your date to appreciate about you. Pre-thinking what you would like to share about yourself can make you feel more comfortable and at ease talking about yourself on dates.

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