How to Escape the ‘Dating Catch 22’ (And Fall in Love Again)

by John P Morgan on 20 December 2010

He likes her. She’s smart and they have great conversation. He likes her voice and he likes looking at her. He enjoys reading her texts and when she calls, he likes hearing her voice. The sex is good and he thinks it could be even better if she weren’t holding back. He really likes her, but he just doesn’t know if she’s the one. He should as she seems to ‘tick all his boxes’, but still he’s not sure. Somehow he hasn’t fully connected with her yet.

She likes him. He makes her laugh. She has fun with him and loves the banter they have. When he calls, she always tries to find a quiet spot so she can listen and hear him clearly. Sex with him is really nice, but she’s doesn’t want to do it too much just yet. She will in time if things work out, but not yet. Not until she can really feel him. She wants to ask him what he’s feeling, but she doesn’t want to scare him away.

The man is waiting for the woman to open so that he can really know her before he decides to be with her.

He does this because he is afraid of giving up his freedom to the wrong woman. He wants love of course, but he doesn’t want to get trapped with someone who isn’t right for him.

The woman is waiting for the man to give so that she can feel his commitment before she opens herself to him.

She does this because she is afraid of being vulnerable to the wrong guy. She wants love, but she doesn’t want to get hurt by choosing someone who is not right for her.

In essence we have two people, attracted to and completely compatible with each other – maybe even perfect for each other – but who are both afraid to progress in the way that would give them exactly what they want.

This is what I call the Dating Catch 22.

The Fears of Love

You see; people generally fear two things when considering monogamous intimate love:

  1. Losing freedom
  2. Getting hurt

Losing freedom as a result of giving up space or being trapped in something that isn’t right or good enough is a fear of the mind – a masculine fear.

Although the fear of losing freedom arises in both men and women, being a masculine fear, it is usually the dominant fear for men.

Getting hurt as a result of opening up in a vulnerable way, feeling a deep love and then losing it, is a fear of the heart – a feminine fear.

Although the fear of getting hurt arises in both men and women as well, being a feminine fear, it is usually the dominant fear for women.

This difference in what is the dominant fear in a man versus a woman is an example of that which creates the polarity of attraction between the sexes. Of course all people may feel both fears to a unique degree, but for ease of explanation in this article I will use the most common situation; men fearing a loss of freedom and women fearing getting hurt.

Escaping the Dating Catch 22

To provide a woman with the feeling she needs, a man must fearlessly give to her, not through his words or his promises, but through his decisive actions and through his uninterrupted presence.

Only then will her fear of getting hurt wane. Only then will she feel him, open herself to him and open herself to being loved.

To provide a man with the knowing he needs, a woman must fearlessly open to him, not through her actions or sexually, but through her emotional vulnerability and through her uninhibited radiance.

Only then will his fear of losing freedom wane. Only then will he give himself to her and give himself to being loved.

You Go First

She is waiting for him to give before she opens and he is waiting for her to open before he gives. Thus there is really only one option:

You must go first.

If you afraid to open, then open you must.

If you are afraid to give, then give you must.

In the words of Susan Jeffers, you must “Feel the fear and do it anyway.”

This is the only way.

Stop Comparing to Apples to Apple Seeds

Each time you end a relationship, you take the deep knowing and feeling you had with your previous partner and you seek this experience with someone else.

You often forget that such deep knowing and feeling took months, or even years, to form through an intensifying of presence, commitment, opening and vulnerability.

By comparing to past relationships in this way, you are being unrealistic and unfair.

You may be wise to compare in outward things that make for a healthy and functional relationship, but in the realm of knowing and feeling someone – in the realm of love – you must stop comparing the fullness of an apple to what may still only be an apple seed.

Let Love Override

As you begin to fall for each other you may find yourself still making comparisons. In reverse to the above, you may actually be experiencing love, but it might not make sense to you because he or she is not who you thought you wanted.

In such a case it is best to let love wash away your imaginary list of wants.

It is best to allow yourself to forget these things, because if you do forget….then it wasn’t very important anyway.

Give It Time

Just because things don’t move quickly doesn’t mean it’s not good or right for you. It depends on how closed or attached to freedom your potential partner is.

Remember, these things are different for everyone and they also change throughout our lives. As you get to know each other and have emotional experiences together, your knowing and feeling adds up.

There might be something over the course of weeks or months that give you a better feeling about him – one you didn’t expect. There might be something that gives you a clearer knowing of her – one you were hoping to find.

Sometimes simply giving it more time can help bring you to the tipping point.

To that point when you say to yourself  “Yes, now I will open myself to him” or “Yes, now I will give myself to her”.

Reward Takes Risk

This is an obvious, but worth noting truth.

If you want to love you must be willing to risk the pain of losing it.

You cannot guarantee that you won’t get hurt. In fact, it is likely that you will experience pain through loss eventually. Loss in some fashion is inevitable, either by an ending of the relationship or an ending of life.

In the way that fully accepting death can take away the fear of dying, your full acceptance of the unavoidable risks of getting hurt in love will enable to you face the risk fearlessly.

Love Will Set You Free

If you end up in a relationship where you do not feel free, then it is either because it is not right for you or because you have not given enough of yourself. The solution in the first is obvious – you must end the relationship.

However, what does it mean to not feel free in a relationship because ‘you have not given enough’?
As we’ve discussed already, the masculine pathway out of the Dating Catch 22 is to give yourself to the other person.

By giving you may lose some outward or physical freedom, but in return you get to fall in love and as a result, you will feel more free.

And this is what matters isn’t it? How free you feel?

The truth is that in love, you transcend to a more pervasive freedom – a freedom that is born from within.

Know this deeply, give fully and love will set you free.

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{ 4 comments… read them below or add one }

1 Gita 27 December 2010 at 6:05 pm

so…when do you really know when is the right time to cross that line? by doing it too soon you are taking a risk of loosing that person if he/she is not ready for what you are looking for.


2 John P Morgan 28 December 2010 at 10:09 am

There is no right time Gita. In my mind there is only doing it or not doing it, the motivation for which must come from inside us. I think if we attempt to know when others are ready then we are not being true to ourselves or to them.


3 James Tripp 21 December 2010 at 6:51 pm

Nicely written John, with many good points.

I have seen that ‘Catch 22′ situation before, particularly when people get a bit older (past 30)… caution kicks in due to a reluctance to repeat past pain or due to having a ‘golden relationship’ in the past that everything gets compared to.

Not so sure about ‘love will set you free’ though. But then I am really not the romantic type.



4 John P Morgan 21 December 2010 at 7:04 pm

Good point about the age James. As for love/freedom, its not really romantic love. Think Turquoise Meme in Spiral Dynamics or compassion/enlightenment in Buddhist philosophy.


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