Dating - Blog

From Fantasy to Reality

Henry Cloud

I was doing a radio show one day when a young woman called in and said she didn’t know what to do with her boyfriend. When I asked what she meant, she said that she was struggling with whether to break up or to keep going, get more serious, and move toward marriage.

“Well, most times when people love each other and are thinking about marriage,” I said, “it is pretty clear to them; otherwise, why would they even be thinking of such a commitment? But for some reason, with you and him, it is not. What are those reasons?”

“Well ...” she started and hesitated. “There are some things that I just wish were different.”

“That’s pretty normal. No one person has everything we want,” I reasoned, wondering if she might be a little picky. “What are the things?”

“Well, he just doesn’t always pay attention to the relationship. It’s like I am the one who always is pushing for time together or to talk about things that we need to talk about. It seems that his hobbies and buddies are a bigger priority than I am. Like sometimes when we have a date, he might just keep playing basketball, and not even call, and then come over later and think that is going to be okay.”

“Also, he says he shares my values about physical limits, but he pushes me for sex and I don’t want to, but I keep having to say no over and over. And I am the one that has to push for having a spiritual life. ... I wish he was interested in spiritual things and just growing as a person.”

“Wow,” I said. “That’s a lot to be concerned about. So, what’s your question?”

“Well,” she said, “I want to know if I should break up with him or go forward toward getting engaged.”

“What have you tried to do about these things?” I asked.

“I have talked to him a lot,” she answered. “I have told him that I want to feel more important to him and that I want us to have a spiritual life together and that I want him to respect my physical limits.”

“That’s pretty good,” I told her. “And what happened?”

“He understands, he says. He agrees with me, saying that he wants the same things that I do. He is a really good guy,” she said with a little drop in her voice. “But then nothing really changes. I still feel like I am always the one who is trying to get things to be better.”

“Okay, question. If you have tried and tried and nothing has changed, and you are not happy, and the relationship isn’t working like you want a relationship to work, then why don’t you end it and move on? Why in God’s green earth are you thinking about even being serious with him, much less marriage? He is not interested in changing and being what you are looking for, so why don’t you get on down the road?”

And here it came, the moment that revealed what keeps a lot of young women stuck. “Because I love him,” she said.

In one way, I could not believe my ears. And yet I have heard it so many times from women that I could easily believe it. It was the answer I was expecting. Nevertheless, I asked, “What does that mean?”

“Well,” she went on, “I just love so many things about him. He is so good in so many ways. ...”

“Yeah,” I said, “but his character, and the way that he is in a relationship, makes all of those good things pretty unusable to you as well. You are really dissatisfied, but you have a big problem, and here it is: you are leading with your attachment to him.”

“What does that mean?” she asked.

“It means that what is driving your dilemma is that you have an attachment to him, instead of what is important to you: your values. Whenever we let our attachments drive us or guide us, we can get into all sorts of things that don’t work well. And that is what is happening here. You feel so attached to him that that is what is driving your thinking, instead of what you really want and value in a relationship.”

“But I really do love him,” she said.

“I know, but let me ask you something. If you were not dating anyone and I said to you, ‘Hey, Jill, I have somebody for you to go out with. I think you guys would be great for each other,’ what would you say?”

“Well,” she said, “I would want to know what he is like. I would ask you more.”

“Fine,” I said. “He is a fun guy, but he will use you for sex and he really won’t pay attention to what you want. He will ignore you when it is convenient for him to do so, like going to play basketball with his friends instead of keeping his commitment with you, but he will call you later to see if you want his leftover time. And when you want to have a spiritual life, forget doing that with him. He is not interested, and you are on your own there. But don’t worry, I am sure you will love him a lot and maybe even want to marry him.”

The phone was silent for a moment. “Well, I don’t think I would be that interested,” she said. “Who would want that?”

“Exactly,” I said. “That is because if you have not met him, you are leading with your values and not with your attachment. Since you are not attached to this hypothetical guy, you have no problem seeing it. But with Jason you do, because your attachment gets in the way. You are leading from the wrong place, like an addict who knows that getting high is destroying her, but she is so attached to the drug that she can’t give it up.”

“I think I know what I have to do,” she said. “This is not what I want in my life. But how do I do it?”

“Let your values drive you,” I said. “Say to him exactly what you just said to me: ‘Jason, let me tell you what is important to me and what I am looking for. I want someone who makes a relationship with me a priority and where I feel wanted. I want someone who not only says he shares my values but actually lives them out and respects my wishes when I do. I want someone who is into spiritual growth and improving as a person and who is responsible in life. I want someone who keeps his promises. That is what I am looking for in a guy.

“ ‘Right now you are not that person. I want you to be that person—I really do. But you are not. If you become that person someday, you can call me, though I don’t know if I will be there or not. Perhaps by then I will have already found him. But that is what I am looking for and I am not going to settle for less. So we have to break up.’

“If you say that,” I said, “then you are truly leading with your values and not letting your attachment to him get in the way. Then you let go and move on, period. No looking back.”

She told me she got it, we hung up, and I hoped she did get it. I will probably never know. But I do know, from working with a lot of women, that if she doesn’t get it, she is in for a world of hurt. Why is this, and how can you avoid this kind of pain in your own dating relationships? Let’s look at some of the biggest causes of “date diseases” that take women places where they don’t want to go.


This was Jill’s problem. As I told her, she had not gotten clear about her values and what mattered to her before she got attached to someone. So she found herself deeply attached to Jason and yet continually disappointed. But she was letting how she felt for him keep her stuck. Or at least sort of.

In reality, she was letting half of what she felt keep her stuck. She was letting the half of her that loved him and wanted him keep her in the relationship. But she was ignoring the other half of her, the part that was hurt, disappointed, and left wanting more. This huge part of reality was a sign to her that things that matter were not present in the relationship—things that she really wanted in someone she was going to be serious with and potentially end up with for the rest of her life. Those are the things that come from our values.

To value something means to “assign great weight” to it. The things we value are weighty issues. They should command our attention more than anything else. And they should dictate whether or not someone gets through the gate to our heart. It is easy to have feelings for someone you are attracted to, but if the things you truly value are not present in him, then you will find that those things render all the things you find attractive about him spoiled in the end.

You will not be able to enjoy them, or even have them sometimes, because the things that make a relationship truly work are not present.

So, before you even meet him, ask yourself what your nonnegotiable things are. I like the way David expressed some of his in Psalm 101. He said that things like honesty, faithfulness, and purity were important and that he would have nothing to do with people who did not possess those qualities. I wish all single women everywhere would date that way! Even if David liked someone, or that person possessed things that would be attractive to him, he would not trust such a person or give his heart away without
the essential values being present. Have you thought about what those are for you? Here are some things to think about, and you can add your own as well:

  • The ability to connect emotionally, to empathize, and to be present with you
  • The ability to give freedom and not control you
  • The ability to be real, and allow you to be real, instead of requiring perfection or having impossible standards
  • The ability to be equals and show mutual respect
  • Having a spiritual life of his own that you respect
  • Honesty, faithfulness, dependability, sexual purity, integrity, responsibility, financial responsibility, compassion, forgiveness

These are the kinds of things that make relationships work in the long run. You will find many people you can be attracted to for a variety of reasons, some good and some not so good. But when you find yourself attracted, make sure that before you let your heart get involved, or let it stay involved, you make sure they possess the things you value most. Know what you want before you know who you want.


When I have talked to women like Jill who are not finding what they want, or who are settling for what they don’t want, there is a common theme: they are trying to fill something inside them with that relationship. There is some sort of loneliness or a need to find validation of themselves—or even meaning—in a relationship with a guy. Many women give men way too much power to prove to themselves that they are lovable and desirable and even to make life worth living. They feel as if life is somehow not complete if they are not in a relationship with a guy.

When this happens, it makes letting go of someone, or not getting involved with someone, more difficult. The mantra seems to be that a not-so-good relationship is better than no relationship at all. But are those the only options?

The answer is that women who attract the best men, and who pick the best men, are women whose lives are complete without being in a serious relationship. “Aw, come on,” you might be saying. “What a killjoy!” No, I don’t mean to be, as I want a good significant relationship for you as well. That is a wonderful thing to be in. But the truth is that if you need it to be happy or to be complete, then you are not ready for one. Only a person who does not need the other person to be whole is whole enough to make a relationship work and to attract a truly whole person also. So make sure of a few things:

  • Make sure that you are in a good, closeknit group of friends, male and female, so that all your relational needs are being met. If this is true, you have intimacy, connectedness, and support and you are not lonely at all. You will not be so needy that you “can’t live without him,” if he is not the right one. You will be perfectly happy in your community.
  • Make sure that you are growing spiritually. Many times people try to fill a spiritual vacuum with a romantic attachment. Since romance itself is something of a transcendent experience, it can masquerade as having the ability to fill parts of your heart and soul that only God can fill. If you are growing close to Him and being fulfilled in your spirit, you will not ask a relationship to do something for you that it cannot. And you will be able to trust God to bring the right person along.
  • Make sure that you are growing as a person and doing fulfilling things. Often someone dates poorly because life feels empty. She tries to fill an empty life with a person, trying to gain meaning from a relationship, when the real problem is a real lack of purpose and fulfillment. Find out what your talents and gifts are and develop them. Step out and grow in new areas and activities, and find your real passion and pursue it. When your life is full with purpose and with pursuing the gifts that God has given you, you won’t ask romance to fill an empty life. You will be so busy and fulfilled that it is going to take a really special guy to get you to make room for him in your wonderful life!


I hear it all the time. Women start dating someone, quickly get interested in him, and then stop dating everyone else. Then, when the relationship does not pan out, they repeat the cycle. They start dating again and fi nd one guy and get serious. When that relationship does not work, same thing again. As a result, they have a string of exclusive relationships but not much experience in dating a lot of people casually.

If you read my book How to Find a Date Worth Keeping (Zondervan, 2005), you will see what a big proponent I am of dating a lot of people. Dating is not about “finding the one”; it is about having fun and getting to know different kinds of people. If you have not dated a lot, then chances are that you really don’t even know what you want or need. You may be stuck in looking for some “type” and not getting to know real people and through that process getting to know what kind of “type” you really need.

You should get more involved with someone only when he stands out in the crowd. It is easy to stand out in a crowd of one! Anyone can look good. You need to know what a lot of different kinds of people and experiences are like to chose well. How do you know you want the athletic type if you have never dated a brain? Get out there and discover the world.


It may be that the suggestion above seems out of reach, because you are not getting the chance to have a lot of dates. Is that true? If it is, then ask yourself and your close friends why. Why is it that you are not dating much or meeting many good guys? Is it your schedule? Is it your traffi c pattern that keeps you around the same few people over and over? Maybe it is time to get out and try some new things or new circles. If you keep doing the same thing over and over, expecting different results, chances are that you will be dissatisfied.

Or are there more internal issues that are keeping you from dating? Are you not giving off signals that you are open? Are you not talking to guys at social gatherings or other places? Are you afraid of rejection or self-conscious in some way? Have you been hurt, and is that still affecting you? Whatever it is, be open to the fact that you may be doing some things that are reducing your chances of having dates, and do something about those issues. Talk to your friends or to a counselor about whatever that is. I can tell you that I see women all the time overcoming those kinds of things and turning a stagnant dating life around. God can heal those things in your life, but you have to ask Him to help you and get with someone else who can provide that kind of help.


It is the lone sheep who gets grabbed by the wolf. But if you stay in the pack, you will find safety. How does this turn into a dating mistake? Often when women begin dating someone they like, they drop out of life, in terms of their community and friends who ground them. So they gradually lose their greatest source of protection, feedback, and strength. As a result, they can fi nd themselves deeper in a not-so-great situation than they would want to be and can find themselves unable to get out.

Stay connected to your friends throughout your dating experience. Talk to them about your dates and let them evaluate your dates for you. Get their feedback on how a guy treats you or what his issues are. Listen to them, for they might see things your smitten eyes have missed. Use their support to be able to deal with those things. I wish I had a nickel for every woman I have heard say, “I wish I had listened to my friends.” Your friends are your best protection. You might hear them say, “What are you thinking?!” If they do, then listen.

Also, date in the context of your friends. Do things with them on your dates so that they can meet the guy and see him directly. That is where your life is, and he must integrate into your life. If he will not, or if he is not interested in getting to know the people you love, then something is wrong. Let that be a red flag. Remember, your community is your family. If he is interested in doing things only in his own circles, that is not a good sign. He must come your way, too.


Often, unfulfilling relationships are in some way a repeat or a symptom of family-of-origin issues. The classic example is the woman who is attracted to emotionally unavailable men and never realizes that she learned how to do that from an emotionally unavailable father. She is still longing for the detached dad to finally love her, and she keeps on finding him in the guys she dates, always striving to get someone who is incapable of love to somehow wake up and “get it.”

It could be other patterns as well. Sometimes when someone grows up in a family where one or both parents were perfectionists or were critical, for example, she finds herself drawn to people who can’t ever be pleased. Or she falls into other attractions, such as being drawn to addicts or self-centered people who are living out the ways that Mom or Dad did. What is happening is that she is repeating relational patterns she learned growing up, and she is failing to connect the dots. God designed us to learn our relational patterns in our families, and we do. If it goes well, we learn healthy patterns, and if there is dysfunction, we learn that as well.

Make sure that you have done what the Bible teaches and have grown past the generational patterns that have been handed down. If necessary, get counseling. Talk to your good friends about your patterns and see how you may be repeating some old hurts. Get involved in a new family, your community of friends, or your spiritual community, where you can learn new ways to relate and rise above the ones that are not working. Learn what you did not learn in your family of origin, and then you can find it in your dating life.


I talk to women all the time who are disappointed with the spirituality of the guys they are dating. But they did not think about that in the beginning. They just got serious about someone and then found they were driving the spiritual train, having to nag him into keeping up. Remember, if your spiritual life is important to you, then you are the one motivating that, not someone else, right? No one is making you care about your growth. In the same way, you have to find a guy who is selfmotivated as well. If he is not, you are just going to get frustrated trying to get him to be different. That does not mean you can’t expose him to your spiritual community, and things like that, and see if he wants to grow—that’s great. But to have to push someone is going to get old in the end.

Get to know guys who are at the same level of motivation and growth that you are, and then you will have spiritual compatibility. You will love growing together and you won’t be unequally yoked in your dating experience. Of course, you will probably go out with all guys at many different spiritual levels, but if you are going to get attached or serious, then you have to be more discerning and look for spiritual compatibility after some amount of time.


We know that women fantasize about relationships. That’s not all bad, for you fantasy comes from your deepest desires. And we know that it is God’s desire that your deepest desires are met. He even says that when they are not, it can make your heart sick: “A desire accomplished is sweet to the soul, but hope deferred makes the heart sick.” (Proverbs 13:12) So, when you dream about having a good relationship, that can be a good thing.

But for a good relationship to materialize, the fantasy or the dream has to be rooted in reality. You have to be dreaming for the things that turn those dreams into real, tangible relationships. You can’t, like Jill, be dreaming for someone without character and values to provide a good relationship for you. If you are, then you are just dreaming.

For dreams to become reality—and they can—they have to be rooted in real things that make them real. Get your dating life rooted in a deep relationship with God, deep relationships with friends who love you and give you feedback, deep and important values, and a fulfilling life of expressing your talents. As you are doing those things, you will be a grounded person who can find the kind of person who is like you and with whom your best fantasies can find themselves in the real world.

DR. HENRY CLOUD is a clinical psychologist and bestselling author or co-author of over eighteen books, including How to Get a Date Worth Keeping and Boundaries in Dating. He also conducts seminars across the country and co-hosts a radio program called New Life Live. He’s the president of Cloud-Townsend Resources.

Chapter excerpt taken from “Fantasy” (CruPress).

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