Dear Dr. Chani,

I have been dating for many years now, and I have not felt comfortable with most of the guys I have met. Recently, someone asked me if there was ever someone I liked. The truth is that four years ago, I dated a guy that I would see again in a heartbeat. I’m just not sure if he would be willing to go out with me again.

The guy—let’s call him Ari—was what I am looking for in many ways. He was easy to talk to, smart, and a go-getter. In the beginning, we hit it off right away. After three dates, he talked about wanting to introduce me to his parents. I thought that we would be engaged within a short time. But then, from out of nowhere, he broke up with me.

I think it might have been because he misunderstood something that I said. We were driving and we passed by an area with lots of mansions, and I said that I had always dreamed of living in a house like one of those. I wonder if he thought that I am hung up on materialism and superficiality. I am really not at all like that. I grew up in a simple, three-bedroom house, and I would not mind having a down-to-earth, frugal lifestyle. But I really never had a chance to explain myself.

Over the first two years after we dated, several people tried to set me up with Ari again. Each time, Ari said no. Eventually, I gave up trying to go out with him and put him out of my mind.

Now I am wondering if it makes sense to ask him again. I have heard that he is still dating. Maybe he has changed his mind and would be willing to give me a chance. But what if he is totally not interested in me? I would feel so humiliated if he thought that I was chasing him. What should I do?

Sincerely,

Hopeful

Dear Hopeful,

You are describing a tough situation. You are drawn to date a specific person. Yet, you are concerned that if you express your interest it will leave you seeming both needy and like you are pursuing him.

The situation that you are in highlights one of the most difficult parts of dating. On the way toward finding a lasting, deep and meaningful relationship, there is often the need to take a risk. When you go out on a date, agree to go out again or admit that you really like someone, you take a risk that your positive feelings will not be reciprocated. You need to be willing to take this risk to enable you to eventually develop a healthy and loving relationship with someone who will become your future spouse.

If you feel that there might be potential for you to develop a relationship with Ari, it sounds like it is worthwhile for you to take a risk and try to communicate your desire to see him again. Yet it is important for you to reduce the potential of feeling emotionally vulnerable. Here you can walk a delicate and significant tightrope. When you take a step forward in a relationship, think of yourself as being “interested, but undecided.” This is not just a protective stance, but it is the most true approach to your situation. Even though you are interested, it does not mean that you are ready to make a commitment. It does not mean that you will be devastated if the relationship does not work out. It just means that you appreciate aspects of the person. When you let a person know you are interested, you are, in essence, giving him a compliment. You are saying, “I appreciate something about you. I am interested in discovering more about you.” If the person does not want to continue getting to know you, it is his loss.

How do you convey this balance between being interested but still being undecided? The first part is to internalize it yourself. For example, regarding Ari, based on the history you are describing, it sounds like there are reasons that you might build up the idea of going out with Ari again too much. If you have dated for a while and had little success, chances are that your positive experience with Ari grew out of proportion in your mind. You built it up to such an extent that it almost seems larger than life. It might be important to keep yourself grounded and to realize that there is potential with Ari, but you are still exploring. Avoid planning and daydreaming about your wedding at the moment. Remember, you are “interested but undecided.”

In addition, you can have this approach conveyed to Ari. Depending on your culture, either find someone who can be your advocate to suggest the idea to Ari or approach him yourself. The main idea that you or your advocate should convey is that you enjoyed dating Ari in the past and you are interested in dating him again. Let Ari know that in the limited time that you went out with him you saw potential and would like to pursue it further. You can add that you understand that some things might have gone awry the first time, but time has passed. Aside from possible misunderstandings that happened the first time, you are probably both somewhat different than you were several years ago. Speak straight and to the point. Express that it is worthwhile to have another opportunity to get to know each other better.

Asking an advocate to speak to Ari on your behalf has an added benefit that this person can remind Ari about all of your wonderful qualities. Pay attention to what advocate you choose. Sometimes an advocate merely makes a suggestion or describes you to someone. This is not enough. It can give an impression that Ari is being asked to do you a favor by going out with you. Therefore, try to choose an advocate who knows you well enough to sing your praises. You want someone who will communicate to Ari why it is in his interest to go out again with you!

Whether or not Ari agrees to go out with you this time, it is worthwhile for you to explore this possibility. By internalizing the “interested, but undecided” approach for yourself, you will, in any event, build your resilience that will allow you to take the necessary risks in dating to develop the wonderful relationship you dream about.

Wishing you much success,

Chani

Chani Maybruch is a social psychologist and relationship coach specializing in teaching emotional connection and communication skills for over two decades. She coaches individuals and couples, teaches courses on how to become a master of relationships and provides free relationship resources at chanimaybruch.com. Learn a step-by-step method to improve your ability to emotionally connect with her new online course: The RELATE Technique™—Seven Steps to Emotionally Connect Through Conversation. Reach out to her at [email protected]