Dear Dr. Chani,

I have been dating for about four years and I noticed that I have a strange pattern. It just happened again with a guy I had been dating for a month. Let’s call him Danny. During the time that we were dating, I felt nothing for him. We had pleasant dates with fine conversations, but nothing special. It would have made no difference to me if I never saw him again after each date. Since I had no specific reason to quit, I kept going out. Yet, when I finally ran out of gas, I broke up with Danny. Ironically, that is when I began to feel positive feelings for him. It is so frustrating and confusing.

One of the things I remember about my break-up conversation with Danny is that it was the first time that we opened up to each other. I expressed to him how I think we are different, describing my views and my personality. Danny took what I was saying really well. Instead of being defensive, he really listened to me. He shared that he understands we have our differences but he thinks we could balance each other out. It was hard for me to reverse course in the moment since I had already made up my mind to break up with him and move on. So I ended up breaking up even though I was beginning to doubt my reasons.

Now that we are no longer in a relationship, I feel a huge pit in my stomach signaling to me that I made a mistake. Why is it that I tend to regret my decision after I break up with someone? Is this normal? Should I consider getting back together with Danny? I feel like if I did not have this pattern I could have already been married several times. Please let me know what you think.

Thank you so much,

Humpty Dumpty, the Break-Up Expert

Dear Humpty,

Your observations and questions about your pattern in dating make a lot of sense. Dating might be one of the most misunderstood areas in human relations. People sometimes think that when they find the “right person,” they will naturally be drawn to each other and their conversations will flow freely. That approach to dating can be reinforced by their reliance on the concept of “bashert,” the idea that there is a soul-mate who is meant to be your ideal and predestined marriage partner. There is an implicit assumption that people will automatically be pulled to their bashert. Some people might include a belief in love at first sight in their dating. That idea is likely a myth that has its roots in popular culture rather than in true dating experiences. In reality, dating is a situation where two people put effort into having conversations to potentially create a relationship. That means that it is important for the people who are dating to converse about themselves and share meaningful aspects of who they are, such as their opinions, values and goals. Their discussions should also usually include some information about their background, past experiences, family and friends.

Nevertheless, it is common for people to feel awkward talking about themselves and things close to their hearts. Instead, they feel more comfortable having light conversations about current events, or their day-to-day happenings, without giving the person they are dating a real insight into who they are.

There are several reasons why people might have this discomfort and hold back from allowing their dating partner to really get to know them. Firstly, some people feel awkward sharing information about themselves and their lives with a stranger. They wonder how long their dating relationship with this person will be, so they are cautious about expressing too much and then having no connection to the person afterward. Secondly, some are concerned about sharing too much too soon. They feel that until the person really knows them, they are unable to share that much about themselves. Thirdly, some are concerned about being judged by the other person. If the person really knows who they are, they might not like them and want to continue to date them. Instead, they carefully select things to share with the other person that portray how they want the other person to see them.

Although these reasons might make sense, they stand in the way of a couple allowing a real relationship between them to develop. Such feelings can cause someone to hold in her emotions and inhibit talking about herself until later on in a dating relationship. It sounds like this is at least partly what contributes to your dating pattern of beginning to feel emotionally connected to a person you are dating during a break up conversation. You hold off when there is still uncertainty about how you feel about your dating partner and how your relationship will progress. When that concern is alleviated, ironically as you are about to break up, you feel more comfortable disclosing personal information about yourself.

How can those concerns be tackled? One approach is to look at dating like peeling an onion. If you leave the skin on an onion, you will not sense its flavor. On the other hand, if you cut it straight down the middle, you will end up crying. Dating is the same way. If you do not share yourself and allow meaningful conversations, you will find that your dating relationships peter out. Yet, on the other hand, if you begin a dating relationship with full self-disclosure and vulnerabilities, your dating partner will have no context of who you are and will not feel comfortable or be able to appreciate you. Instead, think of some basic personal and meaningful things about yourself that you can share on each date. Allow what you share about yourself to progress from general information that you would share with most people to more personal information that you do not discuss so readily.

For example, on a first date, you can share what your job is and how you like it. Make sure to add personal aspects to that conversation, such as what led you to pick that profession and what you enjoy about it. Notice that although those are personal topics, they are not necessarily private. You could share them with someone you sit next to at a wedding or on an airplane. On a subsequent date, you might feel comfortable sharing how you feel about selecting that profession as opposed to another one that you were considering, or describing some of your future career plans that may be different from your current job. On a further date, you might share some of the downsides of your job and specific challenges you have faced. You might also include regrets and second thoughts you have. Although all of these ideas center around your job, you are sharing gradually. By doing that, you are allowing your conversations to develop through time and discussing different aspects of your job in layers.

You can include other aspects of your life in your conversations, such as your pastimes, educational experiences and your family, and share about them in progressively deeper layers. Over time, you will find that your dating conversations allow you to share things about yourself and your life in a way that is gradual and connective.

It sounds like you were holding back from sharing during dating but also realized its importance. You have been going to extremes, from not sharing at all to sharing intensely, when it is too late. It can be helpful to gradually share about yourself and who you are. This way, your dating conversations will develop in stages and nurture your relationship as it grows.

You may want to revisit your relationship with Danny and strive to gradually allow him to get to know you. Give it some time and see where it goes. It sounds like Danny was a good listener and accepting of you. These are great qualities that can help build a solid foundation for a healthy relationship. Your initial conversations were superficial and not connective. Another opportunity to date each other, with a specific objective of progressively sharing about yourself, might be very helpful to both of you.

Wishing you much success,

Chani

Dr. 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, and teaches online courses to help you create your ideal relationship. Get free relationship resources and contact her at chanimaybruch.com.