Dear Dr. Chani,

A few months ago, Shari, a close friend of mine, set me up with her brother, Tani. I was honored that she would want to have me as her potential sister-in-law and was excited at the prospect of her brother being as caring and fun to be with as she is. Unfortunately, things did not work out as blissfully as I had hoped, and I would like to break up with him. It is so awkward and I dread the possibility of damaging my friendship.

Ever since Shari set me up with her brother she has been so excited. She tells everyone how she set us up and how perfect we are for each other. I am not sure if she is more excited about having me as a sister-in-law or about making a match. Either way, if I break up with her brother I know she will be disappointed.

I thought about explaining to her my reasons for breaking up with Tani, but it might not help. First of all, she might not agree with them and she might even try to convince me not to break up. Secondly, my reasons for breaking up are personal and I feel like it is betraying Tani to discuss them with his sister.

It is hard to explain why I want to break up with Tani. He has a lot of wonderful qualities and I am sure that he will make a great husband and father. The issue is that he is insecure and sometimes he is socially awkward. When we are on a date with just the two of us, it is not as apparent. Sometimes I notice it when he speaks hesitatingly to a waiter, but it is not a big deal. Yet, when we visited his family on a few occasions, I saw that he could not express his opinions easily and his siblings dominated him. It made me feel small and insecure to be there with him.

So you see that this is not the kind of reason I can share with Tani or Shari. I would feel bad telling Tani that I noticed his insecurities because it will probably make him feel even more insecure. And I cannot share it with Shari because she will feel insulted on her brother’s behalf.

What should I do?

Dear Batsheva,

It is very thoughtful and sensitive of you to carefully consider how to navigate your relationships with Tani and Shari. When your relationships with two people become intertwined it makes sense to be concerned that the way you deal with one person will affect your relationship with the other person. I am impressed that you are not considering moving forward with Tani in order to please Shari. Although it might sound like common sense, common sense is not always so common. Sometimes people prefer to keep the status quo in order to avoid rocking the boat in a relationship. Your clarity to break up even amidst the social pressure you feel is refreshing.

Since you are interested in ending your relationship with Tani, you are most concerned about how this will affect your relationship with Shari. Keep in mind that the way Shari reacts to your breaking up with Tani does not necessarily have to be based on your decision to break up with him as much as on how you go about it. There are several ways you can create a soft landing for ending your relationship with Tani.

Firstly, try to end your relationship with Tani on good terms and part ways as “friends.” When you speak to Tani, start by letting him know how much you appreciate him and enjoyed going out with him. Convey to him several very specific positive qualities that he has and how you noticed them in your relationship. For example, you might say something like, “I am really impressed with your thoughtfulness and attention to detail. I remember when I mentioned that I liked a certain kind of music, and you made sure to add it to your playlist and play it for me in the car the next time we went out.” Communicating what you appreciate about him and complimenting him will help Tani feel valued even though you are breaking up with him. He will recognize that your relationship was not “all bad” even though you are parting ways. On the contrary, you will encourage him to realize that you both gained a lot from dating one another.

You can then explain to him that you have been having doubts and you feel that even though he is so wonderful, something tells you that you are not right for each other. You might explain that it is a “personality” thing that is hard to describe. This is true—as you pointed out, it is difficult for you to describe to Tani what you notice about his insecurities. Finally, you can share with him that you would like to stay on good terms and you hope that you can be comfortable around each other in the future.

Try to be the one to tell Shani about your decision to break up. Ask Tani if he would allow you to be the one to share the news with Shari before he tells her. If she hears about the breakup from you, you will have the opportunity to shape her perspective on the situation. When you speak to Shani, start by expressing gratitude to her for setting you up, and especially for her valuing you enough to set you up with her brother. Let her know how much you enjoyed getting to know him and describe some of his specific wonderful qualities. You might also add that you can understand why she thought of the idea. You can then explain that, at the same time, you are not feeling like it is right for you personality-wise. Sometimes these things are hard to explain, but you feel it. You can also mention that you hope that this will not affect your relationship.

When you have done your best to be positive and appreciative while breaking up, the rest is up to the other people involved. Ultimately the way that Tani or Shari responds is not in your control. If you have invested thought and effort into handling the situation sensitively, trust that Shari will take your decision in stride. This is a test of your relationship. Hopefully by being sensitive to one another and trying to understand each other’s perspective your close friendship will not only survive but thrive from this experience.

Wishing you much success,

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 www.chanimaybruch.com