Dear Dr. Chani,

There is a guy who lives in my neighborhood who I would love to date. There is one problem—he does not seem interested in me. Or maybe he is.

Let’s call him Zack. Zack and I have been friends for a few years. I often host him for Shabbat meals together with other people. We help each other out a lot. I lend him my car when he is stuck and he sometimes runs errands for me. We have common interests and get along really well. Sometimes we even give each other dating advice and support. There are times when we talk for hours and we really connect.

Yet, for some reason, Zack has never asked me out.

A few months ago, I asked a mutual friend to ask Zack if he was interested in dating me. He said he values our friendship but does not think about me in that way. Zack has a very specific idea of the woman he would like to marry and I do not fit that image. I was disappointed but not surprised.

My question is if there is hope for me with Zack. Even though he claims to have a clear idea of the person he would like to marry, I get a feeling that he is confused and unrealistic. We have a stable and enjoyable relationship. Would he not eventually realize that this is the best foundation for a happy marriage?

Do you think there is something that I can do to win him over? Maybe if I stop hanging out with him, he will appreciate me more? What do you think?

Sincerely,

Hope

Dear Hope,

Right now you are enjoying a warm and comfortable relationship with a man you think is wonderful. There are a lot of benefits to holding on to this relationship. You enjoy his companionship. You help each other out. You feel appreciated and valued. Yet this all works up to a certain point. When you explore the possibility of developing your relationship with Zack into dating and marriage, he turns you down. I can imagine that it is very confusing, and probably painful, too.

Even though your ego is bruised, you have not given up hope. You like Zack enough to give him a second chance. After all, he has chosen to be such good friends with you. It sounds like the situation is hopeful. You would imagine that it would not take him much of a leap for him to eventually want to date you, and perhaps marry you.

Unfortunately, it seems more probable you are setting yourself up for an emotional rollercoaster of hope and disappointment. While it is possible that Zack might eventually be interested in dating you, you should not wait around for him to figure this out. Take him at his word that he enjoys your friendship, but he is not interested in dating or marrying you. Even if he really is uncertain and wavering about dating you, your persistence and waiting will diminish you in his eyes, which will make your future together even less likely. It can also take an emotional toll on you and affect your happiness and sense of self. Your investment risk is not worth the possible return.

When it comes to relationships, there can be a lot more going on than meets the eye. Zack might truly enjoy your friendship, but he may also have reasons for not dating you that he does not want to share. He might feel that even though you are good friends, you are not compatible as a married couple. It is also possible that he is not ready to exclusively date or marry anyone, a feeling about which he may, or may not, even be aware.

Instead of feeling insulted or rejected, you can view your relationship with Zack as a positive learning experience. Your relationship can serve as a stepping stone to a future long-term relationship with a man who adores you and wants to marry you. Your friendship with Zack demonstrates that you have strong interpersonal skills. It also highlights several other desirable qualities that can draw the right man toward you. You have an endearing personality, you are a giver and you are a great friend. Keep your wonderful qualities in mind as you date other people.

At the same time, your relationship with Zack might have helped you notice some qualities about yourself that are not so ideal. That can help you avoid potential issues in a future relationship. Maybe Zack has given you some feedback that can help you improve yourself. You also might have noticed some thought or behavior patterns you have had in your relationship with Zack that could get in the way of forming a stable, healthy, long-term relationship with a man in the future.

If you explore these questions, you can use your relationship with Zack as an opportunity to discover areas for your own self-improvement and personal growth so that you are prepared to be your best self and you can identify the right man for you when he comes along.

As you pivot away from hoping that Zack will come around and look in another direction for a potential life partner, it is important that you open yourself up to dating those people with a full heart and a clear mind. Be ready to move full speed ahead with a man who has the qualities you are looking for and who wants to date you. Avoid comparing this new person to Zack. Even though you have had a nice friendship with Zack, there is something critical he is missing: he is not running to marry you. By comparing a new man to Zack, you will effectively be holding on to a fantasy image of Zack being the perfect guy and this will distract you from truly appreciating a man who is really right for you.

It may take time for you to meet a man who you appreciate and who appreciates you even more than you can imagine right now. In the meantime, keep yourself from getting emotionally burned out and disappointed by passing over men who are not interested in you. The more you can let go of your focus on Zack, the more you can move ahead finding a man with whom you can build a trusting, loving and satisfying relationship.

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 online course: The RELATE Technique™—Seven Steps to Emotionally Connect Through Conversation. Maybruch can be reached at [email protected].