Dear Dr. Chani,

Over the three years that I have been dating, I have dated many guys. There is one person who I dated right at the beginning who I thought was not for me, but now that several years have gone by I am rethinking my decision. I am wondering if you think I should ask someone to set us up again.

When I first got back from seminary, someone set me up with a guy who lived in my neighborhood. We went out on a few dates, but in the end I decided that he did not fit the image of what I was looking for. Looking back, I remember that he had refined character traits and a relaxed personality but he did not come from my kind of family. Most people would consider my family to be very well off, and I was looking for someone that would fit into that same category.

My older brothers all have custom-made suits, are well versed in all the fashionable brand names, and take pride in how they look. However, the guy that I was dating looked very old- fashioned in my eyes; he had strange looking glasses, a cheap suit and a weird haircut. I vividly remember trying to focus on the conversation and all of his positive qualities, but most of the time I kept thinking about how he looked. Since it was my first guy, I thought that I had nothing to lose by breaking it off because I would probably find someone better down the road.

Sadly, that was not the case. It’s been several years since that first relationship and I have dated many guys. From time to time, I have thought about if it was immature of me to have passed up such a good shidduch. Was I foolish to have broken it off with him because of his appearance? I wondered to myself if maybe I am too superficial and I should have compromised.

It all changed last week. My good friend was getting married. I arrived at the hall and was shocked to see the first guy I dated getting a drink from the smorgasbord table. I am used to seeing guys that I’ve previously dated at weddings and acting normal toward them, which is why I was surprised when I started to feel like I missed him. He said hello and smiled at me. During the dancing, I inquired about him to find out if he is married yet. I heard that he is still dating.

When I got home, I could not get him out of my mind. I am thinking of asking someone to set up the shidduch. I feel like I am ready to give him another shot, this time appreciating his good qualities, yet I do not know if I should risk breaking his heart again. What do you think?

Sincerely,
Miriam

Dear Miriam,

You have come a long way since your first experience with dating. Through the process of dating, you have gained clarity about what is important to you. You have a heightened appreciation of how precious it is to find someone with impeccable middot. This is why you are strongly considering going out again with the first guy you dated. At the same time, you are self-aware enough to know that you still care about image and the way the guy presents himself may still bother you enough to break up with him again.

One of the points to consider as you explore whether or not to give the relationship a second chance is what might be influencing your emphasis on image. Ask yourself: “How much of my concern with his image is coming from my own values and how much am I worrying about what ‘they’ will think or say if I choose to marry him?”

“They” may include your parents, friends, teachers, coworkers, or even previous people you dated. It is common for people who are dating to combine their own intrinsic values with the expectations of other people. The influence of what “they” will say can make you care about or put extra emphasis on certain aspects of a person that would otherwise not necessarily be so important to you. So it is wise to distinguish between aspects of a person that are important to you personally and aspects that you care about because of what “they” will say.

Keep in mind that, to a certain extent, it makes sense for you to care about what “they” will say. Ideally, you want people who matter to you to rejoice with you when you choose who to marry, so it helps for them to agree with your decision. In addition, people who know and love you can have your best interests at heart when they have higher standards for you than you do for yourself. “They” may be able to recognize aspects of the person you are dating that you are not concerned about because of blind spots that are preventing you from noticing them. Therefore, you should not necessarily entirely disregard the influence of what “they” will say.

Yet differentiating between what truly matters to you and what you care about because of other people’s expectations can help you gain perspective and help alleviate some of your concerns.

What if you determine that you personally care about his image? Then it is important to rank what you care about in order of importance. Generally, it makes sense to rank personal qualities that will affect your relationship and the quality of your marriage above qualities that are extrinsic to him and do not need to affect your day-to-day interactions with him. It sounds like you have already prioritized his sterling middot above his sense of style since you are inclined to go out with him again. This makes sense since middot are the most critical factor in how your relationship will develop.

What can you do to help resolve your concerns about his image? After you give it time for your relationship to re-develop, bring up topics that have to do with fashion, brands or clothing and ask what he thinks about them. See if he has strong opinions about how he dresses or if he simply does not put much thought into it. If he does not really care much about what he wears, ask him what he would think about you taking him shopping for a new wardrobe and an updated haircut. Although you might be afraid to insult him, he might actually not object. You would be surprised at how many men are delighted to have a woman shop for them. Having this conversation openly can give you a practical way to adjust his style and alleviate your concerns.

As you consider re-dating your first guy and you are sensitively concerned about “breaking his heart” again, keep in mind that you are both in the same boat. You are both still dating. Reaching out to date him again is giving you both a second chance to create a great relationship. This potential is usually worth the risk of having to go through a breakup a second time. Taking into account your personal growth and the new perspective you gained through years of dating as well as a plan to communicate openly about your interest in helping him adjust his image, you may be well on your way to developing the relationship of your dreams.

Wishing you much success,

Chani

To all my dear readers — Wishing you a sweet New Year filled with joy, blessings, contentment and peace! May we merit to see a complete redemption! New — Premarital Education Workshop. Take my fun and interactive three-part series on effective communication, conflict management and more. Build a strong foundation for your marriage!

Dr. Chani Maybruch is a social psychologist who has specialized in helping people build and enhance their relationships for over two decades. If you would like to improve your relationship with yourself, your loved ones or others in your life, reach out to her at chanimaybruch.com.