Photo Credit: Jewish Press

Dear Dating Coach,

I dated someone for a while and he recently called things off. I was really upset but understood that I couldn’t control his feelings. Over the next few days, I shared what happened with my family and some close friends. To my surprise, they all looked relieved, expressing some variation of, “I never liked that guy!” Now, I am second-guessing all my choices. How can I trust my own judgment when negative qualities that were so clear to others were lost on me?


Self Doubt


Dear Doubt,

Florida has a special weather phenomenon that terrifies its drivers. The skies can shine blue with nary a cloud as drivers race toward their destinations. Then completely without warning, a heavy downpour will drench the cars, making it almost impossible to see the road ahead. The drivers will clench their steering wheels with white knuckles as they put their windshield wipers to the test. The limited sightlines will overwhelm and then without warning, the highway will be completely dry. As if there was an invisible line in the roadway between rain and shine. Drivers will shake their heads, baffled, as they second-guess the storm that just passed.

Thank you for reaching out. I am sorry to hear that you recently went through an upsetting time. You were ready to accept that while you were interested in moving forward with someone you connected with, he did not feel the same way. You reached out to those close to you for support and care, and were shocked to hear that they never appreciated the person that you felt so invested in. Now, you wonder about all of your dating choices and your ability to discern between good and questionable behavior.

There are some ideas to remember before and during meeting someone new to help you ensure good dating decision making.

Research: Doing research before a date will offer a more comprehensive view of a person suggested to you. Taking the time to reach out to those who know a potential date will offer insight into personality and character traits before you even meet them. Gauging the impression that this person makes on others will paint a picture that can help you to make an informed decision before becoming emotionally invested.

Guidance: Take the time to pinpoint those in your life who will be able to offer you guidance if needed. This can be your parents, a rabbi or rebbetzin, dating coach, or even a wise friend. This way, should you feel conflicted at any point during the dating process, you have a “team” ready to listen and offer advice if asked. They can likely call your attention to potential red flags that you may have missed.

Balance: When you are dating someone, do your best to take note of the balance in the relationship. Take the time to assess the time, care, and energy that both parties offer as things progress. If one person is constantly giving more of themselves than the other, than the lack of balance may be an indication that something is not right.

Your willingness to do research, to seek guidance, and to mark the relationship balance will counter self-doubt and allow you to move forward with the confidence that you are seeing the road ahead clearly.


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Henni Halberstam is a Dating and Marriage Coach whose expert advice will help you navigate dating and relationships in order to ensure a successful marriage. You can contact her at [email protected] to schedule a phone session.