Photo Credit: Jewish Press

Dear Dating Coach,

I have been dating for a bit and feel like I have lost my way. I have dated some people that I liked and some, well, I didn’t like. The most difficult part of dating for me is not knowing “everything” about the person you are dating. I know that this is impossible, but the “unknown” really worries me. What if they seem great, but I have missed some terrible character trait or part of their history that will affect our future? Is there anything specific I should be mindful of when dating? Please help.


Maybe Flagged


Dear Flagged,

Teenage drivers are scary. This is basically a fact. I’m sure you agree. They believe that they are all immediately qualified for Daytona, love night driving, and are committed to the power of loud music to provide driving directions. Yup, scary. Thankfully, they must pass a permit test and later a driving test before they can get their licenses, so we can feel more assured when they finally make it to the road. Kind of. The permit requires them to memorize road signs so that they can adhere to whatever future map they encounter. Those road signs are hard. I have been driving for (many, no need to get technical here) years and I didn’t recognize some of those signs. Who knows when I might need a “gravel warning sign?” You can never be too prepared.

Dating can be complicated and sometimes direction really helps us to get back on course. It is true that it can make us feel anxious when we acknowledge that there will always be some element of the unknown even when we commit to marriage. We can however, be reminded of certain “red flags” to look for before and while we date someone new. So, pause and refocus on the three R’s, reputation, reaction, and real-time.



Take the time to research the person you will be dating (or have your parent do this for you). Listen to how the people in their lives describe them and see if they have a nice reputation. Are they well-liked, respected, and do others think kindly of them? A reputation is something that someone builds over time, so we can trust that this is going to give us a better understanding of their true character and behavior.



It is very important to have a healthy and objective listening ear when you date. This may be a parent, a dating coach, or even a smart friend. Share the parts of your dates that gave you pause, and seek their advice. Their objective opinion will help you to clarify any concerns you might have and allow you to discuss any parts of your dates that made you feel unsteady. Having someone to talk things through with can really help before you chose to go out with someone and while dating.



Trust your dating process and what you can see with your own eyes. Look at the way your date behaves on your dates. See if they are kind to the server, the valet, and of course to you. Listen to the stories they share, and the way that they respond to yours. Believe in your own judgment and intuition. If your date seems like a mentch, they are likely a mentch. So, take a deep breath and let the three R’s be your road signs to a clear and happy future.

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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.