Photo Credit: Jewish Press

Dear Dating Coach,

I am dating someone and we are close to an engagement. He is wonderful and everything I could have hoped for in a future husband. I only have one tiny qualm; he is the first guy I ever dated. Everyone keeps telling me how lucky I am, but I worry that having never dated anyone else, I may be missing something. I want to get engaged, but these thoughts are really bothering me. How do I lay these fears to rest?


Dating Done


Dear Done,

I remember reading about this couple in Seattle who won a 90-million-dollar Powerball jackpot. They both had never played the lottery ever before. One Thanksgiving they decided to buy a lottery ticket on a whim and stuck it on the fridge with a magnet to remind themselves to check their numbers. When they realized that they won the Powerball they threw the ticket straight into the garbage. Nope. That’s not true. They turned in that ticket and lived happily ever after.


Mega Millions

Congratulations on this special time. You are getting ready to plan a future with someone that seems perfect for you. Yet, as you contemplate an engagement, you can’t seem to erase a niggling voice that tells you that this blessing has come too soon. You wonder about sayings like count the fish in the sea and think that perhaps you pulled your line too quickly. Maybe there is someone better out there for you that you won’t know about if you agree to spend the rest of your life with the first incredible guy that you have dated. Maybe there is someone smarter, kinder, taller, funnier, who you will never have the chance to date.



You have been blessed. Hashem has offered you your zivug on the first try and the parts of ourselves that fight the brachos in our lives are trying to offer you doubt when there should only be joy. A gift has been given to you, and a part of you feels like it should reject the happiness so readily offered. Perhaps now is the time for self-reflection. A chance to consider why you feel the need to diminish moments of joy and celebration. Perhaps, a self-evaluation to consider giving yourself the permission to receive good without self-doubt or a need to downplay the “happy” in some way.



You won the Powerball. A treasure, a blessing, a miracle offered to you so seamlessly. Show your thanks by being gracious and grateful. Be generous with your family and the friends who have not yet been given this bracha. Think about offering goodness back into the world in appreciation, but don’t throw away this gift. It’s a once-in-a-lifetime opportunity. Say thank you, and live happily ever after.


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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 to schedule a phone session.