June 26, 2026 Categories: Features / Marriage and Relationships
Count Your Blessings
(The Jewish Press)
Dear Dating Coach,
I am dating someone wonderful. I really like him, and we both feel like we are heading toward an engagement. Everything has been pretty smooth, and we have been progressing since day one. But now my sister is in my ear, questioning me. She can't believe how well things have gone, and she is worried that this was “too easy.” So now I am in my head, worrying that I am missing something and might be making a mistake. Am I being foolish, or am I missing a huge red flag? I don’t want to mess this up. Please tell me if I have blinders on.
Super Focus
Dear Super, When I was younger, I used to love to give my Barbies haircuts. I would trim a bit here and there, and then step back to check on my handiwork. “Too simple,” I would say. “She still looks like herself.” And I would cut just a bit more. Then I would brush that blonde bob and determine that she lacked an artistic flair. So, I would trim juuuust a little bit more. Soon enough, poor Barbie had barely a wisp to her mane. Shorn and uneven, Barbie hung her head in shame and refused to leave the Barbie box. So, I would reach in for her sister, and “beauty shop” would commence. “Don’t worry,” I would reassure New Barbie, “Just a trim…”Count Your Chickens, and Gather the Eggs
Thank you for your letter. You met someone, and you have been slowly building a connection based on your mutual goals, personalities, and chemistry. Everything has been going well. Every date feels like a step toward closeness, and your time together has been enjoyable and smooth. Now your sister believes that dating can't be this easy. It needs some drama! She is worried that without conflict, there can't be a resolution! You need some sort of plot twist to get toward a happy ending! So now, you are concerned that you have missed a red flag along the way that could potentially ruin everything. Breathe. You are not missing anything. Everything has been going smoothly because it can. You don’t need conflict or disagreement. You don’t need an issue to address or a problem to fix. Dating can be simple. You have been blessed and herein lies the actual challenge. We are afraid when things are too easy. We often won’t allow ourselves to relax into joy because we are worried that “the other shoe is about to drop.” So, we look for setbacks where there are none. We create questions that we don’t have, and we manufacture concerns to diminish our simcha. Don’t allow this to happen to you. This is a beracha. Accept it, embrace it, and allow yourself to enjoy it. We are so happy for you.
