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The Finish Line

By Henni Halberstam

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July 2, 2026, 1 PM ET

Dear Dating Coach,

I met a great girl on a Jewish dating website, and we have been taking things slow. Recently, she has been pressuring me to see where I “think this is going.” I told her that I really don’t want to rush. We are having fun, so I don’t get why she can’t just relax and see how things develop. I feel like everyone is always so focused on a timeline that they don’t get to really enjoy dating. I like her, and I like dating her. Shouldn’t that be enough?

Super Chill

Dear Chill,

There is a guy I know (OK! I made him up!) He signs up for flying lessons. Every Tuesday, he’s at the airport wearing aviator glasses, a bomber jacket, carrying a flight bag, and learning about take-offs and landings. He masters weather patterns, emergency landings, and airplane jargon. A few months pass, and his flight instructor tells him he is ready for his first flight. The guy shrugs and says, “Oh, I just like planes, I don’t actually want to fly anywhere.”

This is you.

I hear where you are coming from. You found someone you like. Dating her has been great. You like spending time with her, and you are both enjoying your dates. Why rock the boat? (Err… plane!) You are feeling the pressure, and you don’t like it. But she is focused on the future and needs answers.

I Put My Phone in Airplane Mode. But It’s Not Flying

We don’t date just to date. We date for marriage. We date so that we can learn if we are compatible and if we will be able to create a happy and successful marriage. Dating endlessly after you have answered all your questions about said compatibility is a lesson in futility. If you are sure that your personalities complement each other, that you share the same goals, that you have chemistry, that you live with the same hashkafa, and that you feel safe and happy, then you are likely ready to get engaged. If there are any concerns that you have, address them. If you are anxious about anything, discuss it. But if you are in a place where you feel sure about her as a partner, but are just happy to keep dating, then you are wasting her time and yours. Endlessly dating only introduces concerns that don’t matter. It allows the mind to focus on trivial issues that invite cracks to form in a relationship that does not yet have a full commitment. Dating is not about the journey; it’s about taking flight. That’s the goal. It’s time to board the plane or let her go.

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