Broker Check

Practical Planning Tip: How Much Should You Spend on a Date? – Part 2

April 16, 2026

Today, I’d like to CONCLUDE our video series on the topic of “How Much Should You Spend on a Date?

Today, let’s start by discussing, the Focus on ROI (or Return on Investment): Going to a fancy steak restaurant, may be a bit extreme for a first date. Dropping $300 on someone you may not want to see again may be financially imprudent and is certainly not necessary. However, there are certain points in one’s life where making a big investment may make sense. A down payment on the right house or buying into a business may be sensible financial decisions that pay off meaningfully in the long run.

In the dating world, if you’ve been going steady for a while, and you both really like one another, then it may be time to graduate from bowling to Barnea or from going on walks to Wall Street Grill. The logic is simple: Invest several hundred dollars, take your relationship to the next level, and then build a bayis ne’eman together adme’ah v’esrim shana. That high restaurant bill may be the best ROI anyone can ask for.

Finally, let’s discuss the role of hashgacha pratis: It seems silly to discuss dating and money without any mention of the hand of Hashem in this process. As I already mentioned, my typical first date was coffee. However, when I went out for the first time with my wife, I happened to be famished (as was she) after a long day of work. I decided to take her out to dinner at Mr. Broadway. I found out later that Lauren doesn’t drink coffee. Had I gone my typical route, we would have been two hungry people meeting at a coffee shop, not drinking coffee. Under suboptimal circumstances for building a connection, there may not have been a second date. Hashem guided me to make a decision that went against my normal dating philosophy. Despite my background in shadchanas.

This story is the definition of “hashgacha pratis,” which is the belief that Hashem is actively involved in the details of all creation and serves as a guiding force in every individual’s life. This concept suggests that nothing happens by mere chance. Even the smallest events are guided by a Divine purpose.

When it comes to dating, investing, and life in general, it’s important to put in effort. In the dating world, this means dressing like a mensch, behaving respectfully, and doing research to find an enjoyable venue to get to know the individual you are courting. Yet, we must also appreciate that ultimately success in any endeavor is up to Hashem. No amount of money spent at a high-end restaurant will change this ultimate truth.

You can WATCH the full video here.