Most single people I know in their mid to late twenties (and definitely older) don’t particularly enjoy dating. They don’t look forward to a first date as much as they did in their late teens and early twenties. I know of many people who are willing to remain in unsatisfactory relationships just to prevent themselves re entering the dreaded dating scene. As a rabbi working with young singles in NYC over the past 15 years I receive daily emails, text messages and phone calls from people complaining about the challenges and uncertainty that comes with dating. An example of comments I repeatedly hear include: “There aren’t any good guys out there!”.  “Girls are not interested in a guy without money”. “Why can’t he/she commit?” “She keeps pressuring me to get married and I’m not ready”. These and other such frustrations have become the norm in the course of most people’s dating experiences.

After advising and setting up many singles, and performing well over a hundred weddings I wrote a book with advice on dating, relationships, love and marriage, called “Will Jew Marry Me?” click on the link to preorder a copy.

I’m not claiming by any means that I can fix all your dating woes, but I’d like to suggest a few rules which will improve your dating life, and lessen the anguish that has now become the norm in dating.

Rule One: You must call within twenty four hours of the date

If you can’t call, then at least reach out to thank the other person for the date and then follow up within twenty four hours to either set another date or have “this was great but not right for me” conversation. Leaving people hanging is disrespectful and in most cases downright annoying. People have lives to live and don’t have time to waste attempting to guess whether you are interested or not. Dating is hard enough without adding a whole lot of additional guess work. 

Rule Two: If a relationship doesn’t work, don’t be bitter, find someone else for them to date

I understand that this may sound insane. Who in their right mind would set up their friend or even an acquaintance with someone who you just broke up with, or worse, who broke up with you? The answer is that just because he/she wasn’t right for you, doesn’t mean they aren’t right for someone else. This applies even if the relationship didn’t end so well, which chances are it didn’t. Setting up an ex is challenging, I realize that, however by doing so two things may well happen a) you’ll get over your ex faster b) people will see you as a selfless person, and be willing to set you up too. What goes around comes around. 

Rule Three: You need a middleman/woman to act as an advisor and go between

Dating has become insane, you can’t do it alone. Your dating life is probably filled with much uncertainty and so many mixed signals that you need to know morse code to decipher where you stand in the relationship! This lack of clarity can be alleviated with a person who knows both of you to act as a middleman/woman. You can ask someone you both respect to be that person. You could use a rabbi, therapist, married friend or hairdresser. A tactful, smart friend who has success in their own relationships you both agree on, can be a sounding board in a relationship, especially early on when you are getting to know each other and later in the relationship when you are figuring out whether you have a chance of marriage. 

Rule Four: Don’t take him/her as a “plus one” to a friends wedding unless you are really serious about the relationship

I’ve had many people tell me after a relationship break up that they were totally shocked and never saw it coming. When I ask them why they respond “well he took me as a plus one to his closest friends wedding.” Just because you were invited as their guest, doesn’t mean they are interested in building a relationship. It does mean they like you and are glad to be seen with you at a nice affair. But that may be it. 

Rule Five: Date one person at a time

I’m going to make this rule its own topic for a future blog, but wanted to add it here anyway.

Happy Dating!