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A Dating Guide: 3 Ways to Transform Your Dating Experience

There are probably thousands of articles written about the dating experience in both the shidduch and non-shidduch worlds. Though there are many variances between them, one thing is certainly universal – dating is hard. It’s hard to have patience, weather rejection, not get discouraged when the process becomes longer than anticipated.

Dating: A Tool


The most empowering action we can take is to use dating as a tool for self-development. We can grow from every positive and negative dating experience we have. Each encounter offers a rich understanding of ourselves and the areas in which we can improve.

Relationships are like mirrors that give us a chance to see ourselves through somebody else’s eyes. Everything that happens on a date is teeming with information about how we are perceived as a potential husband or wife. The feedback we get from a potential life partner – from what they say and don’t say, to the way they treat and look at us – offers a wealth of information we can use on the road to getting married.

Here are three tools that can ease the dating process and transform it into a rewarding life stage and growth opportunity.

1 Know Your Why

In his famous Ted Talk “How Great Leaders Inspire Action”, Simon Sinek shares his groundbreaking theory: Start with the why. His theory pinpoints why some businesses succeed while others fail. Companies who truly know their why know what they want to accomplish as a business. Sinek discovered that these businesses garnered a stronger and more loyal customer base than ones with better or fancier products. He explains that people don’t buy what you do; they buy why you do it.


This concept can also apply to the dating world, and to any time we are embarking on a new chapter in our lives. The why represents the reasons we want to do something, it symbolizes the motives and drives behind our actions. It is so important to know the why before we set out to accomplish something. When it comes to dating, starting with the why means digging deeper and asking yourself why you want to get married to begin with.

This may seem like a funny question to ask. However, answering it can help give you the clarity you will need to make the right decisions in tough circumstances, prevent you from compromising on our true goals and values, and help you deal with the inevitable rejection that comes with the dating process.

It’s important to note that it is possible for your why to change throughout the dating process. When you decide to start dating, you may think you know what you want. It is perfectly normal to discover that you want different things; it means you are learning from your experiences.

2 Set Your Efforts, Not Your Goals

Once you understand why you want to get married, you can start working towards that goal.
This is a good time to remind yourself about what is and what is not within your control.
Demoralized singles frequently share with me how powerless they feel. This feeling of disappointment is completely understandable. It stems from our natural tendency to look at our goals in terms of results rather than efforts. However, there are more effective ways to structure our goals.


Take, for example, the goal of boosting energy levels. This is a goal stated in terms of the results you would like to see. Compare that with the goal of sleeping eight hours a night, and drinking ten cups of water a day. Doesn’t the second version sound much more attainable? That’s because it is. Almost all goals we set for ourselves, including getting married, feeling high energy, and receiving a promotion at work, involve many factors that are outside our locus of control. We don’t have the power to put the right dating prospects in our zip code, change our genetics, or make our professional competitors disappear. So, then what can we do? We can focus on our efforts.

The results-oriented voice inside our heads says, “I need to be married by June next year.” We can replace it with “I want to meet 50 new people this year, whether they are potential dates, shadchanim, guests at a Shabbos meal, or people at events.”

We can set goals of reading three books or seforim on self-improvement, daven or meditate, or develop new hobbies. We can put forth physical, emotional, social, and spiritual efforts, whether through prayer, therapy, networking, fitness, or socializing. When done consistently over time, these will undoubtedly bring us the closest we can possibly get to our marriage goals. At the very least, our efforts will yield tremendous personal growth and satisfaction.

3 Mindfulness

There is so much to consider, and so much on the line, as well as many additional pressures that surround our dating lives. It’s therefore no surprise that we might spend our dates contending with an endless stream of internal questions and concerns.

However, whenever we think too deeply about an experience as we are experiencing it, we run the risk of detracting from the experience itself. This is true even with positive experiences. Imagine treating yourself to a scoop of your favorite ice cream after a hard day at work. As you taste the sweetness of your dessert, your mind starts thinking “I hope this ice cream takes the edge off the day I had and makes me feel pampered!”

It may sound silly, but our internal dialogue on dates can become just as distracting. The best thing that we can do in those moments is to stay in the moment and not allow our thoughts to pull us away.


There are many short exercises you can try to ground you in your present reality. One such exercise is to push off the distracting thoughts by telling yourself that you’ll get to those thoughts later. If you tell yourself that you cannot think about those thoughts at all, you’re mind will bring you back to them. Telling yourself “not now but later” addresses the mind’s concern to make sure you’ll give attention to those thoughts at some point.

The next step is to reorient yourself to what is being said in the conversation with your date. Like adjusting the lens on a camera, our minds can only focus on one dimension at a time, so staying grounded and keeping yourself attentive to your conversation partner’s joke or story prevents you from wandering off into thoughts about it. By engaging in conversation and asking concrete questions, you take the focus off yourself and your internal experience and can be more grounded in your dating experience.


It’s hard to learn much from our dating process, or even enjoy it for that matter, if we aren’t fully present for any of it. This is even true of the dates that we don’t think are right for us.

Meant to Be


We say every day hameichin mitzadei gaver, G-d gives us the experiences we need for our personal growth. Every person we meet in our lives, every experience we have, is just as meant to be as the person we marry. We can relax and simply enjoy a conversation with another human being for a couple of hours rather than putting undue pressure on ourselves and the other person. Even if the date is quirky or different or “so not for us,” there is something to learn from our time with everyone. This mentality doesn’t just make dating more enjoyable, it also relieves some loneliness as it helps us appreciate and feel more connected to others.

Interested in more? Try these:

10 Ways to Kick Rejection to the Curb
Mindfulness: A Practice in Living in the Now
Lost Piece of Heart
What to do when it’s not for you

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This Post Has 6 Comments

  1. “However, whenever we think too deeply about an experience as we are experiencing it, we run the risk of detracting from the experience itself” This is a great point. Far too often I feel myself thinking about the significance or fall out of a moment instead of actually living it to the fullest.

    1. Yes, exactly, it’s a fairly common experience which can be a result of so many things including our use of technology, which decreases our attention spans. I had a mentor in Israel who would run tours of the country and would encourage his tourists to put down their cameras and take in the views before taking any pictures. That message always stuck with me – take mental snapshots, be in the moment, look where we are, and actually LIVE the memory before trying to document and remember the memory.

  2. This topic is very interesting. Is it possible to ask a jewish woman out if your an outsider? Like how does that work? Asking is not the problem for me it’s the respect that I feel because of laws, being orthodoxy etc. Let me know what my chances are if I even have one period.

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