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Thoughts from an Older Single

Reset your mindset and mentality around the dating process - dare we say, treat it like a job interview.



As an older single, the dating process can sometimes feel disappointing or tiring, but I’ve found that having the right mindset and approach is very beneficial. Forgive the analogy, but think of it like you do the job search process. Of course the decision on a job is both emotional and logical. Ideally, you need to have a connection with the folks there, connect to the type of work it is and the clients you’re serving, etc. Additionally, it needs to make financial sense, and a commute of 2 hours won’t be viable, also it should help you gain new skills or strengthen existing ones, and so on. Obviously, there are a lot of factors. So giving yourself a structure and framework to approach the process can provide a healthy path forward. Below are a few tips that can help you develop this framework. Some folks may disagree with some of the below, and of course each person is so different it’s hard to provide generalizations, but I feel confident about them given what I’ve learned thus far.


1. First and foremost, it is so important to know yourself. When people told me that, though, it felt extremely daunting and confusing. “What do you mean ‘know yourself’? Of course I know myself. I’m me! Or don’t I? So, is there something else I have to learn? Is there a place I can go to do that? Is there a specialist on this I should speak to? Does this require deep meditation? Where’s the nearest forest?” were just some of the early questions that stirred me. I want to say a few things about this:


a. Yes, you do know yourself already to a certain extent. Trust that.


i. Spend some time thinking about your life experiences. For example, what types of compliments and constructive feedback have you gotten in your life? Think across various spheres of your life (personal, professional, amongst friends). What are you naturally good at? What’s comes a bit harder for you? What environments do you thrive in and why? What sorts of people are you naturally attracted to and what do they have in common? Who are some people you respect, why, and what do they all have in common? Which middot (character traits) most characterize you and are you on more of an extreme end of a spectrum for some? Which yes and which are you a bit more in the moderate area on?


ii. Regarding that last question, I’ll give a personal example to help clarify. I am type A. I am organized, planned, and detail-oriented. Socially, I’m a

chiller. But in many capacities in my life I am very type A. If type A is the

right of the spectrum and type B is the left, and I know for myself that I’m pretty much at the far right (in this trait). Therefore, I likely won’t do well with someone all the way to the left. I am not saying it’s impossible, of course anything is and we’ve seen all sorts of “unexpected” yet BH happy marriages, but if this is a key trait in you and you are far to one end, likely you need someone not totally to the other end. This is a framework.


b. Also though, we will BezH be continuing to learn about ourselves for the rest of our lives so the question is more the extent to which you need to know yourself. Some people pretty much know to the extent they need, and for others it is actually the dating process itself that brings them to enough self-knowledge. If that is the case, enjoy the dating process and trust it! Grow from it. If a relationship ends, spend time journaling and thinking through what went down. Learn from it. Much of the personal work I’m doing now came from insights I drew about myself from dating.


2. Understand that dating may be quick or it may take time. If it’s quick, lovely! If not, that’s great too. We each have our unique nisyonot and only Hashem sees the larger picture. Hashem has a plan for each of us and dating is one of the greatest fields for working our emunah and bitachon muscles. One of my Ravs says that emunah and bitachon are not “you either have it or you don’t.” Mamash not. Like all other middot, every day we must work to build and strengthen them.


3. Comparing yourself to others is likely the greatest waste of time you can indulge in. I could speak about this for hours, but please just take my word for it.


4. Head and heart. We need both, and decisions should be made with both. I believe Rav Dessler says the greatest distance is between the two, so that should give you comfort if/when they seem to be relaying differing messages to you. The point is, acknowledge both. Be mindful. Moreover, if you’ll only be dating a short time before getting engaged,

the “head” should play a more critical role. Of course, you need to feel a connection, enjoy being with the person, etc. But the match, to a certain extent, should make logical sense too.

5. Practice your listening skills. Practice with your friends or family. When speaking to someone, try listening without interjecting your own thought or opinion for longer than typical for you. Practice this a lot; work that muscle. I am not saying not to share on dates; of course, the dialogue and dynamic is key and you should share your thoughts, opinions, and ideas. But, it is very important to be fully present in dating, which will also lend itself to the final tip:


6. I highly recommend spending time after each date - digesting it. If you excelled in the above exercise on the date itself, this “processing” part will likely be easier. You may be working with a shadchan who wants to hear from you right after the date (I am a major supporter of working with a shadchan and do so myself), but digest first. This may mean sleeping on it and speaking with the shadchan the next day. Some ways to digest: journal, talk out loud with yourself, think alone with yourself, or soundboard with a mentor. For the latter though, always first spend time alone. This will ultimately and cumulatively help with the first point - knowing yourself.


So, having the right approach and mindset in dating includes knowing yourself enough, knowing what to expect (i.e. it might take time - in general to find the match and to learn about yourself), learning and growing from every interaction and relationship, being mindful and present (with yourself and the person), acknowledging both the head and the heart and keeping both in check, and spending time with yourself.


I hope this or at least some of it resonates, and BezH all those looking for their besheret will find him or her soon!


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