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Four Questions to Dating Freedom

Four Questions to Dating Freedom

Passover teaches us the deeper meaning in the search for a soul mate.


"In each journey of your life you must be where you are. You may only be passing through on your way to somewhere else seemingly more important – nevertheless, there is purpose in where you are right now." (Rabbi Tzvi Freeman)

On Passover night, we speak about the birth of the Jewish people through the "Four Questions" in the Haggadah. In asking how the Seder night differs from other nights, we are guided to the important themes of our liberation from Egypt. As my own status as a "single" has continued for more years than I care to admit, I realize there has to be more meaning in the search for a soul mate than finding a partner for life.

As important as this goal is, I also search for purpose in the process itself. The alternative could be a growing enslavement to negativity, self-doubt and hopelessness. So in the spirit of Passover, I offer other singles a list of "Four Questions to Dating Freedom." Such questions are not meant to deny the natural feelings of hurt and frustration that accompany the dating process. However, they can help one see a deeper purpose in this stage of life.

1) What Can I Give?

When one thinks of doing kindness for another, images of helping to run a food drive, visiting the sick or doing a favor for a friend come to mind. Though such acts require an investment of time/money and other resources, we usually feel good afterward because of the deep satisfaction of helping another person and actualizing an important value in our life.

In general, we do not view going out on a date to be an act of kindness. To some degree it becomes like any other task with a goal, in this case to develop a relationship and to have a nice time while doing so.

While that is obviously important, a date can also serve as a chance to offer respect and care for another person. The form this takes could vary from person to person. In some cases, the act of treating someone to a nice meal in a restaurant, and truly listening, can lift the other person’s spirits and make her feel better after a stressful week. Or, as the date describes a problem she is dealing with at work or home, I can share a lesson I heard at a seminar that could help find a solution. On a deeper level, if she is receptive, I can discuss spiritual ideas that could increase her (and my) trust in God in a way that transcends the outcome of the relationship.

2) What Can I Learn?

To some degree, this is the flip side to the first question, although they are certainly not mutually exclusive. Ironically, in the midst of other responsibilities, it is possible that my longest face-to-face conversation in any given week may be with a woman I've never met and may never see again. So besides the more obvious purpose of a date, I try to recognize that the woman I am with may be a messenger to teach me something about myself that I need to know.

For example, I recall one conversation where a date told me about a group she was part of which practiced a special technique for getting closer to God. This discussion led to some insights that still resonate with me today. Another date shared her feelings about the situation in Israel with such passion that it made me wonder if I was really doing enough to respond to the crisis there. There have been women who informally offered career advice (probably not a good sign on a date) or allowed me to see other issues in a new light.

3) Why Am I Here?

Of course, the purpose of dating is to get to know someone better. But perhaps that's only on the surface. On more than one occasion at a restaurant, I complimented the owner on the food and wished him luck. Maybe he needed to hear that to combat some of his anxiety about whether his venture would be a success. Another time I met a woman at the Port Authority of NY (admittedly not the most romantic place) and we ran into a friend of mine who was having trouble finding her young daughter at the terminal. My date and I both joined in to help to locate her.

The bottom line is that on almost any date, other people and situations will surround us. Perhaps we have been paired up with our date to make a difference in the lives of others in a way that neither of us could have anticipated.

4) How Can I Grow?

Every day I pray to God with a multitude of requests: health for those who are ill, jobs for those who are unemployed, and my own daily needs. If I have so much as a bad toothache, I can ratchet up my prayer intensity quite quickly! But on an ongoing basis, I would be hard-pressed to find any other issue I prayed about as much as "finding the right one." In doing so, I’ve been forced ask myself what I really want out of life and the values that are most important to me. I’ve developed the trust in God that as long as I put in reasonable efforts (as opposed to being on 23 websites and going to events to meet people every night), God is ultimately in control of how and when I meet my soul mate.

On an interpersonal level, I'm constantly being tested to see if I can "walk the walk" of being the person I want to be. When a Jewish couple gets married, friends will offer an excited "Mazel Tov!" But until that time, most of us may have to settle for an "inner mazel tov" when we pass tests that no one else may be aware of:

  • Can I resist the temptation to tell my friends about how poorly (from my perspective) I was treated by a woman and point out all her faults, when doing so serves no constructive purpose?
  • Can I avoid being abrupt or rude with the woman I'm talking to at a singles event, so I can race across the room to speak to a woman who does interest me?
  • Can I be fully present and treat a woman with attentiveness and respect when after five minutes (or less) I don't think there will not be another date?
  • Can I have the integrity to not pursue a relationship which could be comfortable, but inconsistent with my values?

As the Seder moves on, the "Four Questions" bring us to the point where the Jewish people, freed from Egypt, develop a true relationship with God a few weeks later at Mount Sinai. It is my fervent hope and prayer that this Seder night, those searching for a partner in life can respond to the questions above in a meaningful way. In doing so, we can gain the freedom to better connect with God others and ourselves.

April 9, 2011

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Visitor Comments: 19

(18) Good Advice, October 11, 2015 1:06 AM


My concern is that it is human nature to want validation. While questions such as those listed above may guide those that are without a clue, I would urge everyone to actively listen to what their partner says.

Too often, people use suggestions such as these to trump (or filter) what they hear. As a result they often are further away from freedom than ever.

If you think there is a subtext-ask the person. Do not assume.

Trust that they know what they want.

If they don't say something you wonder about-ask them too.

(17) Tzvi, March 16, 2015 12:24 AM

author and source

Thank you, Gary, for the citation. Please also cite the book it's taken from: Bringing Heaven Down To Earth.

Keep up the great writing!

(16) Anonymous, March 25, 2013 9:12 AM

Thank you!

beautiful, inspiring.. I like your examples of "inner mazel tov tests". Dating presents opportunities to develop in ways that may be unnoticed by others. Thank you for sharing your insights. May you have a wonderful Pesach and merit your personal salvation soon.

(15) Anonymous, August 9, 2011 9:46 PM

Good attitudes, When we are doing all we can, it is so clear that Hashem will bring the right person at the right time.

(14) Nissan, April 26, 2011 5:24 AM

A Bracha

May Hashem send you your soulmate (and all those that are single) - the right person at the right time - and may He give you clarity and strength along the path of getting there.

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