Dear Matchmaker Rabbi:

I am 29 years old, and I still have yet to have a real, meaningful long-term relationship.  I feel like every guy I have dated is “unavailable” in one way or another; hat is the type of guy I am drawn to and/or is drawn to me.

I really want to settle down and meet a guy who wants to be with me. But every guy I meet can’t seem to handle me or is not ready for me.What am I doing wrong? Is it bad to want happiness and love?

– Frustrated
Dear Frustrated:

Anytime we can’t find or achieve something we really want, it’s hard not to get discouraged. But try to keep some perspective. The average age of marriage for men today is 28 — which means half are older than 28. Also, the more education a person has, the later it is he or she will probably marry. You are still well within the “normal” range that life partnerships happen these days.

My best advice to finding that special someone is first and foremost to focus on yourself. Find joy and meaning in your single life; pursue your hobbies and friendships; look honestly at your own bad habits and baggage, and do all you can do to be “ready” when that special someone does appear at your door.

Also be clear about what you are looking for and communicate it clearly with the men you meet. If, after three months, the relationship doesn’t appear to have staying power — don’t stay in it. That, I think, is the biggest regret I have about my own dating life.

— The Matchmaker Rabbi

To ask The Matchmaker Rabbi a question, please email

Joysa Winter, aka The Matchmaker Rabbi, knows all about how hard it is to find lasting love. It took her 17 years to find Mr. Not Wrong! In that time, she tried just about every singles site, dating club and Matzah Ball known to humanity. Now a rabbinical student and the mother of 2 young kids, nothing brings her greater joy than officiating a wedding. She is finishing a book on her dating misadventures called Chasing Cupid, Tales of Dating Disaster in Jewish Suburbia. Read more about it at
  1. First of all: How can you ‘officiate at wedding’ when you’re a “rabbinical student”?

    Second and more to the point of answering the question of this woman: You gave her the standard women’s rhetoric and not the answer she needs to hear! In other words the answer she and most women want to hear and not what they need to hear. Now, women know women but only men know men. There are many men ‘gurus’ who also tell women what they want to hear but that just keeps modern women single. Men are simple relationship people and women are complex relationship people. This particular woman has to first recognize her own limitations (as we all do) and then get into a man’s head. Just do what her grandmother’s did to get a man would have been the best answer but not the PC answer.

  2. The dating and marriage attitudes that permeate English-speaking countries are particularly self-destructive. You’re working against a culture of paranoia, entitlement (for women), and excoriation (for men). One thing you can practice is self-enlightenment, and cease thinking so much of yourself and your situation, particularly if you have established a project timeline for your key life events. Hothing turns men off more than a woman who runs her life and relationships like project milestones with deliverables.

  3. Hi there,

    “unavailable” just means they’re not that into you. There are plenty of dudes out there who would love to settle down with you. Try giving some of the guys you’ve turned down a shot. Plenty from that pool will be more “available”.

  4. I think that the best attitute to have is that everything happens at exactly the right time. If something does not go as you want, that does not mean that you are doing something wrong, only that it is not meant to be at that point in time.

    Also, I agree that you should focus on enjoying your own life. To say that you will be happy when some certain thing happens, is not a good way to live. Right now, you only have the present moment.

  5. Sweety it’s not you, but it is your selection. Take a look at how you present yourself and ask if your are presenting a woman who is ready for marriage. Then try a different dating approach. Don’t have a list or requirements but date whom ever is interested. Sometimes the “one” is right under our noses. Sometimes we have to reach out further than our surroundings. Basically from a psychological stand point like attracts like. Good people do attract jerks but if your confident then you will recognize them coming from a mile away. Have some friend tape you on a date and then review it at home. Are you smiling? Do you look engaged in the conversation? Is it obvious your uncomfortable or nervous but it is being read wrong? These are things we all do but are rarely aware of. Be honest about feeling nervous if you are and they will have less chance to “assume” what you feel. And when asked what your looking for be straight with that as well. Honest is a good integrity booster and who knows he may have a friend your perfect for. Just stay away from the “usual” stuff that may be safe and go for different. Good luck hun I hope this helps!!

  6. I fell ya. Amanda’s advise is good, and it’s true that it’s your behavior, not “you,” but to others, these are the same thing. The good news is, you can change your behavior.

    Start with information gathering. Contact each of your failed dates and ask them for a few minutes of their time. Say that you want them to be completely honest with you, and tell you their impressions of you, and why they lost interest.

    I’m not gonna sugar coat this — that exercise is gonna hurt. Make sure you have a friend at hand to talk with, so you don’t go over the edge. Remember to keep things in perspective, ‘cuz these guys are the ones you know rejected you, not an objective sample of the guys out there. Expect the worst.

    Now, with the information you gain from asking, you can decide if their impressions of your appearance and behavior are the images that accurately reflect who you are. If so, then you simply need to find a different way or place of selecting dates. If not, you can ask other people, girlfriends and potential dates, how to best appear and behave to project the particular impression you want to show.

    I know, it’s strange advice, but “What’s wrong with this picture” is how I suggest approaching it. Just have chocolate, tissues, and a friend with you when you explore, and know that you are not a bad person — you are likeable and loveable.

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