Dear Matchmaker Rabbi:

I am everything a man could want: outgoing, witty, warm, caring, fun, educated, athletic, confident, musician, professional, mentally and financially stable. I’ve been on every website, dated lots of men, gone to many single weekends, but I just can’t find the one.

I feel it’s because perhaps men feel intimidated by me and my accomplishments; they don’t want to travel to date; they are commitment-phobics; they are not mentally and financially stable. What should I do?

— Dream Come True


Dear Dream Come True:

You didn’t sign yourself ‘dream come true’ but I’ve given you this moniker. Why? Because I believe you. You probably are a guy’s dream come true!

Are there a lot of men who feel intimidated by outgoing, successful women who are not emotionally needy and who won’t become financially dependent on them (and hence … easier to control)? Absolutely there are.

Do some men not want to travel to date? Sure. (Probably an equal amount of women don’t want to either. Long distance relationships are difficult to maintain, and they also create a big hurdle in really getting to know the other person.)

Are many men commitment-phobics? Absolutely they are. Some women are too, but far more men than women seem to have this problem. (I don’t know why this is by the way, and given that we women still primarily fill the role of child-rearing, it’s a question I think we should start seriously asking ourselves when we become parents. Why are so many men growing up without understanding the rewards of family, partnership and commitment?)

Lastly, are some men not mentally or financially stable? Sure. But you don’t want those guys anyway, so cross them off the list.

In answer to your question: “What should I do?” — you should keep on trying. You don’t need to find a football team — you only need to find that One Special Guy who isn’t a commitment phobe and who won’t find you intimidating.

In the meanwhile, as you are looking, you should also be fair and put yourself through a critical self-assessment. You think of yourself as “fun” and “outgoing” — are you sure that doesn’t slip into being overly loud or obnoxious sometimes? You are proud of your career success (as you should be), but do you take care to not be flashy about it and to be modest with your achievements? That’s a nice quality for men, not just women, to have, but acting overly self-confident seems to rub men in particular the wrong way.

My point here is that none of us is perfect. Keep trying, don’t change in any fundamental way, and don’t, for goodness sakes, “settle.” But at the same time, be honest with yourself.

Get some feedback from close friends and even guy friends about what ways you might be inadvertently sabotaging yourself. There are a few great books out there that can also help you do that. Calling in the One by Katherine Woodward Thomas is one that comes to mind.

— The Matchmaker Rabbi

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. To inquire about hiring her for a Jewish or interfaith lifecycle event in the Philadelphia area, or to read her blog, visit Her book on her dating misadventures, called Chasing Cupid, Tales of Dating Disaster in Jewish Suburbia, is looking for a publisher! Read more about it at
  1. I know it can be confusing at times, especially why most men today seem to be commitment-phobic, but I think a lot of guys that are looking for the right woman to marry, are afraid that they are going to be settling for something good, when there could be something great out there.

    Is this right to do? Not at all. All that is being done by that is limiting the potential that the two of them have to grow together.

    I personally don’t care if someone is next door or across the country. In a world that is filled with such potential, ANYTHING is Possible! If that is the case, why limit yourself when it comes to matters of the heart?

    Finding that right girl or guy isn’t going to be easy, but if you keep believing as I do, it will happen.

  2. Dear Dream Come True,
    I think that it is not your accomplishments that men are intimated by but rather your behaviour. Since you are so accomplished, I am guessing you are quite aggressive (probably without even knowing it).
    You come on too strong and that freaks them out!

  3. I’m glad I found this article!!!!!

    All of our lives we are told that we should be more confident in ourselves and that we should all pursue our dreams and learn to be more out-going, friendly and approachable. But let’s all be honest here, once you become any of those things, it makes your life a living hell. People tell me all of the time that I am very attractive. For a long time, I never believed it. It was also hard for me to consider myself a smart person. Until one day I decided to accept my self for who I was. I built up my own confidence so that I could stop wallowing in my own self-pity. I wanted to be happier and nicer to myself so I accepted that I was beautiful and smart. To my surprise, once I accepted that I was in fact beautiful and smart, people began to hate me for it. My friends became envious, coworkers didn’t like me, guys didn’t want to date me. It became a complete and total nightmare! And I never talk about myself as if I am the best thing in the world. I just have normal conversations with people. A guy that I used to date told me that it wasn’t about what I was saying, it was the fact that I spoke and walked with such confidence and it was intimidating, especially since I was attractive. And here I was, spending all that time trying to improve myself for me, just to find out that everyone hated me for it. Guys would tell me that they really liked talking to me because I was interesting and outgoing yet they would leave me for women who were shy and uninteresting (my words,not theirs). And what was even more annoying was that they would complain about how uninteresting and boring their new girlfriend was but they never left them. It’s all really interesting to see that what people say they admire is actually what makes them nervous, fearful, envious, and jealous. Men feel like they aren’t needed when they meet a women who is confident and women feel insecure around women who are confident. At this point in my life, I feel like it would be best if I learned to not like myself anymore and become more introverted. Then I will be less threatening and everyone will be my friend. People liked being my friend and encouraging me when I was insecure. Men liked dating me when I was insecure. It is the complete opposite now and it makes me feel sad and alone. Its like I’m only allowed to talk about my problems because if I talk about how awesome my life is, everyone calls me self-centered or accuse me of bragging. Even if you aren’t bragging, its like your not allowed to be happy about your life around other people. And what makes all of this worst is that I can never talk to anyone about how much this hurts me because people think I being self-absorbed when I say that people are jealous of me or that men prefer women who aren’t as confident. I’m not even allowed to even talk about this for the fear that people will turn their nose up at me as I’m not allowed to be hurt by this or as if it is all in my head. I wish people could at least try to see it from my perspective.

Leave a comment

Your email address will not be published. Required fields are marked *