Dear Matchmaker Rabbi:

I really don’t know what I’m doing wrong with JDate. I’ve probably met more than eight, if not more, girls for dates, which is probably more than others. But the majority I have come across turn out to be psychos or obsessed with ex-boyfriends. We all have our standards and what we want out of a relationship, and I just can’t seem to find anything real.

I’m a young, attractive guy, a military vet, but I guess since I don’t have a Bachelor’s or Master’s degree like most 21-year-olds on here, they don’t want to talk to me. Sorry I was busy serving my country. I find that my only chance is for a younger girl since all the older girls won’t even talk to me unless I’m in their “age range,” and I’m 23, I have dated a 29-year-old, and a 36-year- old? So I just don’t know anymore.

It is intimidating talking to a very attractive girl for me because I always think ‘Why would she want to be with me?’ even though I myself am looking for an attractive girl just like that.

I started JDate after I separated from my wife in February 2010 , and its been one disaster or attempted relationship after another. I used JDate more as dating experience, and I have learned a lot, but I’d rather be another success story rather than writing this email. Any Advice?

— What Am I Doing Wrong?

Dear What Am I Doing Wrong?

The question “Why can’t I find someone” is the most common question I get and, having never met you, seen the emails you sent, or been a fly on the wall on your dates, it is nearly impossible for me to answer. But I can share some observations about your letter.

Your explanation of “what is going wrong” is extremely confusing and contradictory — so much so, it’s hard for me to know what is even true. On the one hand, you say you “can’t find anyone,” and yet you have only been on eight dates (which is nothing, by the way). You accuse these dates of being “psycho,” which is an extremely harsh thing to say, and it’s also very hard to believe. Sure, we all run into a “psycho” now and then, but to think that most or even many of these eight women met this criteria is a tad on the insulting side. Do you always feel this critically about other people?

You also accuse these dates of being hung up on their exes, and yet you yourself have only been separated from your ex-wife for 1.5 years, and it sounds like you aren’t even divorced yet! You cannot begin to be ready, emotionally, to enter into an open and loving relationship with a new person because you can’t possibly have “processed” your marriage, and its demise, in such a short period of time.

Have you had any therapy to talk about your feelings about the loss of this relationship, and what role you played, so you might do better next time? If you haven’t, you should begin immediately. I would be very wary dating a man who is not legally divorced, and who has not taken any deliberate steps to learn and grow from his experience.

Finally,  you give a whole range of “reasons” why you think your dates don’t like you, but I can’t tell what they are based on. You say it’s because you don’t have a college degree, but has anyone actually told you that? Then you say it’s because you aren’t their age, but you then admit you have had a date with a 29- and 36-year-old. So, that explanation doesn’t ring true.

Then you say it’s because you are shy and intimidated by beautiful women. That’s one explanation I find it easier to find some truth in. If a guy is acting shy, awkward and unconfident on a date, that is one of the surest date-killers there are. Men also value women who seem happy, calm and comfortable in their own skin — but that is particularly true the other way around.

It sounds like you have a lot going on inside of yourself, my friend, and you need some professional guidance to help sort it out.

— 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. Dude, you’re 23. Date women, enjoy them, get to know them. Don’t focus on finding something “real” at this point in your life, because it’s simply a fantasy you’ve built up in your mind.

    Learn to appreciate women for the unpredictable, exciting, flawed, beautiful creatures they are first. Once you do, you won’t expect some fantasy, and will have the knowledge about yourself, and women in general, to handle the right one.

  2. Hey guy. First, thanks for serving our country. It’s a admirable profession, even if the idiots in DC keep making needless war.

    Now, there are two aspects to dating that are important in what is essentially a pairing-off game. First, there are the things you bring to the table including your looks, your education, your skills, your income, your sense of humor, and of course, your dating skills. Second, the size of the dating pool in your area for women that meet your requirements, including appearance, size and weight, education, income, religion, politics, have kids, want kids, etc.

    For the first thing, you can most easily work on your appearance and your dating skills. Lots of books on Amazon for those things. Also, if you can take the brutality of it, ask you failed dates to tell you why they lost interest. It’s gonna hurt, but the information can be quite valuable to help you make yourself the best you possible.

    For the second thing, if you’re looking for a young Jewish lady in Swamville, then forget it. If possible, move to a major city, NYC being the best for the largest population of single Jewish women. She’s out there. Just increase your odds of finding her.

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