Dear Matchmaker Rabbi:

I try to write letters to women, trying to fit in with their interests. However, I strike out frequently. How do I improve my salesmanship? My social skills are wanting, and I am desperate for a match.


Dear Desperate:

You ask a great question! The rules of making First Contact via email (as one might quip on Star Trek) are a lot like the principles of good conversation. Don’t babble; ask questions about the other person; and share a little, but not too much, about yourself.


  1. Have a friendly, casual introduction and tone.
  2. Single out one or two things in particular that you liked about her profile. These should be things that might be points of shared interest or compatible qualities, rather than something that is, in the long-run, irrelevant.

For example, the fact you both like hiking and travel would be worth mentioning. The fact you think she has “pretty eyes” or is in an “interesting profession” is irrelevant.

  1. State a few details about yourself, which are not in your profile, giving her material she can use in a response.
  2. Use proper punctuation, capitalization and salutations, just like you would when writing an inquiry for a job.


  1. Don’t be too long. You don’t want to invest too much time writing any email; email is just meant to be an ice breaker, not a primary mode of conversation. If she is interested and responds, then you can start investing more time.
  2. Don’t despair if you don’t get a lot of “write backs.” It’s hard to believe, but most people don’t get responses! To ask yourself what you are “doing wrong” or wondering what you “might improve” is fine, but for many people, dating is a time and numbers game.
  3. Don’t sound desperate! Men and women alike can smell desperation a mile away, and it sends them fleeing. If I meet a guy who seems desperate, what I immediately think is: “Any attraction/interest on his part is not a reflection of something real he sees in me, but rather just a manifestation of his desire to not be alone.” This might not be true, but it is what the other person will think, and she’ll just ignore your contact.

To conclude, wrapping up all of my points together, here would be a great sample text:

Dear Hillary:

I came across your profile today on JDate and wanted to drop you a line and say ‘hi.’ (1)

I see that we both have a shared interest in travel and adventure. (2) Have you been able to take any trips this year? Six months ago, I made my first trip to Mexico with an old friend from college. The highlights were a jungle excursion and trying scuba diving for the first time. The fish were incredible, but the water was too cold. (3)

You also mention loving alt rock from the ‘80s.(2)  It’s hard to believe, but I went to a Depeche Mode concert last year; who knew they were still touring and making albums?! (3)

At any event, if you’d be interested in corresponding further, please let me know!


― The Matchmaker Rabbi

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