excerpts from an excellent article on this topic
Shidduch Narratives: “Disclosing,” or Sharing a Life in Context
by Dr. Benzion Sorotzkin, Psy.D. Clinical Psychologist on www.drsorotzkin.com

…how and when to reveal information of this sort? We seem to be stuck with a difficult dilemma.

If one reveals the problem before the relationship develops it will usually result in a “no.” 

If one waits until a relationship is already established, then the shock of the incongruous revelation and the resentment over the deception can lead to an angry break up or a resentful acquiescence.

To me, the term “disclose” seems more appropriate when selling an object, such as a used car. The seller is obligated to disclose to the potential buyer that the car often overheats on hot days, for example. It seems to me out of place when discussing a person. One “shares” information about himself.

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It is preferable to begin at an early stage of the dating process to gradually speak about the challenges one faced in life. It should be presented as a positive attribute of facing and overcoming challenges.

(I compare it to how someone would speak of arriving in America as a penniless immigrant and having to initially work as a janitor. Then, by dint of hard work, he learned English and learned a trade and became successful etc. He would tell over the story with pride and not with shame).

The story unfolds in a gradual and integrated manner and creates less of a shock because the narrative flows smoothly and is told within a positive framework.

Sharing the causes and history of one’s challenges, how one learned to cope with his challenges and his accomplishments in the face of adversity is more meaningfully informative than a dry description of his symptoms. It also provides the necessary context to get an accurate picture of the complete person.

The fact that the person didn’t react passively to the challenges in his life, but rather took the initiative to improve himself by developing a close relationship with a rebbi, undertaking psychotherapy, etc. will be seen by many dates as admirable qualities.

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The positive way the date reacts to earlier stages of relating to the challenges he faced will increase his level of confidence to further share details of his life.

This process of gradually sharing more details of one’s life is a compressed version of what happens between close friends. They didn’t share all details of their lives when they first met. Rather, over time, they gained confidence to be more open with each other based on the empathic reactions they received to their earlier revelations.

If the fact that one faced these challenges is unacceptable to the date, then at least it will become apparent at an earlier stage and the person can conclude that it’s not a suitable match without divulging too much information.

I also suggest that after the person discusses the challenges he faced in his life he should ask his date if it’s ok for him to ask what might be some of the challenges she had to deal with in her life.

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This serves to make the relationship deeper and more meaningful and also equalizes the two sides; both imperfect humans who should take pride in their efforts to grow in the face of challenges.

When the narrative of a person’s life is told in a gradual and integrated manner during the dating process, as suggested above, it will become clear to the date how the difficulties are the result of life experiences and not inborn disorders. The person can also articulate what he has done and is doing to deal with, and even grow as a result of, those difficulties. While this is most certainly not a magic formula that eliminates painful rejection, it does increase the likelihood of success.