The longer I did online dating, the more I realized that the Jewish women I liked fell into distinct categories. Some were visually striking – zaftig, auburn-haired beauties who looked straight off the boat from Odessa – and others were intellectually appealing as graphic designers, teachers, artists or writers. And one group was truly remarkable for several reasons: rabbis and therapists. I contacted them, they contacted me, and the experiences and friendships left a big impression, as I detail in my new book from Coffeetown Press, A Kosher Dating Odyssey.

I group women rabbis and therapists together — and found them appealing — because they’re all passionate about what they do, Jewishly aware, open to contacting men they find interesting online (like me) and excellent conversationalists. They simply have a lot to offer in a relationship. Their careers influence their worldview and behavior to a higher degree than other fields of work, and my acceptance of their career issues made it easier for me to connect with them.

(A note on definitions: “therapist” is my catch-all term for a range of work, ranging from licensed social workers through psychologists to the rarified air of psychiatrists and psychoanalysts. While state licensing boards and insurance companies distinguish among them, I don’t.)

Now, I’ll admit right here that an astute shrink might ask me, “What’s the attraction to dating rabbis and therapists? They’re smart and attractive, but so are many other Jewish women. Why single them out? Are you working through some type of unconscious issues? What do you feel about this?”

After wrinkling my brow and going “hmmm” for a bit, I’d respond like this: “While both of my parents were Jewish, I was raised as a Christian in Texas, then embraced Judaism as a teenager. It’s a long story. I had a lot of insecurities about how ‘Jewish’ I really was and my lack of Jewish experiences and learning. I self-educated myself over the course of decades. If a rabbi found me worth contact, representing 4,000 years of Jewish learning, then I had successfully re-created myself. And I always viewed therapy as an intensely Jewish profession, sort of the secular equivalent of the rabbinate. Some women even combined both careers. So, yes, women rabbis and therapists carry great symbolic value in addition to their individual traits.”

Rabbis and therapists as dating prospects were as unpredictable as anybody else. Sometimes we connected, sometimes we didn’t. I wanted to form closer relationships with some, and those feelings were not reciprocated. Emails went unanswered, what seemed like promising first dates sputtered into silence.

For example, I once visited a therapist who I nicknamed Vendetta in the book. We both were enthusiastic about meeting and from our online communications (we never actually spoke until we met) I saw myself as the decent guy who could treat her well after a parade of dating misfits and wackos. She had the smarts and looks I liked (think, Odessa looks with a Ph.D.) so I was ready to give Vendetta a try. I took a vacation day from work to visit her for lunch and a tour around the big city where she lived, not far from New York. I thought we connected, but she soon wrote to say we lived too far apart and her life was too complicated. She made noises about staying in touch but she was just being polite. She’s long gone from my life.

The dating profiles of rabbis and therapists reflected the pressures they faced in their jobs. Along with criminal defense attorneys, rabbis and therapists often omitted photos from their profiles. They take care in how they present themselves given the possibility that congregants or patients might see them. That could complicate their lives as authority figures in public and very private rituals. While I often looked askance at profiles without photos, in their cases I understood. If we got along, the photo would follow.

Some downplayed or blurred their actual jobs. They wrote about “management” positions, and what is rabbinic work if not financial, organizational and spiritual management? I remember one attention-grabbing profile that said, “I’m a rabbi – don’t freak out!” I never freaked out – rather, I was curious about women in these positions and had no desire to exploit or disparage their work. I respected their devotion to their values. When I dated one of them, I was always happy to hear what was going on at the office, but I didn’t look at a date as a counseling session or a source of theological guidance. Dates could, however, revolve around professional activities, such as Jewish music events and breakfast at the annual meeting of the American Psychoanalytic Association.

Other men did, however, react oddly. If they didn’t exactly freak out, they became obstreperous or needy. I know because I asked a rabbi and a therapist (both of whom are JDate friends I’ve known for most of the past decade) about their experiences.

My rabbi friend said, “Mentioning I was a rabbi was always a way to stop a conversation dead in its tracks. I would go dancing as a rabbinical student and people wanted to tell me all their God problems.” And if a man didn’t believe in God, that sparked its own response as he had to explain why he wouldn’t date her: “Some were downright nasty.”

Some men couldn’t wrap their minds around the career obligations of a rabbi (think: “Shabbat”). One man insisted they have dates on Friday nights. She recalls, “I don’t go out on Friday nights not because I am a rabbi, but because I am a Jew.”

On the plus side, the online world worked for her. “The best thing is I met people whose paths I would never cross with in New York,” she told me.

The therapist friend, who appears as the Lark in my book, mused, “My initial response is that men are intimidated, and they mask this by joking ‘I’m sure you are analyzing me!’ A few asked the question seriously if I was. It’s hard to sort out what you do professionally from dating, because what you do does color how you see the world. Even if you aren’t formally analyzing someone, your perceptions of people are influenced by these skills. The men who seemed to say that the really did need a shrink and they were glad that I was one — those are the ones I keep away from! Mostly being a therapist gives me listening skills, and listening is crucial in dating. I’ve often thought that the history of a relationship can be predicted in the earliest contacts. Still, therapists have huge blindspots in regard to their own lives, and I am no exception.”

The rabbis and therapists I dated touched me with their high degree of empathy. They reached out to me in memorable ways. One rabbi, for example, knowing my ongoing efforts at Jewish self-education, provided me with a tefillin set that I use regularly at morning services at my shul in Westport, Connecticut. Every time I don the tefillin and say the accompanying prayers, I think of her, and I’ve let her know about the critical role she played in my spiritual development as a Jew. She gave me the tools to transform a daunting ritual into something I can now do with confidence.

Another rabbi, the one quoted above, invited me to join her and her friends and family at Passover and New Year’s Eve. I accepted and enjoyed myself (women rabbis really know how to organize a seder!). After compiling books that her children had outgrown, she gave them to my pre-teen son. We did the great book handoff in the parking lot of a suburban museum, and I drove away with several boxes of prime reading material, to my son’s delight.

Over the course of years of friendship, the Lark and I exchanged thousands of emails – I mean that literally – on our children, our dating highs and lows, our creative activities. The subject lines of emails hint at the topics: “Men, men, men and me,” “Southern charm,” “Feeling appreciated is a good feeling,” “No good deed goes unpunished,” “Conversation with XXX, about what I expected.” “Oh dearie dear, a JDate chat,” “Marketing Girl in touch,” “Here’s a great first date!” “Psychotic?” and “Bittersweet moment with the Ex, number 156.”

I found her work intriguing, performed at a very high professional level, but I always respected limits and confidentiality. We both offered insights into each other’s romance issues and I always treasure her as a caring friend who could size up a situation. I like to think I was the same, lending a male perspective.

I once wrote to her about a vexing romance, “You’re perfectly justified in not contacting him. If he contacts you, so be it, but you’re throwing yourself against an emotional cactus patch trying to get on track with him. He’ll always be ambivalent and dancing out of the way, until he wants to get his rocks off again. If you talk and even meet again, the whole time will be spent figuring out his issues, what he wants, his efforts to keep you on his terms while he slinks around with other women. You’ll get nothing joyful out of it. Bag and tag him and move on. I know you saw the warning signs of his character, and there are other, more worthy men anxious to meet you. Let him regret the amazing woman he’s lost at his leisure.”

She often gave me similar advice regarding women who didn’t reciprocate my feelings. After one woman said she wanted to talk to me about our relationship (you know what that means), then ignored emails and phone calls from me, the Lark replied, “She is really unkind. Maybe you should just write her a goodbye note? I know that’s not best, but she hardly deserves your time.”

The Lark appreciated my guidance, when she wrote, “Thanks for your supportive words about me and men men men. You are right – I have found a lot and at the same time, not enough.”

Emails like those volleyed back and forth for years – encouraging, consoling, agreeing, amusing. As our lives evolved we’ve eased off on the constant check-ins. After all, the Lark, the Rabbi and I are all in rewarding, stable relationships and have left the convulsive emotional highs and lows of online dating behind. We’ve settled down and there’s simply less day-to-day drama to ponder, less guidance requested. We’re just friends living our lives.

In closing, since our time is up for today, I’d like to mention a striking rabbinical quote that sounds appropriate for the situation, “Your true friend is the one that knows your faults and yet will love you.”

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