Alanna: We’ve all been asked some pretty personal questions on dates and for some reason we feel obligated to answer them.  There is nothing you have to answer if it makes you feel uncomfortable.  A friend of mine suggests smiling or saying, “Why do you ask?” after an inappropriate question.  It’s completely fine to answer briefly and vaguely in the initial stages of dating.  You may also say, “I’m not comfortable answering that just yet” if pressed by your date.

Onion Layers

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Gil: I think there are parts to every person that should not be shared right away. As your relationship develops, you will know if it’s safe to discuss what has happened in the past. Be yourself, of course, but careful, at least at the beginning.

Alanna: I recently read a dating book where the author suggested that we reveal ourselves on dates as if we are peeling an onion.  Since we are multi-faceted people and don’t want to unload a whole lot of information, it’s helpful to reveal yourself slowly.  There are those who say you should be completely comfortable acting like yourself and say whatever you would like – I’m not so sure that’s a great idea.  I’d like to leave my dates wanting to get to know more about me on the next date.  If really personal information was exchanged, if the discussion revolved solely around deep issues, or the date was not fun, chances are there won’t be a second one.

Save The Litigation For The Courtroom

Alanna: Nobody likes to be cross-examined, especially on a date, so it’s best to ask the questions you feel you need to ask in a covert manner. I was recently asked on a first date 1) what I felt were my top three qualities, which was followed up by 2) exactly why I wanted to be in a relationship, and 3) what I felt I had to give to someone.  If these questions had come up casually in conversation, in a give-and-take method, I wouldn’t have been on the defensive.

Gil: Dating should be fun. Take your time, and go with what’s presented. All your questions will be answered in due time. Have emunah that you will know what you need to know. It’s all part of the process. Feedback About A Date

Alanna:  A lot of people, including me, myself have discussed an entire date with several friends. The problem with this approach is that each friend has a different perspective, personality, past experience, and way of doing things.  I’ve found it helpful to have one good friend that I get dating advice from.  If you haven’t found that person, look for someone who has proven him or herself to be objective, but with your best interests in mind.  You can start by asking for advice about something small.  The advice you get should resonate and make sense, even if you’re not comfortable following it (although you know that you should).

Gil: It’s really important for you to have a team to bounce off of while dating. Someone with whom you have a relationship and an intermediary who can help filter some of the questions. It’s not easy to find the right person, but someone you have a strong relationship with, and who has your best intentions in mind, is a great place to start. I have found that it helps to speak to people who have gone through the same experiences, and have come out the other end.

Red Flags

Alanna: I recently asked Facebook friends to anonymously list red flags on dates. I received 80+ comments. What a heated topic! A friend of mine said that her date gave very specific instructions for preparing his meal, ate most of it, then complained and refused to pay. Another friend experienced racist and sexist jokes. Yet another had a date spend large periods of time talking about himself.


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Gil Poznanski is a baal teshuva who left the Hollywood film industry to study at Aish HaTorah in Jerusalem, Israel in his 30’s. A teacher and media creator, Gil has a passion for communicating and telling a great story that led to his interest in Torah and Judaism. Currently he is teaching technology to the public in Melbourne, Australia, where he is constantly breaking stereotypes and stretching the expectations of religious Jews in the public sector. He can be reached at [email protected]. Alanna Fine lives in Los Angeles where she’s completing her MSW. She looks forward to no longer having the expertise to write dating articles. Alanna can be reached at [email protected].