Inventory Check

Alanna: After a handful of dating years, I found it helpful to review my previous relationships and analyze what I was attracted to in the people I dated, what worked and what didn’t. I noticed some patterns and acknowledged that there were certain characteristics I was initially drawn to. Sometimes we date the same kind of person over and over again until we realize that we need someone completely different. It’s difficult to break out of a comfort zone and be open to dating a type of person we had never considered before. Once I took stock of my choices, I focused on what I’d do differently in my next relationship and concentrated on shifting the focus to really view the potential in my dates.


Gil: While it’s interesting to review prior relationships, we can often see issues in others through our past experiences, hopes and fears. People are generally attracted to the things they are looking for within themselves. A list of “deal-breakers” is a great place to start. Always be open to what the journey has planned for you, but don’t write someone off, unless you are completely sure he or she is not appropriate. Some of the most meaningful lessons come in surprising packages. However, if you know you’re not attracted to your date, or that he or she has a characteristic you’re not willing to work with, don’t hang on. Finish the date, be polite and move on.

Safety First

Gil: Always make a date in a place where you’re both going to be comfortable. Remember, when you first go out with someone new, it’s really a screening date. Both of you will be using the date to gather enough of an idea of who the other person is. Be yourself, be comfortable, and enjoy the flow of the date.

Alanna: When meeting a date without checking out references, one needs to be appropriately cautious; it would be safer to meet in a public place and drive there separately. Just like I wouldn’t go to an important business meeting without checking to see if my potential partner is upstanding, reputable, and has the qualities I’m looking for, I wouldn’t go on a date without checking those same things.

Dating Conversations

Alanna: So many of us go on a date without a plan or roadmap. One topic that can help open up the conversation is travel. It fosters a sense of adventure and excitement as well as creating a forum for shared experiences. You can also ask about his or her dream career, favorite place, or even crazy dating stories. I’ve found that the “what do you do for fun” question doesn’t really lead to much more than a list of activities.

Gil: If you don’t have anything to talk about, it might be worthwhile to have some set questions and subjects. Breaking the ice can be difficult and you don’t want someone to think that you aren’t a person of substance just because you got a little tongue tied. There is nothing wrong with asking friends to suggest some topics they have had success with.

Twenty Questions

Gil: Asking questions is a great way to get to know more about someone new, and tone is an important factor. Keep things light and fun. Always throw in a laugh when asking a deep question. I used to ask my dates: “If you were the richest person in the world, and didn’t have to work, what would excite you to get out of bed in the morning?” Most of the people would look at me with a blank stare and claim not to understand the question! I realized very quickly that the question was way too deep for a first date. When in doubt, a quick joke and a smile can go a long way. I also like to take note of what my date asks me and use that as a place to begin.

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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].