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    Dating and Relationship Advice

    Dear Rabbi and Shira, I love your column each week. It’s the first thing I read in The Jewish Vues once I pick it up on my way home from work. I’m hoping you can help me. I am dating a guy right now for a month who is fun loving, smart, and genuine about his religious beliefs and practices. The problem is he has a sketchy past. He did things that I would have never done or can even imagine myself doing. Although I know he is sincere and is where I would want him to be religiously now, his past really bothers me. Should I continue dating him or move on? 

    -Sketchy in Cedarhurst 

    Dear Sketchy in Cedarhurst, 

    Thanks for writing in. We appreciate your kind words about our column. We would like to ask you a few questions. What part of his past makes you feel uncomfortable? Is it because you’re so frum or innocent that you can’t conceive of someone doing something wrong? Jealousy that he “tasted” something you can’t? Does his past make you curious about his experiences, and you feel it’s wrong for you to think about it? Are you afraid of him returning to his previous ways? Regardless, in the end, only you can decide whether or not you are comfortable with his past. As you did not leave many details about his past here are some reflections and questions. Does he come from a non-religious background? Did he grow up in a similar background to you but temporarily lapsed in his practice? Do either one of these questions have different implications for you? Remember, that part of teshuva is moving forward with life and becoming the best version of yourself. Consider who is he as a whole. He is not what happened in the past, he is who he is now. What are the choices he making NOW with regards to parnassa, learning and growth? What type of home does he want? Think about it. He could have chosen any other lifestyle, adopted any other way of life. Yet he decided to live a frum one. At the same time, there are other life experiences and choices which can have lasting impact. Health, psychological, substance abuse or legal issues may present more significant challenges that might hinder you from moving past his past, and for you to accept him. You are the only one who can decide if he is right for you. You might be uneasy about his past at first, but learn how he’s made peace and is moving forward. Maybe you can too. Remember and try to appreciate that the man you like today is only that person because of the challenges and setbacks that he experienced. Can you let go of his past? If you can’t learn to accept his past, then it’s probably a good idea to end this relationship. The choice is your hands. 

    -Rabbi Reuven and Shira Boshnack