Dating Best Friend's Ex-Boyfriend

Hello, I’m a modern Orthodox Jew living in a small city. I'm currently facing a moral dilemma. I’ve developed feelings for a Jewish man, will call him Joseph. We met in college and is the ex-boyfriend of another college acquaintance, we will call her Sarah. I met Joseph through Sarah while they were still dating. Me and Joseph never really spoke while they were together, and we never really had classes together before. This semester me and Joseph started having classes together thus organically started speaking. Joseph told me that him and Sarah broke up. Although I'm Shomeret Negiah, recently Joseph and I have been spending time together, and there’s a clear romantic tension that evolved between us. I’m feeling guilty about this situation, as I worry about how Sarah would feel if she knew. I want to be respectful of her feelings and the trust she placed in me. I was direct with him about my discomfort and told him its best we dont speak. He was very understanding and very apologetic. Although there is no Halachic probation in what I've done, I'm wondering to myself if I did the right thing. He is a great man with great middos, and ultimately there is very few Jewish dating options for me where i live. I sort of cut something that could have evolved under the right circumstances, because i wanted to follow "girl's code". Is it morally wrong for me to have feelings for him, and was cutting the friendship between me and him the right thing? Ultimately, I also don't know how to move my friendship between Sarah forward. As the only heavily practicing Jew on campus, i put a lot of weight and meaning on myself to be a sort of shlicha. I always make sure that the few jews of our campus find places to celebrate holidays, and it is my ultimate goal to develop meaningful connections with them. Thank you for your guidance.

Shalom!

Thank you for your question.

As a general rule, Orthodox Jews customarily have a “middle-man,” known as a shadchan (matchmaker), to help with such details. 

There is nothing ethically or morally wrong in dating a friend’s former boyfriend. That’s exactly what happens in the “shidduch world.” When a couple has gone on a date and then, for whatever reason, decide not to continue dating, each one then pursues someone else. The final match is sometimes best friends and their ormer dating partners. There is nothing to worry about here. If you think he would make a good husband to build a Torah home with, then you should pursue it. It might be appropriate to inform Sarah, though it is not truly necessary if the dating is done in a more orthodox manner.

It is amazing that you are a sort of “shlucha” on your campus! You should continue to encourage Jews to perform mitzvot.

Good luck with everything!

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