Dear Matchmaker Rabbi:

I started dating a man five months after his wife died. They had been married for 17 years. He said he was ready to move on and love again. We both knew there was a connection. I fell in love with him, and he told me twice he loves me. Everything was going GREAT!

Well, I woke up this morning and suddenly his story had changed. He asked me to give him a break for a few days to think things over and “see what happens.” He thought he was ready to move on, but now he thinks he is not.

Last night, he was making plans about getting a small business going with me; today he wants off. I am so hurt and confused, I don’t know what to think. My best friend said she thinks he has feelings for me, but he’s just scared and has a lot to get over before he can move on. Please help me if you can. Thank you!

-Hurt & Confused


Dear Hurt and Confused:

I don’t blame you for feeling confused, but I especially don’t blame you for feeling hurt. Who wouldn’t be? It is obvious that this man is confused himself, and that is hardly a surprise either, given the circumstances.

Every person has a different time table for grieving. That said, generally speaking, people need at least one year after the death of a partner to really be open to a new love and relationship. This is the opinion of modern psychology, and it is also a benchmark in Jewish tradition. Judaism has particular mourning rituals it lays out for the first 7 days after a death, then the first 30 days, and then the first 11 months. After 11 months, we are encouraged to end our public mourning and re-enter the “regular” world.

In my opinion, 7 months was MUCH too early for him to be making the professions of love he made. No doubt he believed he was sincere, but they were wishful thinking on his part. While they may have been heartfelt in the moment, he hadn’t healed his own heart enough to really be open to partnership with you.

That said, the words and the relationship were begun. Happy marriages (or long-term relationships) have been formed after short grieving periods. Every person reading this column probably knows a couple that formed in short time frames after a death. It’s the exception, but it happens.

In the case of you two, I encourage you to find a relationship therapist as soon as possible. You need the help and objectivity of a third party to start sorting things out. In addition, I hope he would consider going to a therapist on his own, to better understand his own feelings.

Absolutely do not start a small business with this person. Emotional entanglement is one thing, but adding your personal finances to the situation? Absolutely not!

Lastly, be open to the possibility that he is using grief for his wife as an excuse for leaving a relationship that for whatever other reasons, he has realized he doesn’t want. I’m not saying this is the case — I’ve never met him — but it could be an “easy out” for him.

You said you love this man. Sometimes the greatest act of love is letting a person go. If he isn’t willing to go into therapy with you (for a minimum of six sessions), I hope you can find the courage and strength to calmly kiss his cheek, wish him the best, and walk away. You deserve to be loved in equal measure to the person you give your love to.

-The Matchmaker Rabbi

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Joysa Winter, aka The Matchmaker Rabbi is finishing a book on her 15 years of dating misadventures called “Chasing Cupid: Tales of Dating Disaster in Jewish Suburbia.” Need help writing your profile, or dating advice tailored to you? Email to learn more about pricing and services. You can also read Joysa’s blog on Jewish and interfaith weddings, as well as other progressive Jewish topics, at

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