Dear Matchmaker Rabbi:

I’m in love with “The One.” He is a dream come true, but has been hurt badly by other women and has trust issues. He is afraid to show me he cares, thinking I will hurt his feelings. What should I do? I care for him so much.

— Where To Go Next?


Dear Where to Go Next?

I’m happy to hear you think you’ve found “The One,” but I’m concerned that you might be coming up with rationalizations to explain behavior on his part that is less than what you deserve. You deserve to be with someone who is as psyched, thrilled and jazzed about being with you as you are with him!

How do you know he is distant because he has “been hurt before” and not because he’s just not that into you? Did he tell you that, or are you trying to come up with “answers”?

Even if he is afraid to trust people — and hey, who isn’t afraid to trust? — if he really likes you, he will be actively trying to get over his fears. Is he at least taking small steps to build trust with you? Is he in therapy to work through his old heartaches? Is he talking with you about ways you two can build intimacy without triggering his fears?

If you answered “No” to all of those questions, please, for the sake of your own heart and dignity, move on. He’s either not that into you, or he’s not ready. Either way, you deserve more than that.

— The Matchmaker Rabbi

To ask the Matchmaker Rabbi a question, email her at

Joysa Winter, aka The Matchmaker Rabbi, knows all about how hard it is to find lasting love. It took her 17 years to find Mr. Not Wrong! In that time, she tried just about every singles site, dating club and Matzah Ball known to humanity. Now a rabbinical student and the mother of 2 young kids, nothing brings her greater joy than officiating a wedding. To inquire about hiring her for a Jewish or interfaith lifecycle event in the Philadelphia area, or to read her blog, visit Her book on her dating misadventures, called Chasing Cupid, Tales of Dating Disaster in Jewish Suburbia, is looking for a publisher! Read more about it at
One Comment
Leave a comment

Your email address will not be published. Required fields are marked *