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Ask the Matchmaker Rabbi – Lovelorn Edition

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Dear Matchmaker Rabbi:
When I was volunteering in Israel two summers ago, I met this amazing guy. It was love at first sight. Seriously — I tried not to meet him because I knew I was already in love with him! But we did meet, and there was no escaping it. When the summer ended, I needed to return to the U.S. to finish my degree. I told him I would try to return this past summer, but it didn’t pan out due to financial issues.

When I left Israel, I had asked him to come with me, but he said he couldn’t leave his life and family and Israel. I couldn’t imagine leaving mine in the States. Even though it’s been over a year since we have seen each other, we still e-mail regularly and every time I see his name in my inbox, I get really depressed. What should I do?

— Lovelorn in Bethesda

Dear Lovelorn:

There is nothing harder — or more frustrating — than having a love affair end because of geography! It’s impossible not to sit around and imagine how fantastic and romantic your life could instantly be for just a simple $1,000 planet ticket!

The reality, of course, is much more complicated. Your love, while undoubtedly very real at the time, did not have long to mature. With only three months together, you never moved beyond the exciting “honeymoon” phase to begin to test whether your love has staying power. What qualities in him (and you) would emerge if you spent more time together? Do you have enough shared interests and values to build a relationship over the longhaul?

And in one very crucial way, you already know that your relationship has a serious, fatal flaw: The desires you each have to live close to your families are utterly incompatible! If neither of you can imagine living your lives so far from home, there is no sense in investing more in this relationship. It was doomed before it even started.

Given it has been a year since you have seen each other and his emails continue to stir up painful feelings, I suggest you write him an honest letter and tell him what is going on for you. While there might be a time in the future when you can move from “lovers” to “friends,” your heart is not yet ready. For both your sakes, it would be best to take a break from communicating until you have had time to heal.

— The Matchmaker Rabbi

To ask The Matchmaker Rabbi a question, please email

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 in her fourth year of rabbinical school and the mother of 1.5 kids, nothing brings her greater joy than officiating a wedding. She is finishing a book on her dating adventures called Chasing Cupid, Tales of Dating Disaster in hookup Suburbia.

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3 Comments »

  • AlphaKid42 says:

    You are not ready to move to Israel and your image of him as the perfect guy is just getting enlarged out of all proportion. He is flawed. Everyone is. Tell him that you don’t want to converse any more, because it’s too painful for you to maintain the friendship. Wish him well and add his eMail to your spam filter. You’ll find another guy who is different but whom you’ll love, right at home.

  • lovenhim says:

    HI IM IN LOVE WITH THE ONE HE A DREAM COME TRUE…BUT HE HAS BEEN HURT BADLY BY OTHER WOMAN AND HAS TRUST ISSUES AND IS AFRAID TO SHOW ME HE CARE THINKING I WOULD Play HIS FEELINGS WHAT SHOULD I DO.. I CARE FOR HIM SO MUCH

  • ELMER says:

    HI MATCHMAKER,
    I HAVE BEEN WIITH 3 MATCHMAKER SERVICES W/ SOME MATCHS SUCCEESSFULLY, BUT NOT TO TIE THE KNOT! WHAT ADVICE DO YOU HAVE?

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