Dear Matchmaker Rabbi:

I like that JDate has quite a variety of widows/ers. It is actually a bit overwhelming. I do  prefer to date a widower because … they get it. What I’m a little blown away with is: I have been contacted by a man 12 years my junior who has been widowed for two years, (I’ve been widowed for less than two years.) We seem to have that cyber sense/connection. Thank goodness we are thousands of miles apart and can whittle through this and take time to get to know each other!

I know for me this is an attractive distraction from other feelings that I am confronted with daily. But what the heck does a young man want with the likes of me?!? I did not reach out with the initial contact.

— Why Me?

Dear Why Me:

Why not you? Men develop feelings for women 12 years younger than themselves all the time. Isn’t it nice to think there might be a mensch of a guy out there who is open to feeling love for a woman 12 years his senior?

Who can say if this will be become a romantic love match? The fact you are so far apart geographically makes it unlikely. It’s very hard for any long-term relationship to happen with geography like that, simply because you can’t spend day-to-day time together. BUT there are certainly plenty of people who have united their distant stars with smashing success, so never say never.

It also sounds, though, like a love match is not what you are really ready for right now (and maybe he isn’t either). Maybe what this connection is about is friendship, emotional solace, and even the healing energy of flirtation. You may never meet, but what you do have is an e-friendship that is helping you both move through a painful place.

My thought is, don’t worry about what he might want “with the likes of you.” Simply try to enjoy what is — whatever that may be. Be kind to yourself, and hold the memory of your lost sweetheart dearly. As my godmother, Jennifer J Martin has written in her book about loss and love: “Grief is a harsh mistress.” It takes tremendous courage to let her in.

Any connection we can make to help ease the pain is a connection worth having.

— The Matchmaker Rabbi

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. She is finishing a book on her dating misadventures called Chasing Cupid, Tales of Dating Disaster in Jewish Suburbia. Read more about it at
  1. Long distance relationships do work! But it takes two consenting partners to agree to it. Men fear that they are obligated and need to make up their minds quicker, rather than drag it out and keep a girl guessing. The same applies to a woman. You are either interested or you are not. Long engagements don’t guarantee a lasting marriage either. It is the risk that you take in life, as long as you have a positive attitude. I agree that people who have been burned in the past are a lot more reluctant to making a fast move, but you can’t hold that against the next person that comes along. It’s strictly mind over matter and if one person is willing to relocate and make a life with a new love, why shouldn’t long distance work? AllSmiles018

  2. From a man’s perspective:

    You’re both widowed only two years so it is only a matter of exploring the dating world. Distance can be a problem but for mature singles the dating pool is tiny in ones’ own community. Fact is that men want older women for the main reasons of sex and/or mothering. AND older women’s main reason for wanting younger men is to feel younger and it is more acceptable to be rejected by a younger man. Men have always dated younger women and always will, women Lip, immaterial. It is the Biological age that is significant and not chronological age.

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