Dear Matchmaker Rabbi:

I have been dating a man who I think is wonderful, and I am very attracted to him.  We have had six dates, and they have all been highly successful and fun; we get on well together, and share a lot of interests and similarities.

He is affectionate toward me and asks me out an average of once a week or once every two weeks, but rarely from one date to another. I am always surprised when he does call or email me for another date.

He warned me he is not ready for a commitment in his life and also that he is a slow worker. I know he likes me very much, as I do him.  I am ready for a committed relationship and  just wonder if I should broach the subject or just let things go on, dating now and then, when I really would like to see him and be with him more. 

I am afraid of frightening him away if I say something, yet he said he is a slow worker and perhaps he needs a shove.  He said his ex-wife proposed to him as she got tired of waiting …

What do you suggest?  We are both in our early 60s.

— Should I Wait or Should I Go?

Dear Should I Wait:

When people tell me “where they are” emotionally, and what they want, I am inclined to believe them. In this case, he said he doesn’t want a committed “full time” relationship, and he is acting like someone who doesn’t want a committed full time relationship. Both his words and his actions are in line with each other, so I suspect it is your hopeful thinking that is making you consider proposing more.

I don’t doubt that he genuinely likes you and likes your time together. But it is also possible to really like someone, love their company once a week, and not want something deeper than that.

There is nothing wrong with you asking for something more of him. That is where you are at, and what you want – and verbalizing your desires is always a healthy thing to do. But you should be prepared for the likely answer that he is not interested, and the real possibility it will “scare him away,” as you say.

If you really do want to tell him, go for it! Perhaps he will be less likely to be wigged out if you explain to him that you realize he probably doesn’t want more — and that that is okay with you too. Of course, you can only assure him of that if it is actually the case. If you keep seeing each other casually, and it starts to feel like torture to you — then ending your association with him would be the best and kindest thing you could do for yourself.

Whatever you decide to do — ask him for more or don’t — I have one request: Don’t just sit around and wait for him to ask you out. You should be doing the same! Call or email him sometime and suggest a theater show you’d like to see, or a new restaurant you’d like to try out. Once you’ve had six dates, women should definitely be doing their share of the asking. That small act will help you feel less like you’re a passive player in this romantic friendship.

Good luck!

— 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 Jewish Suburbia. You can follow her on Twitter at @wanderinghebrew.

  1. i’m 67, he’s 64. i’ve lived in area 34 yrs. he just moved to area 5 months ago. we started emailing from a dating , lot’s of dates. him, i was first person, locally to show interest. move ahead 2 months, lots of dates. ….and intimacy…he asked for mutually exclusive status. i absolutely agreed. his last relationship eneded a year ago, mine 2 yrs. ago. WHAT IS CONTEMPORARY RELATIONSHIP TIMELINE GUIDELINES??? thank you

  2. There’s no hedging your bets here.
    You can’t have your cake and eat it too.

    You can either accept what you have now, as is, or you can attempt to move it forward and risk damaging it forever.

    A man I know asked his date to go steady. She said it’s marriage or nothing. He asked her to marry him. She did. I’m evidence of that marriage. He might have said no, and I wouldn’t be here to write to you. That’s the chance she took.

Leave a comment

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