Dear Rabbi Singer:

I am a young looking 58 and recently divorced; just put my toe in the water.  The men who have things in common with me, in my range, 54-68, don’t seem to make the first move.  Is it a good thing to “flirt” on JDate if you are sincere?  A few men well above my range are “looking” at me, I can diplomatically deal with that.

Also, I think JDate as a whole should remind people talking about exes too soon is a deal breaker.  There’s time for that, and we should remember we learn something about love from every relationship.  Todah for the wonderful work you do!

Dear Lenore,

I commend you for reentering the world of dating. I’m sure it’s tough, but well worth the effort. You’d think that men in their 50’s and 60’s would be done playing games and be ready to pursue their romantic interests in a direct manner. Unfortunately, not all are. Those are the ones that you don’t want to waste your time getting involved with in the first place.

I’m assuming that you’re looking for a mature man to have a healthy and meaningful relationship with. That kind of man will not be put off by a message from you that lets him know you’re interested in getting to know him. I don’t know of too many men, regardless of age, who will ignore a message from a woman they find attractive, unless they’re not interested in dating at all (in which case they probably wouldn’t be spending time on JDate).

As amazing as the content of your message may be, your potential suitor’s response will depend primarily on your profile, particularly your photo. That’s how guys operate, even when they’re collecting social security. So it’s your job to make your profile and photos as attractive and appealing as you can. Your JDating® success depends on them.

Bottom Line: There’s nothing wrong with contacting or “flirting” with men you’re interested in meeting. They won’t be turned off by your initiative. If they’re interested, and serious, they will respond. Those are the only men you want to meet anyway, right?

Regarding talking about exes, I personally never speak about mine, and I’ve been married for several years! However, I don’t think there are any firm rules about when to talk or not talk about exes. As you said, we learn something about love from every relationship, and sometimes a person might feel the need to discuss those lessons with their current dating partner. Should that discussion happen on a first or second date? Probably not. Maybe never. Think before you speak!

Much Mazal and blessings for success on JDate!


Rabbi Arnie Singer dated for 15 years before meeting his Bashert. He is currently a dating and relationship coach in Manhattan and the founder of
  1. Dear Rabbi,

    I just ended a relationship with a man I met on Jdate and dated for 20 months. It was a long distance relationship, and we had different backgrounds and experiences. He was formerly in the military, and somewhat observant. He is a retired Conservative rabbi. Although i wasn’t observant, I observed all of his customs at his level of observance, such as keeping kosher and observing Shabbat. We got along great, but we never seemed to move forward. It was a year before I met his daughter, and he didn’t seem to want to include me in many aspects of his life.

    Every year he has large Passover seders in his home, and after dating 18 months, told me he wasn’t comfortable having me come also. I was not invited! I was very hurt, and his only answer was that he wasn’t ready to “present” me to his family and friends. He also continued to log on to Jdate, to just “look” around”, even though I told him it hurt my feelings and felt disrespectful to me. We stopped seeing each other after that, but got back together a month later.

    The last time I saw him I asked him if he thought our relationship had a future. I have reasons to doubt that after all the months of waiting for him to act like we’re a couple, and make room for me in his life. His answer was that he wasn’t optimistic, and he struggles to be hopeful. He said he wanted to continue to be together, and we could “wait and see”. I ended the relationship after that.

    I feel terrible and miss him everyday. My heart isn’t in to the dating scene at all. I understand that not all relationships are meant to be, but I’m confused by the mixed signals he gives me. I talk to other people who tell me that he hasn’t treated me as well as I deserve, and that I should accept that whatever his issues are, they are his issues, and I should move on.

    What do you think?

    Confused in Florida

  2. To Sandra:
    There are no ‘mixed signals’, you were his sex buddy and with all the clues, as not inviting for his ‘large’ Seders’, you should have known you were no more then that. He was a ‘Retired Conservative Rabbi’ Player!

  3. “A few men well above my age range are ‘looking’ at me, I can diplomatically deal with that.”

    You’ve got to be kidding–you’re 58 and reacting to men much older than 68 as if you’re in danger of being stalked. I find so many women’s thinly-veiled complaints about guys paying attention to them to be the zenith of hypocrisy. Most women crave attention, and when you get it from guys who don’t fit your ideal, you kvetch about them. The complaining only makes the complainer look immature and self-centered.

  4. To Sandra,

    I agree with Mike 100%. If he doesn’t show you off to his family you are nothing but a sex buddy! You have got to read the book: “He is just not that into you” All the signs were so clear you would have never missed it if you read the book!! You did the right thing to end it. You always have a right to ask about the future and his answer was so clear – all that was missing was to end it with a big no. He was actually SO clear.

    After reading this book, I know the first date if they are really interested, and then a few weeks later they all say the same thing if they want you. Men say and do the same things when they are interested. If you know it, you are in control… go read that book!

  5. When the soul of a woman overcomes the natural feelings of entitlement, she releases the tension that allows her to be a pure spirit. The paradox is that she will then meet the man of her dreams.

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