Dear Rabbi,

I have known this man for years and he has always liked me. However, I’m not attracted to him. My problem is that I know if I was to give him a chance, he would treat me right. He would take care of me.

I have gone through many relationships where I was treated badly. I truly wish I could find someone who will treat me right. Now that I’ve found him, I’m just not into him.

The problem is he can’t completely keep up with me intellectually. When I speak of literature, history, or even politics, he has a blank look on his face. Still, I am attracted to his personality. It’s his looks mainly that I have a hard time with. I know that it’s shallow and superficial, but it’s how I feel.

I’m caught between being treated like I know I deserve and having physical attraction. I do love his big heart and his personality in general. I do want to give him a chance. But if it doesn’t work out, I don’t want to hurt him because he is a dear friend. I also don’t want to miss this chance if he could be the one I need.

Please help me. I don’t know what to do.




Dear Caught-in-the-Middle

Attraction is a requirement in any romantic relationship. The level of that attraction is a matter of personal preference. I’ve seen attraction sprout in the most unlikely situations. In your case, since you’ve known this man for many years and are very close with him, I’m guessing that if attraction was going to appear, it would have done so already.

But relationships are very personal matters that grow out of personal decisions. The person you find attractive is not always a good relationship partner. So when entering into a relationship, you need to analyze and weigh many factors before deciding whether to enter into it or not. Under certain circumstances a person might enter into a relationship that in different circumstances they would not have. A 25-year-old woman will base her decision on different factors than a 45-year-old woman.

If having the loving companionship of a man you care for is more important for you at your stage of life than your level of attraction to him, then you should base your decision on that. If you’re willing to roll the dice and continue your search, then you should be guided by that. Decide what your priorities are in a relationship and follow them… as well as your heart.

If you decide to try and make a relationship work with this man, then go all out and do your best.  If it doesn’t end up working out, you won’t have anything to feel guilty about. You might end up losing him as a friend if things don’t work out, but that’s the price you pay for the chance to find love. Better to have loved and lost…

If you’re not prepared to put in the effort to really make the relationship work, then you probably should remain great friends and find a man you are ready to love.

With Blessings,


Rabbi Arnie Singer offers dating and relationship advice on both of his sites: and He is the author of From I to I Do: How to Meet, Date and Marry Your Mr. Right.
  1. Dear Arnie,
    Thank you for your sincere answer to a question that many of us have.

  2. So good to get a chance to ask this question. Thank you.
    I was married to a man 19 years younger than I am. At 67 the people I hang around with doing poetry readings and discussing art are in their 30’s. When I go out to dance, I dance. I dance every dance the whole night by myself because I love to dance.

    Men my age are interested in things that do not attract me at all. I don’t play games, cards, tennis. I don’t drink. I don’t like small talk but want to get right into the conversation about mind, spirit and enlightened choices.

    My older friends say I am too intense. Men in their 40’s have asked me out but I have anxiety around being “inappropriate” and a deep desire for a lasting relationship.

    The resultant mental drama is something I do not want in my life. I am not casual about anything in my life particularly about dating.

    I have my filter set for 50 to 65 in searches but younger men keep reaching out for me.

    I shudder when I think of playing cribbage on an over stuffed couch watching reality TV sitting between two dogs. Believe me, that scenario is what keeps appearing when I look in my age range.

    Enlighten me. Lift me up.


  3. What a wishy-washy non-response from the rabbi– pure doublespeak. He opens with a clear, unambiguous statement– “Attraction is a requirement in any romantic relationship”– then goes on to say the opposite: “If having the loving companionship of a man you care for is more important for you at your stage of life… then you should base your decision on that.” Well, which is it? Or is doublespeak the goal? Imagine asking this rabbi for driving directions. “You have to go east to get to NY. But if at this point going west is important, then you should base your decision on that.” Priceless. To add to the irony, the letter writer has signed her letter, “Caught-in-the-Middle.”

  4. This is to Cherie,
    Good for you, girl. Enjoy you life and don’t care about what people say. I’ll be on the same road soon after my divorce from a 2nd husband with NPD is trough. I am 33 on each side LOL and am also asked out by younger man but do not want to date until am divorced.

  5. Dear Caught,
    You make me laugh. Devotion is a two way street. This guy must have OCD for you. I’d be careful and quit string him along.

  6. A more interesting, relevant, (meaning happens pretty often)l topic would be
    “He’s sweet, but he doesn’t make enough money. What should I do?”
    Your topic is often an excuse for the real topic I have just described.

  7. To answer Caught-in-the-Middle’s dilemma: If you can see yourself waking up next to this man every day for the rest of your life than this relationship deserves a chance. If your answer is “no” than obviously you can only remain friends.

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