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Dating Advice #44 - Ready to Give Up
Dating Advice 44

Dating Advice #44 - Ready to Give Up

After so many rejections, he's basically given up hope of finding his match. Is there any way out of this rut?


Dear Rosie & Sherry,

I'm a single, non-religious Jewish male age 41, and have never been married or even engaged. While I'll date non-Jews, I prefer Jewish women since that gives us something in common. However, when I date, women give me the usual "You're a very nice person, and I'm sure that you'll eventually find someone, but that's not me."

In my younger years I was incredibly shy and did not date at all. Now, I would like to find Ms. Right to settle down and get married. I go on many blind dates. But it never fails, only the girls I don't find attractive tend to be interested in me.

I don't think I'm superficial, because there have been many women who I was attracted to who were, for example, overweight. I like girls with nice, fun personalities. I don't come on very strong, so I am sure I don't actually scare them away.

After a lifetime of this, I've pretty well given up on the idea of dating, let alone marriage. I work full time, love books & movies, art museums, and learning -- yet women call me dull and uninteresting.

So the question is: Is there something wrong with me that I get attracted to women who don't want me? Or is this normal behavior? All of my friends seem to be happily married except me. Please give me some advice to get out of this vicious cycle.


Dear Mike,

You've hit a disheartened stage that many older singles get to after years of unproductive dating. We're here to tell you not to give up hope. We've seen many people in your situation find a person to happily share their life with. The fact that so many women let you down by saying you're a nice person actually says a lot. Men who aren't good marriage material don't hear this from their dates.

One of the problems older singles face is that without intending to, they become very wrapped up in themselves, and that makes it harder for them to get married. This is a natural phenomenon -- you are the center of your life simply because you haven't had an opportunity to share it with anyone. You've built a lifestyle that includes a job, financial independence, a comfortable apartment or house and a group of friends, and have developed interests that you can enjoy on your own.

So in order to experience dating that leads to marriage, long-time singles have to re-learn the art of trusting another person with intimate information, sharing the center of their lives with someone else, negotiating and compromising, and looking more optimistically toward the future. One book that can help you in this area is "The Inner Circle - Seven Gates to Marriage" by Shaya Ostrov (Feldheim Publishers).

You face another challenge that has kept you from getting to marriage. You tell us people consider you dull and uninteresting. This may be because you are introverted and have a hard time opening up to someone else. Or it may be because most of your recreational pursuits are solitary in nature.

You can't change your personality type, but you can develop some skills that will help you be a more interesting on dates. See if you can branch one of your interests into something that's more interactive -- like joining a filmmaking workshop or book review club, for example.

If you have trouble sustaining interesting conversations, enlist a friend or two to help you role-play dating conversations. It may take several sessions, and your friend must be willing to offer constructive criticism, but it will pay off as you strengthen your conversational skills.

We also suggest that you try to vary the things you do on dates -- like a museum, miniature golf, etc. Interactive activities take the focus off of trying to "make" conversation and at the same time your environment and activity gives you lots of material for talk.

Our final advice is to get yourself a dating advisor. We find that men and women in their 30s and 40s achieve maximum dating success when they have the one-on-one help of a married friend or mentor to give them support and guidance when it comes to dating.

A dating advisor doesn't necessarily need any special training, but people who are interested in assuming these roles can participate in seminars offered by "Sasson V'Simcha" or the "Seven Gates Institute."

We hope that you don't give up on the hope that you can find a great spouse. Take a month or two off from dating if you need to recharge your batteries, but by all means give yourself a new chance at dating success. With the right effort, you'll be able to date successfully and will be appealing to great marriage-minded women. Good luck.

Rosie & Sherry

December 16, 2002

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Visitor Comments: 19

(17) kaela, July 2, 2013 5:30 AM

does this make me crazy

I'm considering giving up dating at age 20 it's to much heartbreak and dealing with boys not men for me to Deal with

(16) Jason Alatorre, December 3, 2011 9:00 AM

I am in the same situation,but different

I hit that rut as well so hard that it is impossible to find anyone. not even the women I find non attractive won't even date me. I come off as strong yet careing person. Is it just me or is women who have found the right guy are soo scared that they break up with them?

(15) Avis, February 26, 2011 12:26 AM

Want to correspond with him

Hi Rosie and Sherry. I liked what this man wrote. He shares similar interests with me. I'd like to just talk with him, email him, even if it just doesn't go any farther. At least we could share. Thanks for your inspiring site. Avis

(14) Anonymous, October 22, 2010 1:44 AM

Wow - I wish I could meet a dull uninteresting guy.

Usually people who come across as interesting are putting on a show. I don't date. As a rule. False personas always crack open to reveal a more disturbing truth. Besides, I'm incredibly dull and uninteresting. I love reading. I live in museums. I wish I could meet a guy who could be completely happy just being quiet with me. Dating is for gamers. Hopefully those of us who just want to be ourselves can find happiness in this world.

(13) heather, June 12, 2010 8:01 AM

give up on dating...and enjoy your life

I grew up in a half-Catholic, half-Jewish home in Los Angeles. I am 42 years-old, and had completely given up on dating a little more than 10 years ago. I am still happy working on my career, and in the rare time, with friends. Don't worry about it. I think that in these modern times, the idea of marriage (at least in a "traditional" sense is dead). There are far more important things to deal with in this age. What is happening in the Gulf, for instance? I can't think of anything more important that that, although I work with inner-city children every day, and in a hospital at night. My God, who is selfish enough to worry about anything else nowadays?! Why on earth would you be worrying about a mate? Please explain. I cannot understand. -heather

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