click here to jump to start of article
Join Our Newsletter

Get latest articles and videos with Jewish inspiration and insights​

Dating Maze #258 -  Almost the One
Dating Advice 258

Dating Maze #258 - Almost the One

While all her friends and relatives are married with kids, she's still searching.


Dear Rosie & Sherry,

I am an "almost-40-year-old" single female. I have gone on a lot of dates, but it never worked out at the end -- sometimes they were not interested in me, and sometimes vice versa.

All my female relatives, friends and co-workers are married with kids. I cannot attend family parties anymore because of the way these married people all ask me: "Why are you not married already? What are you waiting for!" So you can imagine the pain and heartache that I go through every day.

I recently met a very nice guy. We emailed a few times, talked on the phone a few times, and eventually met in person. We had great time together. The attraction and chemistry was very obvious. He was exactly the guy I was looking for. He called the same night and also next day to plan for a second date. But he did not follow through and I did not hear anything from him again. I was extremely upset about this and cried for almost two weeks.

My question is not: Why he did not call, or like me enough?, because I understand that people are complicated and have their own reasons which I might not understand. But my real question is: Why do I have to go through this pain right now? Is it not enough that I am almost 40 and have already gone through so much in terms of dating and heartbreak? Surely I have learned enough over the years about humility and understanding.

Can you help me understand why I have to endure such a difficult challenge?


Dear Beth,

To finally meet someone who has so much potential, and get disappointed as you were, must have been excruciating.

We know that the pain isn't lessened that much by the realization that this man seems to have a lot of fears that he hasn't been able to deal with. In other words, it doesn't matter that he, rather than you, has the problem. The fact is that you were finally excited about someone, got your hopes up, and were crushed when it didn't materialize.

But yes, there is something positive that comes out of this. We call this "meeting someone who is almost-the-one." It gives you encouragement that, after all of those dates with people who were totally wrong for you, you finally met someone who was very close to being right. That can give you hope that there is someone right for you, and that you may be close to meeting him.

This idea has enabled a number of people to not only look at dating more positively, but the right attitude to actually find the right person to marry within the year. There are some excellent, inspiring articles on of women sharing such experiences:

Private Talk

For now, we have two suggestions for you. The first is to keep going to events, networking, etc. We've seen a mushrooming of weddings among people in their mid- to late-30s and early 40s. We don't know why these marriages are happening so much later than the couple would have wanted, but they are all thrilled to have met the right person.

The next is to muster the courage to have a diplomatic talk with your relatives, friends, co-workers, etc. They have no idea how hurt you are by their comments, and yet they seem to want the best for you. You can approach each person in a non-confrontational way, perhaps asking to meet her for coffee. Consider saying something like:

You don't understand how difficult it is for me.

"I know that you love me and want the best for me. But I don't think you understand how difficult it is for me to see you with your family and to hear you give me well-meaning encouragement to get married. I really do want to get married and I wish I could have the wonderful relationship you have with your husband and children. I'm trying very hard, but it hurts when you ask me why I'm not married and what I'm waiting for. Even though I love getting together with you and my other friends, it is so painful for me, and I feel worse whenever someone asks me these questions."

If you impress how much you know the other person cares about you, and calmly explain how this affects you, you'll get your point across and may be able to find a better way of relating to each other in the future.

This can also provide a good opportunity for you to enlist the other person's help. You can say:

"I know you want to help me, and I have a suggestion about how you can do it. Please keep your eyes open for someone who might me right for me. Ask your own friends and co-workers if they have any ideas. I am looking for someone who is (list three personal qualities that you would like to see in your future spouse). You can tell him this about me: (list three personal qualities that make you a unique individual). I'm willing to listen to all suggestions that are in the ballpark, so please call me. I'd appreciate this so much."

We don't know why some people have to wait so long to find the right person, and others get there with seemingly little effort. But we hope that for you, good news is right around the corner.

Rosie & Sherry

June 6, 2008

Submit Your Dating Advice Question (Click here)

Give Tzedakah! Help create inspiring
articles, videos and blogs featuring timeless Jewish wisdom.
The opinions expressed in the comment section are the personal views of the commenters. Comments are moderated, so please keep it civil.

Visitor Comments: 16

(16) Goldie, July 22, 2008 7:53 PM

Nothing ventured, nothing gained.

I agree that you should contact the guy again, at least one more time. His failure to call you again after two good contacts could be due to extenuating circumstances. In life, things happen over which we have no control. Maybe he got cold feet, maybe he thinks he's not good enough for you, maybe his parakeet died! Don't always blame yourself for the failure of another person to follow up on what at first appears to be something promising. You only go around once, so don't let opportunity slip away. As the old saying goes, he who hesitates is lost. Good luck!

(15) Susan, July 14, 2008 10:33 AM

He Did Follow Through.

Beth, He called you twice. Twice!! What happened on that second pnone call to change his mind.

You stated he called you that evening and again the next day but didn't follow through. Follow through with what?
What plans did you make and where did you plan to go on your second date?

Why didn't that happen? Did he simply not show up?

(14) Anonymous, June 23, 2008 7:52 AM

Sisi that is a great comment

comment # 3 by sisi
Thank you - your comment made me feel much positive about my "situation"! :)

(13) Anonymous, June 15, 2008 10:08 PM

I agree with Sisi's comment

I agree with Sisi, let's go Kadima with G-d's help!

Email him or call him don't worry about the rules let's say a quick tefilla and give it a go!

Good Luck and let us all know what happens. I am davening for you!

(12) Daniela, June 15, 2008 10:10 AM

unsolicited advice

Unfortunately, saying " I really do want to get married and I wish I could have the wonderful relationship you have with your husband and children. I'm trying very hard, but it hurts when you ask me why I'm not married..." leads to unsolicited advice, as it's taken as a request rather than a statement, ie, "what am I supposed to do ?" The fact of the matter is, sometimes people just have to be put in their place. Admittedly we have to acknowledge that they care and want what *they* think is best for us, but in the end we also have to admit to ourselves that often they have their own need meddle at heart even more.

See All Comments

Submit Your Comment:

  • Display my name?

  • Your email address is kept private. Our editor needs it in case we have a question about your comment.

  • * required field 2000
Submit Comment