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Dating Advice #50 - High School Hangover

May 8, 2009 | by Rosie Einhorn, L.C.S.W. and Sherry Zimmerman, J.D., M.Sc.

The pickin's are slim enough as it is. And now that someone's finally interesting, her friend is giving her a guilt trip.

Dear Rosie & Sherry,

My friend and I are single Jewish women in our mid-30s living in a Jewish community of about 15,000. Each of us would like to find a Jewish man to date and marry. Unfortunately, we feel like we've already met all the local bachelors!

About two years ago, a single Jewish man in his late 30's moved into my friend's neighborhood, and she has been interested in him ever since. She's told practically everyone but him about her interest. Recently, she briefly introduced the two of us, and he later asked her about me. She told me that it hurt her feelings that he had expressed interest in me rather than her. She asked if I would be interested in dating him, and if she should give him my phone number.

I realized this was uncomfortable for my friend, and told her that I would not date this man if she felt strongly against it. However, she told me that even though she felt hurt, she could not ask me not to date him.

Frankly, the fact that he asked about me got me interested in knowing a little more about him, and I told my friend that she could give him my phone number. At the time, I wasn't sure he would even call me.

As it turned out, he did call and I accepted a date. I also felt I had to tell this to my friend so that she would not be even more hurt by hearing about it independently. Now she claims that this has hurt our friendship!

Now what should I do? I feel like I'm a loser in this either way.


Dear Sandra,

Reading your letter reminded us of a typical TV exchange between high school girlfriends: "You stole my boyfriend and now I'm angry!" Unfortunately, some people enter adulthood with this same mindset toward dating. It's even more unfortunate when people reach their mid-30s without having learned how to date as an adult.

A mature woman understands that she may be attracted to someone who doesn't reciprocate her feelings, and that he may prefer to go out with her friend. A mature woman also understands that the man she secretly pines and has never dated does not "belong" to her. Unfortunately, your friend is not handling this like a mature woman.

We don't want to seem insensitive to your friend's feelings, but she has got to take some responsibility for what goes on in her social life. A woman her age is too old to be interested in someone and do nothing about it. If she was truly interested in her neighbor, she should have asked a mutual friend to intermediate by playing Cupid. "Sarah's such a great person, and I have a feeling that she's interested in dating you. Have you ever considered getting to know her better than as a neighbor?" This approach is less embarrassing than Sarah approaching the man herself, and it also gives him the opportunity to be the pursuer -- a role many men still relish.

Instead of taking action, your friend nursed her secret crush. Then, by telling you that her neighbor was interested in dating you, she put you in the position of either feeling bad about giving up a good opportunity, or feeling bad about hurting her feelings. Each of us is sometimes faced with a choice that will have consequences that make us feel, as you put it, "a loser either way." You tried to be sensitive to your friend, and now it's time to stop beating yourself up about your choice. If your friend can't maturely come to terms with the consequences of what she set in action, well, that's her problem.

You mention the problem of finding guys locally. Frankly, we think that you should move past this incident and focus on your future. If a courtship with this man has developed, you don't need this advice right now. But if it hasn't, we suggest that you start looking for dating prospects outside of your geographic area. Don't wait around for Prince Charming to ride into your community on his white horse. Use Internet dating services. Include dating-related travel in your budget, and consider the possibility that you may have to relocate if you meet someone suitable.

Above all, make the goal of marriage a priority in your life. Approach the search for a future spouse with the same energy and effort you would use to search for a job. Many times, a concerted effort makes the difference between achieving your goals and simply dreaming about them. Good luck.

Rosie & Sherry

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