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DATING MAZE #301: Looking Over the Shoulder
Dating Advice 301

DATING MAZE #301: Looking Over the Shoulder

If I commit to this man, I'm closing the door on all other possible relationships, including my old high school flame.


Dear Rosie & Sherry,

I love reading your dating column and I think you offer great advice. Now that I am finally in a relationship that is going somewhere, I could really use some advice myself.

About three months ago I started dating a wonderful guy. I believe we are compatible in terms of our values, priorities, career goals, and desire to build a Jewish home. At first, I had doubts about whether I was attracted to him, but I have grown to like him, and even to love him. He tells me he loves me and that he thinks we have a future together. All of this makes me very happy.

It also makes me very nervous.

I am having trouble shaking the idea that if I commit to this man, I am closing the door on all possible relationships with other men. For example, I recently reconnected with a male friend who had a crush on me throughout high school -- we even went to the prom together. As a teenager I did not have romantic feelings for him, but as we have grown older I can now see what a wonderful person he is. (In many ways he is very similar to the guy I am currently dating.)

Several months ago I found out that he was engaged, and I felt crushed. But then it turns out he broke off the engagement and is single again. Now that we have reconnected, I can't stop thinking about him. This is obviously a problem, and I feel very guilty about it. If I hadn't been so superficial in high school, I might have ended up marrying this guy, but now I am headed on another path with the guy I am dating.


Am I doomed to always be plagued by these doubts?


Dear Jeannie:

This is an issue that many daters grapple with. We call it "looking over your shoulder," and it means that you hold back from fully investing yourself in a promising relationship because you think that someone "better" might come along. Or you might meet someone who has one or two qualities that the person you're dating seems to be lacking, and you yearn to have that aspect fulfilled.

The reality is that even when you're dating someone with great potential – let’s go so far as to call him your “pre-destined life partner” – there will almost always be someone else out there who appears just as appealing. However, what you may wind up discovering is that the person who seemed so appealing is often less well-suited to you than the one you’ve pushed aside. And if you are fortunate enough for that new man to be a good match for you, he’s not likely to turn out objectively “better” than the person you gave up -- just a different type of "good for me."

We've met many people who’ve spent years looking over their shoulder when they date, often dropping one person to pursue another option that doesn't turn out to be exactly what they'd hoped, and always wondering why none of their developing relationships ever work out. It may take years for them to see the pattern, until they finally realize, "I've been doing this all my life, and now my choices are far more limited."

Long-term Feeling

What is behind this phenomenon?

Often, when someone prematurely leaves a promising courtship, it's because s/he doesn't understand that most enduring relationships develop gradually. You meet a nice guy, and continue to date because you seem to have similar values and goals in life, and find yourself becoming attracted to him, feeling comfortable with him, liking him a lot, and maybe even falling in love. You'll realize that he may not have everything you were looking for, but those qualities become less important to you because he's got other qualities that you treasure and may have never even thought about. If you continue to nurture this relationship, there is a good chance that you'll decide you are right for each other and it will lead to your sharing a very happy life together.

Actually, this seems to be the process you describe with the man you are now dating.

However, if you hold back a little while you are dating someone who seems like he may turn out to be right for you, thinking that there may be a better option out there, or that you might have more of a chance for romance with an old flame who's suddenly become available, you'll never allow that first relationship to realize its potential.

A couple gradually cares about each other and wants to be together.

Some daters hold back from moving a promising relationship forward because they don't feel "fireworks" and are worried their relationship might be missing an important element. Unfortunately, our society has been influenced by romantic scenes from movies and books, and we think that this is what a "right" relationship is supposed to feel like. It's not true. Sometimes it does occur, but more often what happens is that a couple gradually comes to care about each other and wants to be together. And what matters most, and what makes a relationship turn into a long-term, happy marriage, isn't what two people feel when they first meet – it's how they feel when they realize they are right for each other, and how they carry that feeling forward over a lifetime.

Another reason a dater may start to think that someone else might be better is because she's afraid of where her current relationship is going. You've told us that you're "nervous" and happy at the same time. This is normal. It can be a bit scary to think that you may be moving toward making a lifetime commitment. It's a big step. One thing that can help you get a better handle on this is to spend some private time writing down your feelings.

Draw three columns on a piece of paper, and list everything you're nervous about in one column (such as, "I'm too young to get married" or "What do I know about being a wife?”). In the second column, describe the worst thing that can happen about that item. Think about how you could answer or deal with each "worst case scenario" and list your solutions in the third column. Put the list away, and look at it a few days later. Do you still feel the same way about these issues? Are you calmer about any of them? Do any of them seem like they're really anxiety about the unknown more than anything else? Is there anything that seems like a genuine issue that you can't resolve easily? Is this something you can address on your own, or would it be better for you to talk about it with either a third party or the person you are dating?

We think that once you understand why you're nervous, and that there are ways for you to deal with these issues, you'll feel calmer. And you may decide that one of the reasons why you seem interested in your high school friend is that it is safer to think about him than to deal with the process of a serious relationship that is moving forward.

High School Closure

Let's talk a little more about that guy from high school. When you're nervous, it's much easier to think about an old flame through nostalgia-colored glasses than to focus on your current, developing relationship. It seems to us that this is what you are doing. You imagine that you might have ended up with this boy if you had felt the same way about him that he did about you, but that's just fantasizing. You're both very different than you were in high school – your values and what you're looking for in life have changed, and you are a much deeper person than you were as an adolescent. The boy who once had a crush on you may have turned out to be a very fine man, but that does not necessarily mean that if you got together you'd be able to develop the same kind of connection you already have with the man you are now dating.

Stop being so hard on yourself for having been a normal teenage girl.

It seems to us that you need to give yourself closure about your high school friend. One way could be to stop being so hard on yourself for having been a normal teenage girl who didn't feel the same way about someone who had a crush on her. He's someone who was interested in you years ago, before you were ready to be serious about anyone, and now you are dating someone who may be right for you. The two have nothing to do with each other.

And as with any friendship which is getting in the way of your potential “marriage relationship” moving forward, if the high school guy is sapping your emotional attention, we highly recommend that you cease any contact with him.

We hope that after considering our suggestions, you will allow yourself to focus on the man you are dating, to see if things blossom into a relationship that is truly right for you.

Rosie & Sherry

January 30, 2010

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Visitor Comments: 12

(12) rose, June 15, 2010 3:44 PM

if you are still young, go out with this other man as a friend and see where it goes. you may end up with neither, but will still have time to learn from this and look for another. it may be a case of the grass is greener on the other side!

(11) David, April 26, 2010 11:37 PM


Good riddance anon. Don't let the door hit you on the way out.

(10) pedro, April 18, 2010 12:27 AM

Love Equals Fire

If you do not know if you love one person then you don't. Love is hot like fire and as soon as you put your hands in the fire you immediately know your are getting burned. Same with love, leave these two guys. I hope you do, for their own good.

(9) anonymous, April 12, 2010 6:45 AM

make a list of priorities and stick with it

Make a list of priorities and then stick with it. I am a young woman in her mid twenties who holds a high level of education, wears a size four, comes from a wealthy family, and have a reputation for doing community service in my community. When I was secular, I was beating men off with a stick. Now that I am religious, FORGET it! People in religious communities have unbelievably high and unreasonable standards for dating! The men want a super model who dresses tznius, is a genius who is willing to use her education to cook and clean, etc. At this point, I am DONE with Jewish men and their ridiculous standards and am looking for a non-Jew who is willing to convert :-)

(8) Rachel, February 22, 2010 10:48 PM

Happens a lot...which is the problem

I know a lot of people who think like this all the time. Always wondering if the perfect person is just around the corner. Of course, these people are very single and many over the age of 40. Don't spend the next decades looking for an ideal that isn't a real person!

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