click here to jump to start of article
Join Our Newsletter

Get latest articles and videos with Jewish inspiration and insights​

Dating Advice #102 - Too Many Choices
Dating Advice 102

Dating Advice #102 - Too Many Choices

When it rains, it pours. He's got 3 women lined up ready to get married. Which one should he choose?


Dear Rosie & Sherry,

I'm no Sean Connery (Jewish version, of course) and have as many faults as most, but I'm facing an "embarrassment of riches" that's got me off-balance and confused about how to proceed. I've met three women, any one of whom by any objective measure would make a superb long-term partner or wife.

All three dates started off without any indication of a long-term future. Lately, however, I see clear signals that each of these wonderful women is moving toward commitment. I have no problem moving in the same direction, but of course I can't "juggle" three different people all with burgeoning emotional attachments.

I'm not worried about who should be my "first choice." That decision hasn't been made yet, but I can deal with the question and arrive at a confident answer. My problem is I think time will tell who is my favorite... and meanwhile I'm playing with their emotions and, in a sense, misleading them. I feel guilty, ill at ease, duplicitous, and cheap.

Thanks for listening. I look forward to your sage advice.


Dear Wayne,

Your predicament is precisely the reason why we recommend not dating more than one person at the same time. Since you've already described all of the difficulties that multiple-dating creates, we don't have to list them for you. But we do have one observation that might not have occurred to you: It may not matter which of the women you ultimately choose. It sounds to us as if you could have a happy marriage with any of them.

We've always believed that most people are capable of building and maintaining a satisfying and enduring marriage with any one of several different people. Each possibility requires the basic ingredients (common values and goals, physical attraction, admiration, respect, affection and emotional intimacy), but from that point onward the couple needs to use their personal efforts and skills to enhance their bond.

If each potential couple were to use their efforts and skills, and make the success of their marriage a priority, it would be hard to characterize any one courtship as being "better than the other." Each will have different good points, and each will be mutually satisfying in its own way. We like to point this out to "serial daters" who can never make a choice because they always think someone better is around the corner.

We also like to point this out to people who keep rejecting excellent (but less-than-perfect) suitors, on the grounds that "they are not my soul mate." While Jewish tradition does speak about a soul mate, we can never know for sure that we've found our "beshert." And that's why picking a spouse comes down to using your good sense and intuition to pick the one who is best for you.

Some courtships might be "smoother" with less challenges, and others will have more friction. (We like to call it "creative tension.") But neither arrangement is inherently better than the other. Sure, the smoother courtship is easier, and of course you don't want to get into any situation that is too emotionally taxing or unhealthy. But... the personal growth -- and growth together as a couple -- can be much greater and ultimately more rewarding when there are certain challenges to overcome.

This is the reason that many widowed veterans of long-term, happy marriages have successful second marriages. They understand that the second time around will be different than the first, but will be a mutually-rewarding experience just the same.

It sounds as though you are optimistic about what the future might be like with any of these three women. You also seem to realize that intensifying three separate courtships will be extremely complicated, as well as unfair to each of the women. It's possible that by juggling three at once, you'll actually find it harder to choose between them because you won't be able to devote enough emotional energy into developing any one of the courtships.

It's also possible that 3-timing these women may end up backfiring. If they find out about each other, you could end up with three failures and a bad name in the dating world.

So why have you continued to see all three of them? Probably because you enjoy all the attention! But now it's time to just "deal with the question and arrive at a confident answer." We're sure you'll make the right choice. Good luck.

Rosie & Sherry

January 19, 2003

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: 2

(2) Anonymous, July 12, 2002 12:00 AM

from crocodile tears to a crocodile smile.

The word integrity applied to many territories of life such as business, moral, social, our self and also to friendship. Majority of peoples have the basic people’s skill to know if you want “All three relationships started off just "friendships," without any suggestion there would be a long-term future.” if you have indicated “just friends” I am sure they are able to respect your wishes, as friends usually do.

You are the only one who is responsible to where are you going. And in my view “I feel guilty” with “I'm not worried about who should be my "first choice."” Make your crocodile tears to a crocodile smile.

I am sorry Sherry and Rosie but a spade is spade, and for my bad English too.

(1) , July 7, 2002 12:00 AM

about time

The truth is that I think it is great that you are reaching out for help and not just following along. You notably did not try to get yourself in to this situation, but now that it has happened, it seems like it might be time to be straight with them. Of course after deciding who to continue with, to explain to the other women that you are NOT rejecting them, but that you have come to realize that you feel attatched to someone else, and don't want to lead them on. I think that in the long term you (plural) will all appreciate your honesty. Good luck!

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