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Dating Advice #246 - Perfect on Paper
Dating Advice 246

Dating Advice #246 - Perfect on Paper

Her family thinks she's crazy for not grabbing this guy.


Dear Rosie and Sherry,

About 5 months ago, I broke up with a guy who I went out with for about six months. We were about to get engaged, but it didn't work out in the end. The guy was, generous, caring, and there was nothing I disliked about him. But still throughout the whole courtship I was full of doubt, and honestly, I was relieved when it was over. I got over it really quickly and hardly missed him.

Now, a few months later, he has contacted me to start dating again. My family and friends are all pushing me to go out again because he was such a great guy and fit into my family really well. I am scared that maybe he is my soul-mate and if I don't go out with him, I'll have missed my big chance. I don't know and the doubt is killing me.

I would really appreciate your advice on what to do.


Dear Denise,

Feeling relief when a relationship is over is usually a sign that it wasn't the right one.

Sometimes, a person seems right for us in many ways. We call it "being right on paper." He's got many of the qualities we are looking for, we can appreciate that he is a good person, and we think he will make a good marriage partner. But something isn't quite right for us. Maybe we don't feel a strong emotional connection, maybe we are uncomfortable about something in his personality that won't bother the next person but isn't a good fit for us, maybe we just don't like him enough. Yet, because of all of this person's positive attributes, we invest a lot of time and energy into making it work.

We continue to date, hoping that with time things will get better. But it doesn't happen. We feel guilty about ending it, thinking perhaps there is something else we can do, and wondering why we aren't excited about something that should be right for us. And when it finally ends, we either feel confused as to why it didn't work out, guilty about hurting someone we didn't intend to hurt, relieved that it is finally over, or a combination of these emotions.

We can understand your family's interest in re-opening the possibility that this will work out, but you have to be honest with yourself. If you were to go out with him again and nothing about him or about your life has significantly changed, you're asking for more frustration.

What could make it worthwhile to start dating him again? Only in the event there was an issue that was a major sticking point between you, and it has been resolved. For example, if he smoked, and smoking was a deal-breaker for you, and he worked hard to quit the habit. Or if he didn't have a lot of ambition, and has now embarked upon a path in a determined manner. In such a case, you could consider dating him again.

Or, perhaps your perspective has changed. You may have come to realize that you didn't need the fireworks you thought you had to feel, or that the reasons you broke up don't matter to you any more, or that you were going through a stressful time and didn't allow yourself to open up and you are ready to do so now, or that you really do like him. Then, it would be worthwhile to date him again. We've seen a number of couples succeed the second time around when whatever stood in their way the first time is no longer a barrier.

From your letter, we don't see any of that. You say that you're reconsidering dating him because your family is pressuring you, and because you are afraid you are passing up the right person for the wrong reasons. But you're not telling us that you miss him, that you decided you really do care for him, that what bothered you the first time is no longer relevant, and that you are hopeful about the prospect of trying to resurrect this relationship. Don't give into the pressure. Because they don't have to spend the rest of their lives with him. But you do.

Rosie & Sherry

December 15, 2007

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Visitor Comments: 6

(6) Btoche, December 9, 2011 12:09 AM

wrong answer

i think for rosie and sherry the easiest answer is always to cutting off the dating; requires less responsibility and what most would like to hear. isn't love a decision?? why not instead suggest to decide and commit to care about him and love him before going out again and see if deeper emotions grew to be willing to commit to a lifetime relationship?? (i think most girls hope there should be something which they can't describe and that's why they aren't willing to give it fair chance with commitment so long as their imaginary thing isn't there) we believe outside evokes inside feeling; so why not ask if they are religious and shome negia, so they are missing an essential emotional generator between man/women; so as her to lower her current expectations??

(5) Marcy, January 2, 2008 3:46 PM

i've been there-feel with you.

Thanks Rosie and Sherry for bringing these points to ponder. I feel that singles (i'm single myself)have a difficult ending a relationship that they've been in for some time. If he's right why don't we feel anything? and if he's not right why the dating for so long? just penning my thoughts to paper.
I really feel for you Denise and wishing you the best of luck in finding the right one!


(4) Yehudis, December 31, 2007 4:25 PM

how can you know?

Maybe, rather than it being a sign that he is not right for her, it is a sign that she is not interested in marriage. Without knowing more about her, her age, how many men she has met, and her dating history, how can you know?

(3) Anonymous, December 18, 2007 3:03 AM

I've been there too- and he WAS right for me

I too went out with someone and had so many doubts- of course it was a relief when it was over! But a while later I decided to try again and to give it my all this time! we are now married for almost a year and I can't understand how I didn't see him that first time around the way I do now!

(2) Anonymous, December 16, 2007 8:26 AM

I've been there- he's not right for you

I was in the same position and it means he is not right for you. In grad school I dated a wonderful man for several years. He was everything I wanted "on paper" but we never really clicked. We kept trying to make it work because we should have been so good together. Eventually I realized I kept hoping he'd find someone else and break up with me, and that's no way to live. So we broke up and I was relieved, and just hoping he'd find the right person he deserved.

During that relationship I asked all my married friends or family members "how do you know if it's right?" And they all said that you just know. Well, I knew... but I knew he wasn't right and wasted a lot of time not listening to myself.

I'm now married to a wonderful man, and the advice was right, you just "know." So listen to your gut, if it's telling you that he's not it, then he's not it and the right person for you is still out there waiting.

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