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