Firstly I want to tell you that I certainly understand that the shidduch parsha is quite a difficult one and a serious one. It is not as fun as kids think it is going to be. If you are lucky to hit it on the first shot, meaning if Hashem truly blessed you and sent both of you your basherts right out of the gate, you truly would have been the luckiest people, because it would save you from the heartache of dating.
I know people laugh and make fun saying “don’t marry the first girl, or the first boy, you wont have anyone to compare them to. The thing is why do you need to compare? You have to judge each shidduch on its own merits and not be looking over your shoulder or around the corner for what else is out there. Comparing is a waste of time because it never stops. You just have to work with what Hashem sends you and see if this shidduch will be a good companion for you, a good parent to your children, a good spouse, a good partner, a good role model. Is there a physical attraction? Is there an intellectual connection? That will lead and build to an emotional connection.
Having said that the question I would ask you is this, what could you have done differently at that time to bring about a different outcome? Did you show the real you? Did you act appropriately? Did you do anything you shouldn’t have? If there is something you could have or should have done differently that would have kept the process going, then having realized that it would be worth pursuing. Humbling yourself by contacting the shadchan recognizing that you made a mistake and you might have given her a wrong impression of you, or you might have unintentionally offended her or turned her off, and that you would be honored if she gave you a second chance, might portray you in a new light as far as she is concerned.
However, if there is nothing you would have or could have done differently back then, and there is nothing about you that you know for fact that was in your control that caused the break up then you have to consider the fact that maybe it just wasn’t bashert. Understand that you can’t change other people and you shouldn’t change yourself to please other people because you will never be happy and it won’t work out in the end. Many people in such a situation think “I can change to please her, I can be who she wants me to be” and that doesn’t work. So I am hoping that is not the case with you. If she is looking for something that is not in your make-up or not in your skill level, or not in your personality then let it go.
However, as I said, if there is something worth pursuing because you think it was a misunderstanding and you can actually easily be on the same page go back to the same shadchan and be honest and straight-forward; brace yourself for rejection because it could happen but its worth it if on the other hand you succeed.
It is absolutely true what people have said about the second time around and how happy they are, but it is also true that the divorce rate has risen tremendously among young couples. The commitment to hang in there and keep making it work is just not there. Young adults going into marriage for the wrong reasons, choosing their spouses on the wrong criteria, thinking that they can change each other to bend to their own requirements is just leading to heartbreak, dysfunctional and broken families and children who are lost and in tremendous pain. So I say this with the utmost and sincerest blessing for your success and happiness.
If you have the confidence that there is something worth pursuing by all means go for it!