Nobody knows him better than you so we cannot just make a blank statement and then suggests you. I don't think it would be fair.  Keep in mind, folks who have been in a relationship before usually tend to be more understanding and easy going than the ones who havent been. Also, people do learn from the mistakes in the past and vow not to repeat that again. On the flip side, they can let you go easily as they have been in the similar situation before and you are likely to do something if you have already done it.

   Keeps your heads up and take a right decision!! i know you will coz your smart!!