Most Helpful Guy
That depends. What caused the two of you to break up? It could be that he realized that he made a mistake when the two of you were together, and wishes things were different. He could have tried several relationships and they failed, and so he is hoping that you will take him back because he wants the comfort of a relationship. There are many different things that could be the reason, but the best way to find out is to just ask him. When he is sending you all of these messages, you need to read what he is saying, but look at the words not spoken. What is he telling you? What point is he getting at? Now, I haven't seen these messages, but based on what you said, this is what I assume the reason behind it is. He is telling you about his life because he wants you to know what he has done, and he wants to open up a conversation about it. If you ask him something about his life, then that allows him to answer it in a way that would help him get to his true purpose. So after you ask him a couple questions, he started asking about you and your life. Then he is asking about your plans after college. He is hinting at your future, because more than likely, he wants to be a part of it. He wants you to ask about his life, so that way maybe you two will build back the connection that you have lost. He is asking about you because he wants you to know that he cares. He will continue asking about you, and eventually it will either end up you guys talking about what went wrong in your relationship, giving each other another chance, or maybe he just wants to see if there is still something there between the two of you. If you want to skip all the random questions, you can just ask him. Ask him why after 5 years he decided to talk to you. It wasn't random, there is a reason for everything. Don't let him talk around the subject. If you want to really know the reason, just ask him and don't let him change the subject.
Most Helpful Girl
Could be that he still has interested in you?