Am I overreacting or do I have a right to feel hurt?

It is a little insensitive of him. But I think he sounds a little immature and is trying to make you jealous to make himself feel better. How would he like it if you told him you fantasize about having with Antonio Banderas, but probably wouldn't in real life... even though he's totally hot and gorgeous and amazing and your dream man. He'd be jealous. Your mistake was telling him your insecure. Who wants that?! People want others to be confident. Even if you're not you need to fake it! Stop telling him your innermost thoughts and fears and insecurities... sounds like he uses them to get a reaction out of you to reure himself. Just act confident. Get out there and have a life of your own. Don't tell him everything. Let him think he has something amazing in you!!! You have to work on believing that about yourself or you're going to attract jerks who are insecure and stay with you because they have issues. Is that really what you want?