This is an old post but thought I would respond. I am having to matron of honors. One is my best friend since I was 12 and the other is my sister in law. I was maid of honor in both of their weddings. But I really didn't want to choose between them because I love them both. And I really didn't want to pick one or the other. They are going to share the duties. And I am not having any bridesmaids. My fiancee is have two best men also. His best friend and my brother. My brother is actually the way I met my fiancee. And they are actually best friends now. So, I personally think you can have two. Why not? It's your wedding!