Hello Heather, I apologize I had not seen your response. After reading over your response, it seems to me that your husband had a lot of people involved in his life before he met you and now you are feeling like a puzzle piece looking for your place to fit in. He may even have some habits, that may have been ok in his old life, that you are just not comfortable with and you have to let him know that. You can tell him something like 'I know that ____ is your friend, but I am a private person when it comes to our business and it makes me feel violated when you tell him our personal business.'
Your husband seems almost like he wants to get a reaction out of you or he wants to see how you will react to something, maybe you are not being clear to him about the things that are bothering you. If something bothers you, you have to spell it out plain as day so that there is no misunderstanding about it, and if he doesn't want to change then the two of you will have to come to some type of compromise. If he won't compromise, then there is a real problem.
No adult should feel the need to be entertained all the time, however, the two of you should do some things together and spending quality time together for the good of your marriage. It's understandable that you are guarded as long as you don't blame your husband for your ex's mistakes.
I welcome your thoughts, let me know if you want to talk more