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Hi Whit,
It sounds like you’ve got a real dilemma here. I know what it’s like to be in a complex situation, but I can only imagine what it’s like to add a child on top of it all. Trust issues are no fun. Over-thinking is no fun either. It may be best to think of why you’re feeling the way that you are, before focusing so much energy on covering up your insecurities.
Matt is right, you feel this way for a reason. Nobody is born with trust issues. You’re taught to feel the way that you do over time and through your experiences. Don’t discount your emotions and your gut-reaction when it comes to your relationship! Your concerns are just as valid.
Communication is always the key to finding harmony in a relationship. It sounds like you do voice your concerns, but try a different method. Try and get on the same page emotionally. Open up to him and let him know how vulnerable you are. Don’t accuse him of anything, but admit your insecurities and ask for his help. Chances are he will want to change his habits and will make a stronger effort for you. Whether it’s making an effort to introduce you to these friends of his, or whether he stops communicating with them out of respect for your feelings, there are steps he can take that are reasonable for you to ask for.
Your boyfriend is allowed to have friends, but you don’t have to mask your insecurities about them. Successful relationships are about being on the same page, and trust is built through communication.
Hang in there and I hope things improve!
Mike