I have been in a relationship for a few months and worry about my boyfriend’s attention to his female friend. They have been close for years and have never had any romantic attachments, but he seems to be more comfortable talking to her than to me. I am not jealous, and have not said anything to him about this, but I keep trying to figure out why there are some things he doesn’t discuss with me. I don’t have any problems opening up when he asks about my personal life or my family, but he hesitates a lot and I think it’s because he doesn’t trust me as much as I trust him. How do I bridge this gap? Also, should I worry about his close relationship with this friend of his?
This is a new relationship for you, and building bridges takes time. You may be okay trusting your boyfriend with aspects of your personal life that he still isn’t comfortable talking about. This is a slow process and should be handled with patience because you are both allowed to set your own boundaries. As for his friendship with another person, it predates your relationship with him and his level of comfort with her is to be expected given the circumstances. It’s okay to be jealous of this because that is normal, but it’s also important to be objective about the fact that two adults are allowed to be friends while being in relationships with other people. If this bothers you, talk about it, and let him know how you feel. Not discussing it and assuming your feelings may change with time only leaves room for misinterpretation, which isn’t good for either of you.

A guy I like asked a friend out along with me, and I don’t know if I should agree to go on a date.
Assuming you are all single, and are allowed to date, why not meet him just to get a better sense of what he is like, and what he wants?