You will be more comfortable with your new guy as you begin to know him better. As you do things together, you can find out more about your new beau by asking him questions. The more lighthearted and fun these are, the less likely he is to feel as if he is being interrogated. Asking and answering even seemingly insignificant questions is even more important because it means that you are communicating. If you and your boyfriend decide to be truly honest with each other in these conversations, you can be rewarded with a more successful relationship.
Ask him if his house that contains all his possessions catches fire, and he gets the chance to save one thing after saving his family and friends, what would he save. This question will give you a insight into what he considers to be most valuable. For example, If he decides to choose his phone or laptop, that may tell you that staying connected is important. On the other hand if he chooses something like a family heirloom, then your guy is probably more sentimental.
Ask your new boyfriend to tell you about his most embarrassing moment. You can have a good laugh together at this. This question will reveal how comfortable he is with you. It will also show you whether or not he is able to laugh at himself and find humor in even serious circumstances.
Ask your boyfriend to describe his perfect day. This will give you some ideas as to what activities he finds most enjoyable. You may find out that he is more reclusive if his perfect day involves staying in and watching blockbuster movies while eating pizza. If he lists outdoor activities such as kayaking or running along the beach, it may attest to him being a nature lover as well as an active person.