Model Openness and Relationship Security
To help your boyfriend learn to trust you, demonstrate your own willingness to be open while creating a judgment-free zone. Of course, someone has to go first. If he is afraid to be vulnerable, help him feel at ease by showing your own vulnerability first. Tell your date if you are nervous, shy or uncomfortable. Encourage him to express his feelings, and accept them without judging them. If something goes wrong on a date, accept it and move on rather than harping on it. Show your date through your actions and words that you are accepting and kind.