Dating a man with trust issues is not easy. Trust is the foundation in which two people build a happy relationship, asserts the article, "Why Trust Matters," from TwoOfUs.org, a website of the National Healthy Marriage Resource Center. A relationship without trust is unhealthy and, ultimately, will not succeed. The ability to recognize the underlying source of trust issues can help you and your boyfriend battle mistrust.

Controlling Behavior

A man who has a hard time trusting his partner can come across as controlling. For instance, he may demand all of your free time or discourage you from seeing your friends. A man who exhibits controlling behavior generally does so because he is scared of the vulnerability that is part of loving and trusting his partner, writes psychologist Marie Hartwell-Walker, in “Signs of a Controlling Guy” on the Psych Central website. He may have been hurt in the past and is afraid of getting hurt again or he may have learned the behavior by example. If your boyfriend is exhibiting controlling behavior, but is willing to discuss it and make positive changes, continuing your relationship may be worth it, suggests Hartwell-Walker.

Issues of Insecurity

Your boyfriend may have trust issues due to insecurity. He may not feel like he is good enough for you, may worry that you will leave him for someone else or may unjustly accuse you of cheating. Talking with your boyfriend about his insecurity issues in a sensitive manner may be helpful. You can initiate the conversation by saying, "I really enjoy spending time with you, but I have a few concerns that I'd like to address." Tell him how his insecurities are affecting your relationship and ask how you can help to alleviate his fears. Point out the positive qualities that you admire and appreciate about him. Encourage him to focus on these characteristics, which can help benefit his self-esteem, suggests TwoOfUs.org in the article, “How Insecurities Can Harm Your Relationship.” If there's no reason your boyfriend should question your trust, gently remind him of your faithfulness and your commitment to the relationship. If your boyfriend resolves his insecurity issues, he will better be able to trust you.

Take a Look at Yourself

When dating a man who has a hard time trusting, it's important that you consider your childhood relationship patterns. You may unknowingly be repeating patterns in your romantic relationship that are familiar to you from your childhood. If you felt unloved as a child, you may have unconsciously attracted a man that has trust issues in an effort to make him love you, warns licensed marriage and family therapist Karyl McBride, in "Plant Both Feet in Relationships!" on the "Psychology Today" website. Until you recognize this pattern and make changes, you will likely continue to seek men in which to carry out this familiar pattern.

Important Considerations

When dating a man with trust issues you have to be patient. You may have to offer him reassurance that you love him and that you are there for him. You may have to show more transparency in your relationship than you normally would. For example, you may have to show your boyfriend your call log or tell him who you were talking with. It's also important that your boyfriend work to resolve his trust issues. Signs that he's making an effort might include calmly approaching you with any concerns, not making accusations or making efforts to improve his self-esteem, such as mastering a new hobby. If he isn't willing to work to make changes, consider if your relationship is worth pursuing.