Whether you want him to admit his romantic feelings for you or just open up and be a little more honest with you, cracking the emotional walls of a stoic male friend can be difficult. You might even find yourself discouraged by his silence, short responses or his attempts to redirect serious conversation with humor. Several strategies can help you move past his emotional defenses and develop a deeper connection with him.

Begin with Simple Chit-Chat

Sometimes the best way to gain access to his deeper feelings is by starting with an otherwise normal conversation, suggests clinical psychologist Suzanne Lachmann in the "Psychology Today" article "How (and How Not) to Communicate With Stoic Men." For example, if you want him to spill information about his romantic feelings for you, begin a conversation about his past dating life. Ask him simple questions about his past girlfriends or attempts at dating. As his emotions stir concerning these details, he will begin to lower his walls and share some of his feelings with you.

Uncover the Causes

Do a little snooping to uncover the potential causes of his emotional walls. Fear of intimacy might arise from past relationship troubles, paranoia or even depressive symptoms, suggests clinical psychologist Seth Meyers in the "Psychology Today" article "Fear of Intimacy in Men: Cause, Relationship Problems, Tips." Of course, since he's already emotionally distant, you might have trouble getting him to admit the causes of his quietude. If he won't directly open up to you, talk casually to his other close friends, parents or siblings about his past. You might gain some insight.

Open Yourself Up

Perhaps your male friend isn't being open with you because you aren't being open with him. Share your feelings with him. He might follow your example as he realizes you have no fear of sharing your own inner thoughts with him. Share your vulnerability through humor, suggests humorist Robert Wilson in the "Psychology Today" article "The Victory of Vulnerability." A self-deprecating joke here and there will not only make him laugh, but it will also invite his trust. For example, if you are nervous about going to a dance with him, joke about your own abnormal dance moves beforehand. He might open up to you about his own insecurities.

Be Patient

Don't take his emotional wall-building personally, suggests expert on interpersonal relationships Lisa Firestone in "The Huffington Post" article "Five Strategies for Dealing With Your Partner's Fear of Intimacy." Practice compassion and don't grow bitter or depressed over his lack of sharing. Don't place blame on him. Avoid statements like, "You don't even try to be open." Instead, say "I feel like I can't get close to your true feelings." You can gently get your point across without rushing him to open up or laying a guilt trip on him.