1. Develop a trusting relationship. Make him feel special by showing an interest in him as a person. Ask him about his passions and his dreams for the future. Stay positive and open to the things that he is telling you to make him feel comfortable. Tell him vulnerable things about yourself that will make him feel special that you trust him with knowing meaningful things about you.
Tell him what your greatest fears are or share one of your most embarrassing moments.
If you show you trust him, he will feel more at ease and open with you.
2. Listen to him and avoid judgment. Allow him to show you who he really is. Let him know he is free from judgment and that you appreciate the things that are unique about him. The goal is to develop trust between you and him that lets him know that he can speak freely to you about anything. A guy can get reluctant to share intimate feelings. The fact that you could reject him may be what's holding him back. Let him know that you will not criticize him or reject his feelings regarding personal issues.
Guys need to feel freedom from judgment to help them open up emotionally.
3. Do not smother him. Guys do not like it when they feel trapped by another person. Fawning all over him may actually push him away. Even if he does have feelings for you, he will put off telling you because he may not enjoy how clingy you are.
Be patient. Trying to move too quickly may frighten him and cause him to be less open around you.
Do not bombard him with text messages. You should not be the first person texting him in the morning and the last person texting him at night. Make sure that the text exchanges between the two of you are more equal than one-sided.
He should initiate hanging out with you at least half the time. If you ask him to hang out and he gives you a reason why he can't, let him be the one to ask you to spend time together next.
4. Avoid chasing after him. If you chase after a guy you like in hopes that he will confess his feelings for you, he might want to keep running. Being chased might be more exciting for him than confessing how he feels about you. He may start to really enjoy being pursued by you instead of being the one to pursue you! Lay off a little bit and let him have the opportunity to realize that he does not want to lose you. This will help push him into telling you how he feels.
Don't show up to his work or house without being asked.
If you cross paths at a party, don't follow him around all night. Mingle with other friends and show that you can hold your own.
There can be only one person chasing, and you don’t want that person to be you.
5. Be authentic and humble. Pretending to feel confident or boastful in order to hide your true feelings will make a man feel uneasy around you because he’ll sense that you’re pretending. If he feels uneasy, he can’t be honest with you about what he’s feeling. Be confident about who you are, but don't brag or come across as arrogant because it will push him away.
Do not talk down about other people or talk about how great you are. Instead, offer compliments, listen well, and remember it is okay to be wrong.
If he hears you being judgmental about other people, he will fear that you will judge him, too.
6. Flirt a little bit with his friend. If you focus your attention on one of his friends, he might start to fear the idea of losing your interest to someone else and quickly let you know he is into you. You do not have to go too far with your flirtation, just engaged in a fun conversation with one of his friends for the evening to stir up some jealousy and that is all it may take. Here are some questions you can ask his friends:
"What do you like to do with your free time?"
"What do you do for work," or "What type of job do you want to do in the future".
"What are your favorite movies?"