How to Get a Guy to Open Up
Men are notoriously difficult communicators, a fact which women have lamented from time immemorial. The male half of the species is socialized to equate silence with strength, and they rarely show their true feelings for fear of seeming "weak." While nothing could be further from the truth, it takes a little work to get a guy to open up and talk about how he really feels. Trust and acceptance are the watchwords: by establishing an atmosphere of safety, a guy will relax and be more inclined to open up.
Instructions
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Watch for nonverbal signals suggesting how he feels. Most people have "tells"--little twitches and emotional tics which appear when they feel a certain way. Your guy may clench his teeth when he feels upset or furrow his brow when something saddens him. Learn to identify which cues are attached to which emotion, giving you some idea what he's feeling.
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Adopt a safe and trustworthy space. Smile at him, look him right in the eye and touch his hand if appropriate. You want to let him know that he can say anything to you, and radiate feelings of empathy help him do that.
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Open up about yourself. While you should never reveal more than you're comfortable with, a willingness to talk about your fears and concerns makes him more willing to talk about his. Be open and honest about your worries--asking him for support, not advice--which signals to him that you trust him. That helps establish the right atmosphere for him to reciprocate.
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Offer him a way in. Many guys won't say anything about their feelings unless prompted, leaving it to you to instigate the conversation. Tell him that he looks troubled or upset and ask him if he wants to talk about it. Do so in a private space with just the two of you, away from the public eye. Don't badger him if he refuses, but let him know that you're there for him and will listen to whatever he has to say.
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Tips & Warnings
Every guy is different and not all of them respond the same way to overtures of trust. Tailor your approach to fit his particular comfort zone, rather than applying a catch-all solution to the issue.