It's a hit or miss for me...sometimes I can help the guy to open up just by breaking the ice...but normally if they can't open up to me...i drop them, because it's not fun when you can't just talk to someone.

Frame questions in a way they have to think about like "what do you feel about that?" instead of questions that allow a yes or no response. Ultimatley though it is only the guy that can decide to open up, express his feelings and have a serious conversation.

Speaking on behalf of a lot of guys I have known, this kind of conversation often borders on interrogation to us. Guess what? Guys are generally not talkers. We can't sit down in front of you and unload like one of your girlfriends and it is damned unfair to expect us to do it whenever *you* want to have an emotional conversation. You gotta take it when we are ready to dole it out. Guys are activity oriented. We bond with our buds by *doing* things together and establish a base of common experiences. During the course of those activities, we do share emotional bits, but they come in drips and drops; put out there to see how it is accepted before sending another one out. Here's another hint: these events seldom occur when guys are looking each other in the face. A lot happen while working on an engine, at the rifle range, in the hunting blind, or on the fishing boat. In other words, when we are not looking at each other. Don't try to make us look at you when we open up. Get us moving, working, using our hands. That often allows us to open our minds for other things.

well i guess im different bc i wanna open up to girls but i get scared of what they might say or do, you know i just dont wanna get shot down

Men in our culture are generally conditioned to avoid conversations where they may be called upon to express how they feel. That call for openness goes against the grain of many years of cultural programming. That doesn't mean it's impossible to have deeper conversations, but it's a good idea to know what you're up against. The first thing you need to do is adjust your expectations, and notice your judgments about it -- you think they SHOULD be able to open up and talk about their feelings, yes? But the fact is, that's very difficult for many men. Unless their parents and environment encouraged and modeled that behavior, they probably haven't learned to be comfortable with such things. It doesn't mean he's a bad person, or doesn't love you, or is somehow broken, it just means he has been conditioned like many others. So don't criticize him for that. It's normal behavior. Next bit: you can help by listening well and "leading" the conversation. Stay attuned to his body language, any hints dropped, read between the lines. Don't attack, but gradually and gently suggest the direction he can move toward. This takes time, persistence, and patience. The idea is to provide guidance and a "safe" environment for him to begin to learn the vocabulary of his own internal state, and learn that it's OK to talk about that stuff. It's good to have a sense of humor about this too, and let him know what you're up to, but not be oppressive about it. "I'm gonna teach you what feelings are if it takes 10 years! :)" ... with a SMILE. That way he knows that a) you're working with him, not against him b) there's a long term project going on c) it's ok if he doesn't suddenly get with the program and d) you're not going to dump him next week because he can't communicate. Good luck. It's a big job.

If you want some really good chats, go to your girl friends. If you really want a guy that is opening to conversation, find a guy who is open to conversation. This type of guys are rare, but they do exist. You will find it easier to look in groups of acadamics, professionals, intellectuals...they need to be very well-educated.

just start talking to him