How to Start a Conversation With Your Boyfriend.

• Ask the open-ended question. This sort of question requires an answer of explanation; it cannot be answered with a simple yes or no. An example of this would be, "What did you have for lunch?" If he answers, " A sandwich," you ask him what kind of sandwich.
• This kind of topic is considered small talk. What your boyfriend had for lunch is not significant, but it demonstrates a connection. You want to know about his day. Handled correctly, small talk leads to conversation.
• Ask a small-talk question, which can be on any topic that concerns an action or event related to your boyfriend, requires an answer other than yes or no and isn't controversial. If you need to ask another question to clarify, go ahead. But don't be tempted to simply pelt him with questions in the hopes of getting him to talk.
• Move the conversation onto a related topic. For example, if your boyfriend had a hamburger for lunch, you could say, "Hey, did you know so and so was a vegetarian?" Ultimately, this could lead to a discussion on the merits and drawbacks of vegetarianism. How? After his obligatory grunt, ask him if he could go without meat for a whole week.
• Don't treat this like a serious "Our relationship hangs in the balance" conversation once you get a more substantive conversation started. The art of conversation lies not in articulating profound thoughts or reflecting on life-altering events. It lies in an exchange of casual musings, an entertaining volley of viewpoints, a trading of tidbits.
• Your goal is to have a conversation, not a debate. Your goal is to enjoy talking with your boyfriend and having him enjoy the time he spends talking to you. Remember, subconsciously, males are fed the idea that talking is the equivalent of sharing your feelings. 
• Your goal is to make your boyfriend comfortable with conversation. Once he masters conversation, the serious stuff will come more naturally.
• Be aware of the direction he's taking. If he's clamming up, move to another topic. For example, you could say you think Burger King has better hamburgers than McDonald's. You're pretty sure he's going to say he likes McDonald's burgers better. Get him to support his answer. You could say something like, "But they don't have secret sauce."
• You've moved from asking leading questions to creating discourse. Now, neither of you really care which franchise has the better hamburger, but this could lead to a conversation about fast food, marketing techniques, or even dating, as in, "Is going to Burger King really considered a dinner date?"
• Start a conversation with your boyfriend with small talk and follow through by discussing any topic in the manner of free association. Let the conversation take a natural course. Keep in mind that you do not have to keep up a running commentary, or fill every moment with conversation. Good conversation also creates comfortable silence.
• Don't be shy about saying, "I have something serious to talk about with you." The male of the species may not respond well to the idea of "sharing," but if he really is your boyfriend and you have, covertly, schooled him in the art of conversation, he will respect that you need to verbalize and that you need him to respond. The art of conversation teaches us all how to hold civil discourse on any topic, be it casual or serious.