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Find someone you feel connected to and who you feel a strong connection with. It's difficult (though not impossible) to start a meaningful conversation with a stranger or acquaintance. It might feel more comfortable to start a meaningful conversation with someone you've known for a while or already have some closeness in your relationship. You might not want to start a meaningful conversation with someone who's often argumentative or focused on always being 'right'. Think about someone you can engage with and share both speaking and listening. A meaningful conversation will often occur within a context that makes it meaningful. While some meaningful conversations can happen spontaneously, others may require some planning. Especially if it's difficult to find time to meet up, choose a date and a time where both you and the other person can be present and fully engaged. For example, don't have the conversation when one or both of you have a time constraint. Avoid busy or stressful days so that each person feels comfortable and not preoccupied or stressed. When talking, you don't want to be interrupted by surrounding noise. You probably also don't want prying ears overhearing your conversation. Find a quiet place where you won't be disturbed or interrupted. This might include somebody's home or a private meeting room. For example, a restaurant may not be ideal as you may be interrupted or overheard. Look for a place with minimal distractions. Consider turning off your phone or the television so that it doesn't interrupt your conversation. If your conversations are often scattered, disorganized, or tangential, you can pause to talk a moment to organize your thoughts. This helps keep the conversation on track, and can give you a confidence boost as well! If you know you're going to have a difficult conversation and want to prepare well in advance, you can also try writing down what you want to say to organize your thoughts! Put some effort into starting the conversation, especially if it's a difficult topic. Decide on how you will start the conversation and what words you will say. Whether you enjoy it or not, small talk can help to open a conversation and make people feel more comfortable. Starting a conversation with something deep might be jarring or unexpected, so warm up with some small talk first. When you and the other person appear comfortable, bring up a more substantial topic. For example, ask how the person's day is going or briefly talk about the weather.
Choose who you want to speak with. Choose an appropriate time to talk. Find a quiet place. Collect your thoughts before you speak. Start with small talk.