Write an article based on this "Give them a warm introduction. Carry the conversation in the beginning. Choose topics you know they can contribute to. Ask for recommendations. Opt for topics deeper than small talk. Ask open-ended questions. Manage awkward silences by changing the topic. Gauge how interested they are in the conversation."
Approach the shy person with a friendly face and tone. Avoid getting too close or rushing up to them; instead, be calm about the interaction. You might also ask them a question about themselves to break the ice and get the conversation flowing. For instance, you might say "Hey Terry! I'm glad to see you. Did I see you at the movies last night?" If you have never officially met them before, introduce yourself and tell them you're glad to meet them. If they don't know you well, the shy person is unlikely to begin chatting, so you'll have to lead the discussion. Be mindful of this during the interaction and don't expect tons of chatter from them. You can start off by saying something like "Did you know there were free donuts in the break room?" Don't be put off or insulted if they only provide short or brief answers at first. It may take them some time to warm up. Before or while you speak to them, make note of things they do well or things they like. If you know where they're from or things they're interested in, use this to make conversation. This helps ensure that they have something to talk about. You can say something like "So, you're from Fayetteville? I used to go there a lot with my mom. Did you like living there?" or "I noticed that you were wearing a Princess Leia shirt the other day. I really like Star Wars! What's your favorite movie of the series? A shy person may feel uncomfortable talking about themselves, but they may enjoy having conversations about other topics. You can get to know them by asking for recommendations for books, shows, movies, and fun activities. For example, if you notice them reading a book, ask them if it is good. You can ask if they have read the author before or if they have reading suggestions. If you're at a social function, you can ask the person what they enjoy doing in the area. Where are their favorite places to go? Shy people tend to dislike small talk, so avoid discussions of things like the weather. Instead, focus on things like their likes, dislikes, work, children or academic interests. You might say something like "I remember that you used to be really interested in WWII. Have you been to any cool museums or seen any recent movies about it?" Instead of asking questions that only require one or two word responses, dig a little deeper. Since shy folks tend to dislike small talk, ask them questions that will help you get to know them better and that'll allow them to talk about themselves. Ask things like "So, why'd you decide to move here?" or "How do you get up so early to work out every day?" Even when you aren't shy, awkward silences can be painful. Instead of sitting in silence, introduce them to friends of yours who are nearby, or have conversation topics on hand to continue your talk. You can even offer to go get them a drink or snack if you are at a luncheon/mixer. For instance, you might discuss school, work, or the latest political or social headlines. At large parties or social functions, it may be difficult to hold a long conversation. If the conversation stalls, ask the person if they want to meet up another time to continue your talk one on one. Even when someone is shy, you can still tell if they're engaged in the discussion. If they're responsive to your open-ended questions, looking at you, or smiling, they're probably interested. However, if they have their body turned away from you and have a blank facial expression, they might not want to be bothered. Give them their space if they're uninterested. Remember that that's okay - at least you tried. You can say something like "Well, I'm glad we got to talk, Josh. Hope you have a good day."