Reach out to the person you want to talk to and mention work or school. Ask them what their job involves, how long they’ve been there, and ask if they’ve done anything interesting lately. If they’re still in school, ask them what they’re studying and what they hope to do when they graduate.  Be sure to answer any questions if they ask about your job or education as well. Show genuine interest in their job, even if it doesn’t sound the most exciting to you. Use it as an opportunity to learn more about the person and the subject. People enjoy talking about things they’re passionate about, so ask the person what they like to do outside of work or school, and note any areas that sound interesting to you. See what their favorite thing about the hobby is and what they like about it. When they ask you about your hobbies, mention any that are similar to theirs first so you can hold a conversation about it. If you’re interested in one of their hobbies, ask them how to get involved so you can try it too.  For example, you may say something like, “Oh I’ve never tried woodworking. What’s the best thing to do for a beginner.” Make sure you don’t talk over the other person or talk only about your hobbies. Ask questions about what the other person enjoys so you can have a good back-and-forth dialogue. Many people share similar tastes in media, so talk about recent films or music that you’ve seen or listened to and gauge the other person’s interest. Ask them what content they’ve been enjoying lately and let them explain why they like it. If you both have seen or heard the same thing, have a discussion about it and talk about your opinions to keep the conversation going.  For example, you could say, “Have you seen the newest Star Wars movie? What did you think of the ending?” or, “What music do you like to listen to? Do you have a favorite artist I should check out?” Even if you disagree with their opinions, stay positive and say something like, “Oh, I never thought of it that way, but I understand your point.” That way, the other person will still feel engaged with the subject rather than being shot down. If you don’t know what the other person is talking about, ask them to clarify or explain what happens so you can get a better understanding of it. It’s okay to say “I don’t know,” if you’re unfamiliar with media they’re discussing. If you feel comfortable with the other person, you may ask about their past or what they want to do in the future. Ask them about funny things that happened to them, what their family is like, or goals they have. Open up about your own experiences so you can share them and connect with the other person.  For example, you may say something like, “Where are you originally from? Did you like it there?” or, “What did you want to be when you grew up?” Strangers may find it odd if you ask too much about their personal life right when you meet them. Only ask deeper questions if you both feel comfortable responding to them. Never try to “one-up” the person or try to impress them, since it may make them uncomfortable and want to leave the conversation. Look up current events in the news or on social media and mention them to the other person. Have at least 1-2 events that happened in the past week ready so you can pull them out in your conversation. See what they think of the news and ask them how they feel on the subject. Be ready to talk about your opinions as well since they may ask you the same thing. For example, you may say something like, “Did you hear about the new music app that just came out? I saw it on the news.”
Ask the person what they do for work or school so you can relate to them. Talk about hobbies that you both enjoy to learn more about the person. Discuss movies, TV shows, or books if you want to talk about pop culture. Chat about your past experiences if you want to open up to the other person. Ask for the person’s opinion on current events to engage them.