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Stay positive. Keep them talking about themselves. Be witty. Find common ground. Avoid over-sharing. End on a good note.
People are more likely to stay and interact with you when you keep the conversation positive. Don't expect that people will dislike you or try to get away. Keep the conversation positive, and keep yourself friendly and approachable. Even if you feel nervous or don't have the best self-esteem, try to come off as confident. Trying to back out of a conversation or coming off as fearful will make others want to leave the conversation early. If you're nervous, fake it until you make it. For most people, once they see that you’re willing to listen, they can talk for hours. In general, people like to talk about themselves, their ideas, and their interests. Use this knowledge to your advantage and keep the focus on the other person. Show an interest in what they are saying by nodding or responding with comments like “Really?” People are often charmed by people who make them laugh. However, they may not want to sit there and listen to joke after joke. Instead of using outright humor, offer a sample of wit that suits the context. For example, if the two of you are waiting, you might casually say, “Gee, if I’d known the wait would be so long, I would have packed a picnic lunch. If you hear my stomach growl, forgive me.” People are attracted to those who seem to “get” them so pay close attention to any mutual interests or opinions you have with the other person. Use this common ground to emphasize how you are alike and build a stronger connection with the other person. For example, you might say, “I feel the same way!” or “How ironic? I grew up in a small town, too.” Unless you want to inadvertently push others away, stick to light or neutral topics during your initial conversation. Although it’s perfectly acceptable to make a major disclosure with a close friend, it’s frowned upon to do the same with a virtual stranger. Over-sharing tends to make others uncomfortable.  It would be consider inappropriate, for instance, to tell a person you just met that you are dealing with a troubling medical condition.  Don't be afraid to show some vulnerability about subjects that naturally come up. This can help build trust. Sharing too much information all at once, though, can be off-putting. The key to an overall pleasant interaction with a stranger is knowing when to cut the conversation short. Check out their body language. Are they turning away from you or seemingly distracted by their phone or a book? If so, this might be a signal to part ways. Be sure to end the conversation in a positive light. For instance, even if things started to become awkward or quiet, it might be nice to make your exit by reminding the person of your connection. Say something like, “It was nice meeting you, Joy. I hope you think of me the next time you eat rocky road ice cream.”