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Starting a conversation with an unknown person will seem less risky and more acceptable to everyone there. Some situations seem easier than others, especially when initiating social interaction. Supermarkets or banks are more often than not among the worst places to initiate a conversation with a total stranger (people just want to get their groceries and be done with it). Coffee shops, sporting events, and community centers can be great places to start talking to great new people.  To meet new people, try joining a group such as an amateur sports club or a book club. A fitness class is often a great place to start a conversation. You can also look for groups online to find meetings of people interested in the same things as you. Websites like MeetUp.com are great for that. Ask your barista how their day is going. Thank the mailman as he passes by, or ask a co-worker how their weekend went. You don't have to dive into deep, invasive, and consuming conversations immediately. Start small. Remember, there is no downside to saying 'hey' to someone. You will most likely not see them again, and these low-key conversations are the best to practice with. Approach your subject with open body language and appear to be interested in getting to know them better. This often is a good opportunity to have a meaningful conversation.  Be confident when approaching a person. If you are too nervous you may make the other person nervous too! Remember to put away your cell phone. Checking your phone all the time during a conversation annoys people, and makes them think you're more interested in your phone than you are in talking to them! If the encounter went on well, take note what you did right and do try to repeat this in the future. If things went poorly, mentally assess the situation to determine what exactly you did that wasn't all that impressive.  Did you approach someone who appeared to be busy with something or who was displaying closed body language? Was your own body language open and inviting? Did you start the conversation with an appropriate topic? Your social skills will improve with practice. The more you communicate and interact with people, you will get better at it. Try not to let negative social interactions get you down. Oftentimes such encounters are not your fault. Remember that there will often be setbacks as you work toward improvement. Learn from the situation, and go forward armed with new knowledge. This is usually a safe, comfortable environment where learning to speak to people can be easier. You are not the only one there who wants to work on their speaking skills. Why not practice with others who are in the same boat? The very fact that you want to improve your social skills shows that you are an open, kind person who is willing to work on themselves. Surround yourself with people with similar goals to help you grow. If you suspect social anxiety is interfering with your everyday life, seek help from a certified therapist who specializes in Social Anxiety Disorder.
Find a place where people seem easy going. Start small, chatting with service people that helped you out to get started. Pick someone who doesn’t appear busy or uninterested. Reflect on how it went. Talk to more people. Join a support group.