How to Start a Conversation

1. Speak with clarity and purpose. If you're mumbling, it makes conversing a lot harder.
2. Reflect before speaking if it's your turn to talk and allow silence to also have its rightful place in your conversation. Don't be afraid of pauses – use them to change topics, re-energize the conversation, or to take a short breather even.
3. Relax. Chances are that whatever small-talk you're making isn't going to stick out in anyone's mind a few months from now. Just say whatever comes into your head, so long as it's not offensive or really weird (unless, of course, the person you're attempting to converse with is into weird stuff).
4. If you think of something in your head while you're talking, it's probably related.
5. It will help if you watch some TV, listen to radio shows, and/or read a lot – newspapers, magazines, and/or books. Doing this will ensure that you have some idea of what's going on in the world.
6. Remember and plan to share anything you like, think is funny, or find intriguing. This is a way of building up your own inner library of things that might be helpful to another person during a conversation someday. It can be amazing how you thread these interesting things when you least expect it, and make conversation an adventure instead of a dreadful task. If you take it to the next step and say things that you want the person to think of as adding value, and keep to yourself things that the person might not, you're actually honing your own personality to be appealing to the other person, and what is a greater act of kindness than that?
7. If you're shy, it is helpful to have thought about a topic or two in advance that you feel comfortable talking about.
8. A great entry into starting a conversation, especially for a guy approaching a girl, is to mention you can only talk briefly as you're meeting up with other friends. This relieves the girl of any fear of being uncomfortably stuck with someone she does not know, and gives you both an easy out if things don't progress well. If the conversation does progress well, you can always delay leaving your new friend for as long as you like. Remember not to overdo it, because she might think that you don't want to talk to her, but prefer to be with your friends.
9. Follow the lead that your listener is expressing. If he or she appears interested, then continue. If he or she is looking at a clock or watch, or worse, looking for an escape strategy, then you've been going on for too long.
10. Interesting and funny quotes or facts can lighten things up, and make way for things to talk about. You could also use a set of conversation starter question cards for inspiration.
11. If talking over the phone, keep the person involved in the conversation at all costs. If you can't come up with a good topic, try the "questions" game. Just keep asking them questions; random questions work just fine as long as they are appropriate. This technique can save a phone conversation. The questions should be open ended questions that do not require a yes or no answer. For example "How do you know the hosts?" This way you can ask questions about what they just said or follow up with how you know the hosts (for example) instead of acting as if the conversation is an interrogation.
12. Half of an effective conversation is the way you non-verbally communicate, and not necessarily what you say. Practice better non-verbal skills that are friendly and confident.
13. Take a mental note of some amusing things that you saw or heard througout the day. For example, something funny someone said, a fun activity you did with your friends, or anything interesting. This can give way to future conversation.
14. Watch some stand-up comedians or comedy shows to get an idea of how to start a conversation humorously. Usually, the leads you find will be funny, and you will not need much in common to talk about them.
15. Remember, whoever you are talking to, you always have something in common. We all experience the weather, like good food, and enjoy a good laugh. When in doubt, just talk to them about what they are there for. For example, if you meet them at a bus stop, ask them where they are going. If they are from out of town, ask them about their life at home.
16. To break the ice, a compliment is always nice.
17. People like to hear "hey, you look like my cousin!" or "Are you by any chance related to...?" Great conversation starter.

1.  Don't be overly invasive with your questions.
2. Watch out if you use tons of fillers like "umm" or "soo". It might make the person you're talking to feel awkward or obligated to say something. Instead talk slowly and pause. This will create a little tension and make your newly found friend more invested in your conversation.
3. Don't ever comment negatively on the person with whom you are talking, or anyone else; you never know if there is a personal attachment to the person you are criticizing.
4. Never swear, insult, disrespect, use racial, religious, and gender slurs in front of others
5. Never act arrogantly and pretend to be a Know-It-All when dealing with people.
6. Never ever interrupt a conversation between one or more people. Wait for the conversation to stop and then say something. Common courtesy goes a long way.
7. Make use of "please", "may I", "thank you", "could you" when someone is nice to you and when you want something. Being polite shows maturity and intelligence.
8. Don't always talk about your financial status in the presence of your new friend, especially when a guy has met with a girl.
9. Also remember that not everyone wants to talk. If the person shows signs of discomfort or loss of interest, you should not bother them.

Be confident; there are tons of people out there that would love to talk to you! ~Aiko