All in One..The best: Mastering the Art of Conversation

1
Foster your curiosity about people. Wherever you go, try to observe people, and ask questions about them. I wonder what his parents look like? I wonder what her favorite color is? Is he from around here? Is she the girl I saw at the movie theater last week? It will take some conscious effort, but you can't be outgoing if you don't give a hoot about people.
- Marlene Dietrich is credited for saying, "The average man is more interested in a woman who is interested in him than he is in a woman with beautiful legs."^[1]Whether it's romantic relationships or just friendships, she was right. People love it when others are interested in them. We're all a little bit selfish; getting interested in others takes advantage of this.
2
Smile at others. Make it a goal to smile at one person a day. It can be anybody, and it can be the most subtle of smiles. A quick glance paired with a smirk -- then run away if you want! The more you do it, though, the less scary it will be. Eventually, you'll want to get to a point where you smile instinctively whenever you make first eye contact with someone.
- It's easiest to smile at someone when they walk into a room, or when you walk into a room, because it's a simple friendly greeting and it doesn't seem as random. If smiling out of nowhere makes your creep-dar go off, start with introductory smiles.
3
Ask people questions. The standard "How are you?" doesn't really count, because people use it as a greeting rather than a real question. If you've already exchanged eye contact and smiles with someone, and you're close by, start off with a question. This is where the curiosity and interest in others comes into play. Here are some ideas:
- How do you like that book/magazine? My friend loves it.
- You look familiar. Do you work at the movie theater?
- Is that an Egyptian baby harness?
- What do you think of this as a gift for a mom?
  - Most people would never approach a stranger (we're all a little bit selfish and we're all a little bit shy), but that doesn't mean we don't enjoy it. Think about if a nice guy/girl walked up to you and asked if you would buy the trinket in their hands for your mom? Would you be intimidated or turned off? No. Would your day be a little more eventful? Yes.
4
Give compliments. If you're interested in people, you're bound to notice little things that you like or appreciate. Make sure they're genuine though! A forced compliment can be spotted through rush hour smog. Think of something like:
- I've read that book. Great choice!
- I love those shoes. They go great with that skirt.
- Is that a hazelnut latte? Nice -- that's my go-to every Monday morning.
5
Ask a question before you make a comment. There's probably about 49,075,389,475 awkward conversations going on right about now on this planet (the stats are forthcoming). Yours are not the only ones. The culprit for about 49,075,389,474 them? Dead air. How do you avoid dead air? Questions.
- Let's say you ask someone, "How's that book so far?" They say, "Good." Well, for starters, they're the ones who are killing the conversation, not you. Instead of saying, "I'm glad you like it," (where the conversation would end there), say something like, "Was Oprah right?" or "Have you gotten to the part where X happens?" or even "I need a new book -- have any suggestions?"
6
Search for a commonality. First conversations between people are all about what the two parties mesh on. In order to find out what you can talk about, you gotta probe for things you have in common. If you work together or have mutual friends or have anythingthat links you together, problem solved. Talking about the boss or your friend Julia or that cooking class will open up further topics of discussion.
- If this person is a stranger, start with the scenario. Remark on the coffee shop, the wait for the bus, the loud group of protestors down the block -- whatever.
  - Remark on something about them if you can go somewhere with it. Saying, "I like your glasses" only works if you can say, "I got LASIK last year and miss them in a weird way" or "I own a glasses shop -- want a discount?"
7
See what excites them. If person A is dead set on talking about thermodynamics and person B is dead set on talking about Italian coffee (who knows why?), the conversation isn't going to go anywhere. One of these people has to latch on to the other person's interests. Let that person be you.
- When you're making that awkward small talk, probing for commonalities, try to notice when the other person perks up. You'll be able to hear it and see it. Their face will be more expressive (and so will their voice) and you'll probably see movement in their body. Humans all show excitement in similar fashions -- how you would see yourself talking about one of your passions is probably taking to how they talk about what excites them.
8
Master eye contact. This is key to being a good conversationalist (which is the majority of the battle in being outgoing). If you don't make enough (or any) eye contact, the other person will feel invisible and get the sense that you're elsewhere mentally. If you make too much, the other person they'll feel probed and uncomfortable. Is that specific enough for you? Let's narrow it down:
- Make eye contact when you're asking questions -- you're acting interested, remember? But when you're answering, a good rule of thumb is to make eye contact when you want to convey something (that a compliment is genuine, say) -- if you're talking about your day or making some off-hand comment, it's okay to stray.
9
Note your body language. People are intimidated by others to some degree, whether they admit it or not. Imagine seeing your best friend in a corner, talking on a cell phone with his/her legs crossed, arms folded, and possessing a very stoic expression. Even though it's your best friend, are you going to initiate a conversation? Nope.
- Most of communication isn't verbal. To show that you're outgoing and welcome conversation, keep your body open, your head up, and an ever-so-slight smile on your face. Resist playing with your phone or otherwise occupying yourself.
- Commit to your actions. A hesitant handshake conveys that you're nervous and unsure. If it's appropriate to laugh, laugh! Whatever you're thinking about doing, do it. Otherwise, the struggle will be visible and deterring to both you and the person you're talking to.

Thinking Positively, Effectively, and Confidently

1
Want it...for the right reasons. Changing your personality is hard. It's a huge deal. Legitimately wanting it -- needing it practically -- is the only way it'll come about. In your case, why do you want it? You do want it, right? It needs to come from a source within you -- not what others tell you to want.
- There is nothing wrong with being an introvert and being shy. If you want to be outgoing to fit in, it probably won't happen. Instead, think about why being shy bothers you. Maybe it's just something that coming to terms with could solve. Being you and being shy is much better than not being you and feigning extroversion.
2
Pretend. Humans are programmed to look to others for leadership. We crave it. It takes the responsibility of our shoulders. Because of that, those who are confident practically get away with murder. If they seem confident and credible, we don't question their actions or intentions. Let that be you. If you pretend you're a social party animal and are firm in your party animal convictions, no one will be any the wiser. Act like you belong and eventually you will.
- This goes back to committing to your actions. If you have to go into your boss' office and fake sick to get the day off work, he's not going to believe you if you're not hacking up a storm. You can fake confident in much the same way. The beauty of it is that others will take your behavior at face value because they don't know any better. It's like a joke you get to play on the entire world.
3
Practice self-awareness and an attentional to detail. Taking an honest look at yourself and what's standing in your way is the only way to grow. When you find yourself in situations that rev up your shyness, what is it about that situation that does it? How does your body respond? What are your inclinations? Figuring out how you operate is the first step to taking charge of your reactions and saying, "No. We're doing this my way."
- On a similar token, be aware of others. If you spend too much time in your head, you'll miss those obvious conversation starters. Maybe that guy has a huge Miss Piggy tattooed on his arm and you didn't even notice! Being aware of others (how they act, how they're feeling) will help you tune into how to approach them.
4
Lower your expectations. Jimi Hendrix was not a guitar god over night. Thomas Edison didn't invent the light bulb on his first try. You won't become a social sleuth in no time flat. That's just how the world works. So lower your expectations and set smaller goals. Just getting out there and around the water cooler is enough. Save cracking jokes for a little ways down the line.
- Only you know what's a challenge for you and what's not. If you had to put "outgoing" on a scale of 1-10, where would you fall? Now, what behavior can get you just one point higher? Concentrate on that before you expect 9s and 10s.
5
Control your inner dialogue. Negative self-talk is a terribly powerful thing. When we get in our heads, it determines everything. Even research says that happy, positive people are more successful.^[2] In order to truly conquer those demons of shyness, you have to monitor that self-talk. You can't let it talk you out of making progress.
- It's natural to think, "Ohmigod, I just made a terrible mistake" when we just commented on our not-pregnant acquaintance's pregnacy. That stuff is going to happen. The only thing you can do is get back up. Failing is okay. Failing is going to happen. It means nothing. There is always going to be another opportunity to impress someone. You gotta get back up and brush yourself off, hopefully better for it.
6
Know it's a skill. Sometimes it seems like those social chameleons we all know were born with it. And, true, some people are naturally predisposed to being more inquisitive and gregarious -- but by and large, it's a learned thing.^[3] Your brain is plastic. It can be molded. Those people that have it down have been practicing for years.
- If you know some outgoing people (and you do), ask them about their extroversion. Were they always that way? Do they ever feel like they have to try to be outgoing? Do they have their own versions (albeit small) of social phobia? The answers will probably be no, yes, and yes. It's just something they've decided to take control of.
7
Think of past successes. When we're at a party and we're huddled in the corner, the natural thought process is to think about how lame and unsocial we are. Let that happen for a minute or two and then start thinking of all the times you socialized successfully. Surely you're outgoing around family and friends! What's really the difference between those situations and this one? Whatever the difference is, it's most likely in your head.
- Thinking of all the times we did what we're currently afraid to do shows us that we are capable and makes us more confident. So rack your brain. Find a few social achievements and latch onto them. The next time you're at a party, pull them back up and channel that person. After all, they're all you.

Making It Easier

1
Set goals. Being outgoing is a tough goal to reach because it's so based in the abstract. Losing weight or being vegetarian is something that can be measured or accounted for -- being outgoing is more relative and intangible. So instead of telling yourself to be outgoing, set goals to make conversation, talk to strangers, or to smile at more people every day.
- Start out small. Go for making small talk (or if that's too much, just smiling) with one stranger/acquaintance a day. Say "hi" to someone on the street. That barista that you've seen every day for the past three months? Ask her her name. These little victories will keep you going and make you feel ready for loftier challenges.
2
Master a hobby. Everybody needs something they're good at. When we're really, really good at something, we feel pride and confidence globally. After all, if we can do this one thing, who's to say we can't do something else? And on top of that, it gives us something to talk about!
- And it makes us interesting. If you didn't catch that, being devoted to a hobby makes us more confident, gives us something to talk about, and makes us fun to talk to. As if you needed that many reasons to get your creativity on.
3
Join a club. Once we get out of college (or when you go to classes that literally have 500 students), it's hard to meet people. Even in high school and when we're younger, sometimes it's hard to meet people that we jive with. You can be surrounded by others and still feel very alone. To alleviate that, join a club! You'll find people that have your same interests -- or at least one!
- Remember how finding common ground is an important part of starting and keeping up conversations? Clubs (whatever form they're in -- groups, teams, etc.) are the perfect way to sidestep that part. Whether you're in a book club, an intramural softball team, or a fitness class, it's sorted. You have the first thing to talk about practically rolled out on a red carpet for you.
4
Put effort into your appearance. As much as the world shouldn't be so, it is: appearance matters. Lots of people are self-conscious about how they look, so they make it a point to surround themselves with others that fit in (so they feel they fit in, too). In order to be welcomed with open arms into any group (or just with one person), you gotta at least look like you're aware of the outside world.
- This is not advocating 4-inch wedge heels and a mini-skirt or Sperrys and a muscle tee. Heavens no. This is advocating showering, shaving, brushing your teeth, wearing deodorant, and not getting dressed in the dark. Somewhere between walking out from below a bridge and walking off the runway is a good, happy medium.
5
Stay current. Even the most outgoing of people clam up when they walk into a conversation where they haven't clue one about what's going on. To avoid feeling like every conversation is a conversation amongst brain surgeons/rocket scientists/socialites, stay current. When you know what's going on, you're more likely to chip in your two cents. Read the newspaper. Notice trends on Facebook. Pick a website to get your news from. Watch TV. Simple as pie, really.
- Most people won't be talking about brain surgery or rocket science -- they're probably talking about the government, that new movie out, or that one celeb that just won't go away who's famous for nothing anyway. These conversations are easy to bust into if you're in the loop and often being in the loop just means spending an hour or so a week watching a finale, reading an article, or listening to the radio.
6
Work on your existing friendships. Make sure to improve friendships with existing friends and the people you meet. Not only will you be more connected, but you'll be growing and gaining new experiences to share with both these groups of people.
- Old friends are good practice. They can introduce you to new people or accompany you to places you would never go alone. Don't ignore them! They're your bread and butter. They're probably going through similar things, too!
7
Take risks. Using the previous steps, you'll be reaching out to people and practice makes perfect (at least, it makes habit). Soon what you once considered a risk will just be Tuesday. You don't have to be totally confident in order to be outgoing; and whenever you do feel self-doubt holding you back, think of people you know who have their insecurities but are still friendly to strangers anyway. If they can do it, so can you, right?
- Put yourself in environments where there are lots of people you don't know and plenty to talk about, like a book or music store. There will be times when some people are cold and unresponsive and that's normal (we all have our moods)! Don't take it personally. And there are times when you'll mess up and feel like a fool - and that's normal too! Just laugh it off and move on.
- Make sure you are enjoying yourself. The easiest way to be more outgoing is to make other people feel confident and natural around you. HAVE FUN!

Being a Social Butterfly

1
Talk to anyone and everyone. Now that you've been debriefed on the art of conversation, you need to use it with people from all walks of life. A truly outgoing individual only needs a nearby heartbeat to get started on their social game. At first you'll be uncomfortable talking to people who you've deemed "different" than you, but soon you'll realize that that's all really just in your head. You have something in common with everyone -- we're all human.
- Keep on the lookout for people that used to be like you -- a little bit more reserved. Most people are just looking for someone to pave the road for them so they can run down it. Start a conversation and you'll be surprised where others will take it. Even if they're reserved, they'll appreciate someone taking the time to express interest in them.
2
Introduce people to each other. Part of being outgoing is being the glue that holds a group of people together. Not only do you hold them together, but you bring them together. Very literally! Once your outgoing self takes over (and it's there somewhere), you'll have friends and acquaintances from different areas of your life -- what happens when they get in the same room...?
- You go into action, that's what! Introduce all your friends together to ease the social awkwardness strangers always unnecessarily sink into. Think about what you know about each person -- what do they have in common? When you're talking to Janice from the yarn shop, take a moment to call out, "Hey, Steve! This is Janice. We were just talking about that new band at the Factory last night. What'd you think?" -- knowing full well they both love music. Boom!
3
Fill awkward silences. How many "parties" have you gone to where a group of 10 or so people is sort of sitting around, not really talking, once in a while commenting on the food, and then either everyone slowly sifts out and leaves or that one person arrives and all of a sudden the day is saved? Probably somewhere around "too many to count" and "hopefully never again."
- You can probably tell where this is going...that person can be you. When you're in a group of people, start talking. Get going on something everyone can laugh about. If it has to be you, so be it. (Studies also show that embarrassing yourself leads to others liking and trusting you more, so there's that.)^[4] If that's not working, start a game. Whether you're picking up a cheeto and balancing it the long way on your nose or starting some heated political debate, well, it's certainly better than everyone staring at the spinach dip!
4
Get the party started. This is sort of like filling awkward silences, but preemptively. You want to fill the silences before they even have a chance to get awkward. There's no black and white way to do this -- every party is obviously different and every group of people will be receptive to different things at different times, but you can arm yourself with a few weapons.
- Think about the group of people. Will bringing a specific drink or game be sure to keep things alive?
- If you arrive and things aren't bouncing, think of what you have at your disposal. Could you set up some entertainment or change the music?
- Most of the time, people soak up others' vibes. If you're excited to be there, other people may get excited to be there too (peer pressure!).
5
Host parties. You can go to parties, sure, but the true test doesn't come until you're hosting them yourself. The great thing about this is that clean up will be the hardest part. With an assembled group of people, it should take off on its own.
- Since you're the host, your duties are mainly providing ambience, foodstuffs, and conversation. If not everyone knows everyone, be sure to keep those on the outskirts of the group included. Talk to everyone, make sure they're all contented, grab a drink, and enjoy yourself.
- You know how many articles wikiHow has about parties? Tons (the actual number).
6
Run for something. Once everyone knows your name (and they're always glad you came), you might as well do something with your social network. Run for something. It doesn't have to even be political. If you're wondering why, it's because running for something will get you to meet even more people. People who are also super connected.