I walked up to a prostitute and had to get her to like me in about five seconds or less. I didn’t do this because I wanted to sleep with her. I did it because it was my job.

For about 2.5 years I had a job that I created for myself. I had to interview people at three in the morning on a Tuesday or Wednesday night and find out what they were up to?

Why a Tuesday or Wednesday? Because on a Saturday night I know what they are up to. They are hanging out, partying, whatever.

But if someone is out at three in the morning on a Wednesday night, there is usually a reason. And usually not a good reason.

Why three in the morning? Because I get tired and I go to sleep at 9pm. Once I was over a girlfriend’s house. She got upset at me because at three in the morning I wasn’t very excited and I couldn’t have sex with her.

So she kicked me out of bed and said, “I can go to the corner and find anyone I want. Get out of here!”

I left. And when I walked outside I was surprised how vibrant and exciting three in the morning was. There seemed to be a story, a dramatic production, playing itself out on every corner of the city.

I wanted to find out what was going on. But I was too shy. I couldn’t do it. I could only watch.

That’s when I decided to make it my job to find out.

I was a computer programmer at HBO, the television company. I pitched to them, “You need a website” (this was in 1995). And, “just like you specialize in original programming for TV, you should do original programming for the web”. I pitched a web show “III:am” about what goes on at three in the morning.

I went out every week for almost three years and interviewed thousands of people. Every week I’d take the top four interviews and put them on the web. After awhile, HBO gave me money to shoot it as a pilot so I shot a 45 minute episode.

I turned over every rock in the city. I went to every whorehouse, every underground gambling room, I went to jail, I found where all the undercover cops did their thing, I went to hotels that had no good news going on all night long.

But I was shy. How do you go up to a couple arguing in the middle of the night and interrupt them and say, “Hey, how are you guys doing?”

I’ve been chased. I’ve had bottles thrown at me. I’ve had famous actresses run screaming from me. I asked out girls the next day that I interviewed the night before.

But I was scared to death every single time the evening started and I was on the job. How was I going to find my ten interviews? How was I even going to find one?

Ask a question. People are constipated with facts. They are relieved to get rid of those facts. Ask them. “What are you guys up to tonight?”

Smile. Everyone wants a new friend. When I meet someone, the first thing I wonder is not whether or not I like them, but whether or not they like me. Smiling is the best way to let them know you like them. And be genuine about it. Fake smiles are creepy.

Listen. If someone says, “I wasn’t always using crack. But now I’m just looking for a place to live” ask them when they started using crack. Why do they like it? Do they plan on stopping? Where do they usually sleep and how come they can’t just go back there? Every time someone says anything, it’s the clothing that covers a cold secret. Dig until you find that secret because that’s the gold.

Shut down your brain. Your brain doesn’t want to talk to strangers. It wants comfort. It wants you to be safe. We have the same genes now that we had 40,000 years ago. Talking to someone outside your tribe might have gotten you killed. Hence, your brain will scream and shout and freeze you and cause you actual physical pain if you want to talk to someone new. It takes practice to ignore the brain. Curiosity somehow bypasses the brain. So if I see, for instance, two people arguing, I’ll focus on the curiosity instead of the pain that appears as I start to approach them.

Dress nice. Not in a suit. Just be clean. This seems obvious but it isn’t. I will tell you a secret. Don’t tell anyone. Sometimes I lie in the sidewalk near where I am staying and I ask people for money as they pass. 99% of the people ignore me and walk right past me. I do this to practice talking in uncomfortable situations. I’m 48 years old. I shouldn’t do this. My kids would be horrified. There’s crap and pee on the sidewalk when I lie down. But if you stand straight and dress nice and smile, people will stop and talk.

Everyone has it hard. I watched an interview show the other day. A famous newscaster was on the street interviewing people. And then sometimes she’d look at the camera and make a face because she doesn’t like who she is interviewing. I thought this was nasty and horrible. And the interviews were horrible. From the moment our feet finally leave the inside of our mother’s womb, until the day we die, life is a battle. Battles could be glorious but they can also cause much suffering. Respect everyone’s battles. Respect that everyone has it hard, or harder, than you do. Don’t fake sympathy or sincerity. People can smell that. If people feel you understand their hardships. They will like you.

Relate. One time I was interviewing a black transvestite prostitute. She told me her parents had been in jail since she was a kid and she got into trouble when she was young and raped in every juvenile detention center she was in until she was so hopeless confused as to her sexuality that she didn’t know if she was a man or a woman. And now that she is halfway in between, she was afraid to walk around during the day and have people stare at her. I had no way to relate to her at all. Nor would I give her the disrespect of feeling bad for her. She started talking about how the police were getting more aggressive. I could relate to authority sometimes preventing me from living the life I want to lead. I was able to ask her how she survived despite the police forcing her into a smaller and smaller box for her to live her life. So she talked and talked. Finally someone to talk to.

Interrupt. I do a podcast. I’ve interviewed hundreds of people. But the one hour I get to spend with that person is the only time I get to talk to them. And they often have their canned answers. You have to interrupt. I tell them, “I’m sorry but if I get insanely curious about something you say, is it ok if I interrupt?” People always say yes. When Tony Robbins says, “And then Bill Clinton called me and….” …. “Wait a second! Why is Bill Clinton calling you?” I will never ever again get a chance to ask that. So interrupt and ask when your curiosity pushes you.

Make them laugh. I give lots of talks. I want people in the audience to like me. I also used to go on lots of dates. I wanted my date to like me. Here’s what I’d do every time: watch standup comedy for several hours befo*****d. This seems lame but it works. We each have mirror neurons. This means we can learn by watching. If I never climbed a ladder before but now I watch someone climb a ladder, I can now climb a ladder. If I watch standup comedy I won’t be a standup comedian but I can talk better, I can be a little funnier, I can do more things with my voice and face, I’m more at ease. This works every time and is my biggest crutch.

Be yourself. This seems like a cliche. Not because it’s so easy, but it’s so easy to say and so hard to do. How do I be myself? I try very hard not to brag. Ultimately, we are all beginners at this thing called living. I barely know how to do it. I’m a simple explorer in this dense thicket of jungle. That is who I am. People like explorers. People like wanderers.

We’re all on this journey together. And it’s such a pleasure to find someone, for even just a minute, to hold hands with and kiss.

Source: https://www.quora.com/How-can-you-ma...inutes-or-less