How To Ditch Small Talk
And Get Deep Quickly

We all know that celebrities rehearse their same stock, boring answers to common interview questions. So why is it that Howard Stern is one of the only radio hosts who gets them to ditch the PR talk and reveal deep, dark secrets?

Some people say, “Yeah, well it’s Howard Stern…” as if his specific biological makeup allows him to be the only person who gets people to open up. When really, he’s worked very hard to learn how to push people’s buttons and allow them to be vulnerable.

It’s a skill he’s refined for decades and I believe anyone else can master it, too. 

We’re Bored Of The Masks

For example…

I’ve gotten girls to talk about their craziest sexual experiences and fantasies after 30 minutes of meeting them at a party.

I’ve had phone sex with women after 2 hours of talking to them on the phone and never seeing them before.

I talked about illicit drug experiences on the very first night I met my girlfriend.

And I’ve made best friends with complete strangers by shamelessly sharing my dark and dirty sense of humor.

We are hard-wired to trust people. We are dying for the opportunity to connect and talk about real shit. Almost nobody wants to endure through more small talk nonsense. It’s so much more interesting to express ourselves openly and hear the same from others.

You just have to cultivate that atmosphere and invite other people to join in.

The two main ways to do that are by building…

  1. Comfort – You need to provide a judgment-free environment where people can express themselves without shame.
  2. Trust. You need to demonstrate integrity by being honest and direct. So even if someone disagrees with your opinions or values, they feel comfortable opening up, too. When people sense you’re bullshitting or just trying to impress them where they will hold back.

To accomplish this, follow the guidelines below.

Don’t Put Down Their Interests Or Values

When someone shares something personal with you, they’re being vulnerable. They’re putting their true selves on the line, and that can be terrifying.

The worst thing you can do is make fun of someone at a time like that. They let their guard down and you don’t want to make them feel rejected.

What about friends who always tease each other?

That’s usually a guy thing and I wouldn’t use it as much with women. Also, best friends do this with each other because they’ve already built a deeper trust. They know it’s all in good fun and that the other person cares about them. When you are just meeting someone you don’t have that same bond, so it can be harder to pull off.

If you do want to tease someone, make sure it’s not about anything serious. I might poke fun at their reality TV obsession, but not their career choice. I’ll also show interest and ask them another question right afterwards so they know it really was a joke.

Moreover, if you disagree with something, you don’t have to keep it to yourself. Be honest but tactful. Convey that you understand and respect their opinion but feel differently.

Give Sincere Praise

I write about this often, but so many people don’t utilize powerful compliments.

We all want to feel desirable, interesting, smart, and likeable. A meaningful compliment can make us feel awesome. But it has to be authentic and not just to gain approval – people can easily pick up on that.

You have to compliment someone when they’ve earned it by telling you something you truly value. Then you have to say why you find that worthy of your praise. Saying “oh, that’s cool” or “nice” isn’t good enough — it’s generic.

It’s the difference between…

“Good for you.” vs “Not many people ever take a chance to pursue their true passion. I think that’s really brave – I’m rooting for ya.”

Be Genuinely Interested

If you’re just in conversations to talk about yourself, you won’t get far. Conversation is a flowing dialogue where two or more entities are learning about each other.

A lot of clients have told me they don’t usually care about what other people talk about. They only care about their interests and are bored with anything else.

All I can tell you is that if you keep that mindset, you’re going to struggle to make connections. You’re betting on finding someone who’s exactly like you, which is completely unrealistic.

You have to maintain a sense of wonder in life. You have to develop a thirst for learning about different passions, hobbies, and people’s unique personalities and histories. This will make you more well-rounded and able to converse with all types of people in all types of situations.

You also need to physically demonstrate that you’re interested in the other person.

Maintain strong eye contact – glancing around the room will quickly show that you’re not actually paying attention. Speak passionately and excitedly. Be animated with your expressions. Stay present in the moment and not in your head.

Delve Into Personal And “Dirty” Subjects

People aren’t going to tell you personal details about themselves until you ask for them.

A client of mine was on a date with a girl whose father had recently passed away. When she told him, he awkwardly responded, “I’m sorry…” and left it at that. I asked him why he didn’t say anything more and he replied, “Because that’s personal.” I said, “That’s the point!”

Don’t be afraid to get to know someone past surface level, even about sensitive subjects. I would’ve asked…

What was your dad like? How was your relationship? What’s your favorite memory of him? How have you been dealing with the loss?

You’ll never know whether or not she wants to talk about it until you try. She brought it up, and if she’s ready to talk, you’ll connect with her on a much deeper level than expected.

Don’t fear controversial or intimate topics like death, drugs, fears, and embarrassing stories. And you should definitely get into sexual conversation with women you like.

It’s better to be too forward than too timid — that’s how you learn someone’s boundaries. Let them tell you after you push that they’re not ready to talk about something.

You just have to ask good questions.

Open Yourself Up And Be Vulnerable

If you’re not willing to reveal your true self, flaws and all, what makes you think anyone else will?

Don’t be afraid to share your secrets and personal stories first. Be open and emotional about your past.

My friend’s teenage nephew was recently diagnosed with schizophrenia. He hinted that he was struggling but was embarrassed to talk about it.

My friend told her nephew about how she struggled with anxiety and used to be embarrassed about it, too. She found out she had a hormonal imbalance, was prescribed medicine that made her better, and that it was nothing to be ashamed of.

After revealing that about herself, her nephew opened up about how his medicine is not working as well anymore. He was starting to hallucinate and needed a higher dose but was scared to tell anyone. Because of that, we were able to get him the medication he needed.

Sometimes you’ve got to take a leap to get others to trust you.

Consider Swearing (Tastefully)

When Howard Stern first went to Sirius Radio, everyone thought he was going to be more vulgar than ever. It was the first time he could swear unfiltered on the radio.

Instead, he came out and said how he was going to be tactful about his use of foul language. He understood that cursing is an art. It can add emphasis, meaning, humor, and passion to conversations. But when you swear all the time, it loses its dramatic impact.

Some good examples are swearing in amazement at a person’s crazy story or increasing the impact of a punch line.

When someone drops the occasional f-bomb, we feel like they’re being real with us. It gives them character and depth. We often swear when we’re expressing our true emotions (such as frustration) and with our closest friends.

Think about every Academy Award-winning movie or cult classic – their best, most memorable lines often have cursing.

Use Dark Humor

The best comedians know how to say something that makes us cringe, laugh, and then feel slightly guilty — all at once. Off-color jokes that are politically incorrect and taboo are often the funniest and most thought-provoking.

George Carlin, Richard Pryor, Dave Chappelle, Tom Segura, and countless others have had the courage to joke about topics that most shy away from. Some of these subjects include inappropriate sexuality, fart jokes, physical violence, death, suicide, sexism, and racism.

Of course, there’s a fine line. You don’t want to talk about dead babies with someone you just said hello to 30 seconds ago. Also, people have varying levels of dark humor acceptance. A small percentage won’t enjoy it at all.

Your best bet is to start with more acceptable topics and if they react well, you can get progressively more controversial. In general, you should start subtle and then be more vulgar or blunt.

Also, you may want to wait until 5-10 minutes of conversation before dropping a dark joke. I was best man at a wedding a few weeks back. During my speech, I told the guests about the time the best man and I were out meeting women.

As a joke, he used the pickup line, “Hey girl, is your dad a beaver? Cuz DAAAAM!” It got a roaring laugh and lots of people complimented me on it later (including the bride’s father).

Don’t Brag Or Show Off

Studies show that doctors who use simple language and vulnerability when talking to patients are seen as the most personable. We want to feel like we’re talking to someone who gets us and is on the same level.

Similarly, the snobbier you act, the less relatable you are. You inherently make the other person feel like you look down upon others. Therefore, they become worried that you’re judging them and see them as less.

You don’t need to impress people or compensate for your insecurities. People who are genuinely awesome and confident don’t need to prove it. They let their actions, behavior, and personality show it for them.

You can talk about your hobbies, exciting stories, and what you own while being humble and not constantly talking yourself up. Share a little and let people want to inquire more about you naturally. Then it won’t feel like bragging to them.

Ditch the small talk. You’ll have more fun, engaging conversations and you’ll see just how willing people are to connect with you on that deeper level.