Sometimes the best offense is a good defense. Look at it like the Hippocratic Oath of conversations: Do no harm.
We’re all terrible at realizing when we bore others because, well, we all think we’re just fascinating.
The #1 tip for never boring anyone comes from Scott Adams:Be brief, be positive.
If you’re always to the point and stay upbeat, it’s extremely hard for anyone to accuse you of being poor company.
But sometimes you do need to speak a little longer to make sure things don’t get stilted.
The Art of Civilized Conversation offers another good tip: Is anyone asking you questions about what you’re saying?
If not, maybe it’s time to end the story or ask the other person a question.
(More rapport building techniques are here.)

2) The Most Captivating People Are Often Good Listeners

Impressing people can be great but it can also devolve into status jockeying, one-upmanship and envy.
People love to talk about themselves and there are a dearth of good listeners.
Talking about ourselves—whether in a personal conversation or through social media sites like Facebook and Twitter—triggers the same sensation of pleasure in the brain as food or money…
You can make an excellent impression by saying amazingly little. Ironically, the people we like the most often say the least.
(Learn how to listen like a hostage negotiator here.)

3) Talk About The Other Person’s Interests

This is straight from Dale Carnegie and if you’re not that socially adept, this is as straightforward as it gets.
Why struggle to guess what most people might find generically interesting?
Ask people what they’ve been up to or what their hobbies are. Then talk about that. You’re now 80% of the way there.
If you know about the subject the similarity will bond you.
If you don’t, ask them to explain and be a great listener as they talk about something they love.
(More on the science behind Dale Carnegie’s classic here.)

4) Have Three Good Stories

Comedians don’t just talk about anything when they’re onstage. They have their act rehearsed.
You don’t just trot into a job interview and say whatever’s on your mind.
Always have three good stories on hand that reliably entertain, inform or engage.
Another tip from Scott AdamsPeople are generally more interested in stories about people rather than things.
Drama, gossip and reality TV are successful for a reason. We all find human behavior fascinating.
On the other hand, most people don’t want to hear about the features on your new iPhone.
(More on how to tell good stories here.)

5) Don’t Forget Charisma

It’s not all about the words. Some people are engaging but if what they said was transcribed, it would be unimpressive.
When you’re speaking emotionally, the words only account for 7% of what get conveyed. Seven percent.
Voice tone and body language are far more important.
One often quoted study (Mehrabian & Ferris, 1967) found that of all the information conveyed to another person when we say something that is emotional (not informational), only 7 percent is contained in the actual meaning of the words we use.
Laugh. Smile. Be passionate. Gesture. Modulate your voice. Don’t just sweat the words.
(Here’s how to be charismatic.)

6) Be Somewhere Interesting

Got a say in where you’ll be at, as with a date or meeting?
Pick someplace stimulating. Context matters.
In general, we’re lousy about realizing where our feelings are coming from.
Research shows excitement from any source is often associated with the person you’re with — even if they’re not the cause of it.
Why do people find musicians so captivating? The music and the crowd stimulates emotions — and we viscerally associate those with the band.
MIT Behavioral Economist Dan Ariely recounts a relevant study he did:
Why does this happen? Ariely thinks it might have something to do with “misattribution of emotions”: “Sometimes we have an emotion and we don’t know where it’s coming from, so we kind of stick it on something that seems sensible.” In other words, your strong feelings about the music might make you think you’re having strong feelings about the lead singer.
(More on the power of context here.)

7) And Most Importantly: Live An Interesting Life

Remember the theme of Don QuixoteIf you want to be a knight, act like a knight.
If you don’t read, watch and think about generic things, generic things are less likely to come out of your mouth.
This doesn’t need to be expensive or difficult. Hang out more often with the most interesting people you know.
The friends you spend time with dramatically affect your behavior — whether you like it or not.
The Longevity Project, which studied over 1000 people from youth to death had this to say:
The groups you associate with often determine the type of person you become.
In The Start-up of You, Reid Hoffman and Ben Casnocha talk about how the best way to improve particular qualities in yourself is to spend time with people who are already like that.
The best and most reliable way to appear interesting is to live an interesting life.
And to pursue that ends up being far more rewarding than merely making a good impression on others.