How to Start Fantastic Conversations With Anyone

Do you ever…

  • Feel awkward or fearful about approaching people to start conversations?
  • Not know what to say when you’re chatting with someone and think they will judge you if you say something wrong?
  • Not know how to break into group conversations?
  • Feel uncomfortable or have social anxiety when you are out among acquaintances or people you don’t know?

Don’t worry. We’ve all been there. Building highly successful and effective relationships and collaborations with others is extremely hard to do. And it’s not an innate skill we are born with; relationship building requires learning new behaviors, skills, and habits. Today, we are going to discuss how to start conversations and make them successful!

Let’s start off with a few easy conversation starters:

  • “Happy Friday, how’s your week going?”
  • (If you have a beverage) “Cheers! What’s going on?”

Alternatively, you can ask:

  • “How’s your night going?” or “What’s happening?” or “What’s on your agenda for the weekend?” or “What did you do this week (or weekend)?”

And you never want to forget:

  • “How’s everything?”

If you’re at an event:

  • “What brings you here tonight?” or “How are you involved with this organization?”

A great catchall phrase to use:

  • “That’s fantastic. Tell me more…”

Asking questions will get people talking, and people love to share their experiences. People also love to share their opinions. Many people don’t have anyone who truly listens to them, so if you are that person, that can help build rapport quickly. Often, our best listeners are our closest friends. So by listening, you are acting like a person’s close friend, and someone is likely to think of you like that, which is another reason why this is a powerful tool for rapport building.

Here are some good opinion questions:

  • “Hey, do you know any great restaurants around here?”
  • “Where do you like to go out in the city?” or “Have you been to any new hot spots in the city lately?”
  • “Do you know any great organizations I should check out?”
  • “What upcoming events are you excited about?”
  • Or just, “What do you think about…”

You put that person in the position to be an expert, and you value you them enough to ask for their opinion. Plus, you are actually listening to them versus talking. Most people talk significantly more than they listen because they are trying to “sell” themselves and get validation or approval from someone else. Validate and approve yourself and you move past a major obstacle so many people get caught up in.

Also, it is powerful when you give people positive feedback, praise, or a compliment, but only when it is genuine. If you find out someone got a new job, congratulate them. If you hang out with someone often and they make you laugh, tell them. If you run into someone and they are wearing something striking, mention it. If someone makes a good suggestion or idea, tell them. The key here is to be genuine and specific about the comment you are about to make.

Here is what a typical conversation might look like:

  • “How’s your week going?”
  • Let’s say they mention they went to a concert. “That sounds like a lot of fun. Tell me more. Are you a big music fan?” You could follow up with any of the following: “What are your favorite bands?” “Where do you like to see bands?” “Do you play an instrument?”
  • Interject some commentary about what they are saying, and also if you have an opinion on music. Don’t try to impress someone or lie. Just be yourself and add to the conversation.
  • Also, point out any commonalities you have with someone else. It’s good to try to establish things in common to build rapport. You don’t have to go overboard here or try too hard. If something comes up that is genuine, point it out.
  • Then end the conversation by exchanging contact information (we will cover this later) and/or just say, “It was great to meet you, I have a few other people I need to speak with.” Or “I need to join my friends, why don’t you come over here and meet them.” Or “I am getting a drink, would you like anything?” Then you can go get them a drink, bring it back, and move on.

A conversation is simple: start it, engage the other person and build rapport, keep it going for few minutes, and then leave them thinking you are great person that they want to get to know better. It really just boils down to that.

What about approaching groups of people? These openers work well:

  • “What occasion are you all celebrating tonight?”
  • “What brings you all together today?”
  • You can also just use the openers we discussed earlier, and when you ask them what they are doing for the week or weekend, they will mention the group activity.
  • If you find out it is a bachelorette party, you can say, “I’m the entertainment for the evening!” Don’t be afraid to show a little humor.

And always focus on listening to and helping the other person first!


Bantering is a fun but powerful way to have conversations with people. It is using humor in a positive way to help people escape. And it’s a great way to flirt and create sexual tension as well. You can also use this in a business or networking setting, though you will need to tone it down.

Why does this work so well? When you tease a woman or a man and you’re willing to take risks in conversation, it shows that you have NO FEAR.

For men, being Mr. Nice Guy keeps the conversation safe, but it also spells major fear of rejection. Women are very perceptive, and they don’t usually respond too well to this. But when you boldly tease a woman and make conversation fun for her, you actively demonstrate you don’t have FEAR. You’re not concerned about saying the wrong thing.

More importantly, you’re not broadcasting your fear of LOSING her, before you’ve even ATTRACTED her. Bantering works on men as well, so women, it’s time to chat it up!

There are two basic ways to engage in friendly banter:

  1. The first is a form of a question based on selective hearing. “Did you just ask me…?” It doesn’t matter what someone says; interject to lead to the outcome you want. “Did you just ask for my phone number?”
  2. The next is a statement. It doesn’t matter what someone says, it is about what you believe they said. “If you wanted my phone number, you should have just asked for it.” “If you wanted to talk to me, you should have approached me a long time ago. I don’t bite!”

Other examples:

  • If you’re with a buddy and someone asks, “How do you two know each other?” Your response: Prison. They may say,
  • “How do you really know each other?” You can then tell the real story of how you met, but say the prison story is much funnier to tell.
  • “Did you just ask to buy me champagne?”
    If someone asks you how you are doing, you can say, “I’m feeling rather sexy (or awesome).”

Banter works much better when you do inner work regularly to gain more self-confidence and create a better vibe. I also recommend practicing banter with your friends and people you see often (i.e., with the barista at Starbucks, a hotel clerk, etc.) before you use it on strangers. Also remember to be respectful of others and not a jerk. Finally, if someone isn’t playing along with your banter, just say you were joking around, and drop it immediately.

Now you have a blueprint to start conversations anywhere, anytime with anyone. Start practicing every single day and you will make quick progress and have a lot of fun along the way!

Source: InspirationFeed

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