How to Start a Conversation with (Almost) Anyone

Have you ever spotted someone from across the room and felt immediately that you wanted to meet him, but wasn’t sure how? Humans are wired to connect and interact, but if you’re out of practice at striking up a conversation, it can seem quite daunting to make the first move!

The ability to start a conversation with a stranger is an incredibly helpful skill to have. Connecting with others injects richness and meaning into all aspects of our lives. There are so many places and ways to meet new people – at work, at a social gathering, while out running errands, traveling, or anywhere else life may take you. Just like anything, practice makes progress. The more you initiate contact, the easier it will get.

For example, I know of a woman who was on a flight for business. The man in the seat next to her, I’ll call him Joe, was friendly and introduced himself. My friend, I’ll call her Sarah, was apprehensive in her response. Finally, however, she gave in to the conversation (it was going to be a long flight anyway) and she learned that he practiced law in the same town that she lived in. Sarah was seeking representation for a legal business issue, and it turned out that Joe was just what she needed. They are still friends to this day.

It’s so easy to miss these opportunities, these gifts, to connect with others. Look at the people around you and you’ll notice many caught up in the microspheres of their personal lives, especially on smart phones, increasingly becoming disconnected from society.

While I was at the gym the other day, I noticed that all the men and women around me were sitting at workout machines lost in their phones! None of them were exercising anything other than their thumbs. It was a bizarre scene!

Well ladies, it’s time to buck the trend! Make a commitment today to start taking steps to connect with others who cross your path. You could make a new friend, book a new client, or meet your future significant other.

Just Two Requirements

For a conversation to start, two things must happen:

  1. You must conquer any reticence or fear you have to approach and talk to a stranger.
  2. The stranger needs to be receptive to speaking to someone they don’t know.

Since you are only in control of your own actions, don’t take it personally if the other person doesn’t eagerly engage. You don’t know their story or what they might be going through. If anything, they’ve missed out on a great opportunity to get to know you!

Start with Hello

Start exercising your communication muscles by saying hello to people as you walk by them on the street. Smile as you approach, look people in the eye and say your favorite greeting – hi, hello, hey, or how’s it going.

The goal isn’t to start a conversation. It’s to open yourself up to others, and let them know that you are receptive, confident, and comfortable with yourself. If you get a hello back, you’ll know you’ve passed by someone who is also confident, open, and comfortable. If she looks down and says nothing, don’t let it bother you. She may not be at ease with speaking to strangers, and chances are, she wasn’t the person you were meant to connect with anyway.

Make it a fun game! When you see someone walking with their head down, try and get them to look up at you and see your beautiful smile with just a simple and cheerful hello.

After you’ve done this enough, it will start to feel natural and effortless. Now you can build on the self-confidence that you are acquiring.

Time to Chat

It’s show time! The easiest way to get a friendly conversation going with someone new is to ask them about themselves. Most people love talking about themselves because it’s easy. It also shows that you are interested in them. They’re flattered!

Here’s What to Do:

  1. Identify the person you want to speak to. (For this illustration, we’ll use the pronouns “he,” “his” and “him.”)
  2. Approach him with a genuine smile and look him in the eyes.
  3. Take a breath and relax. The more relaxed you are, the more relaxed he will be. People pick up on our cues.
  4. Comment on what he is doing, compliment him in some way, or ask him a question about himself. No pick-up lines allowed and don’t worry about flirting. You can do this later. The point here is to put him at ease and encourage him to open up to you.
  5. If he engages with you, let the conversation flow naturally. If he doesn’t, move on with confidence – it isn’t you, it’s him.

Need some more guidance? Here are some possible scenarios:

Comment on an Object You Notice

Scenario 1: He is wearing a shirt with some kind of team, college, or brand name on it. Say, “Hi, I like your UCLA (or whatever is represented) t-shirt. Did you go to college there?”

This approach is great, as it can lead to an extensive conversation about where he is from, what he majored in, if he played sports, etc.

Scenario 2: He is wearing or carrying something that you can comment positively on. Say, “Hi. I’m always keeping an eye out for a gift to get my (brother/cousin/friend) for (his birthday/the holidays.) I really like your (shirt/jacket/coat/shoes/backpack.) If you don’t mind my asking, where did you get it?”

This question can lead to an interesting conversation about the person’s likes and dislikes, where he shops, where he is from and more.

Comment on What He’s Doing

Scenario 3: You’re in a bar. Your person of interest is watching a game on TV. Say, “Hi. Who are you rooting for? Are you a (name one of the teams that are playing in the game) fan?”

Talking about sports is a great way to initiate conversation. It often leads to finding out where he’s is from, what he likes to do and his sharing experiences he’s had as a fan.

Scenario 4: You see someone you would like to meet reading a book on the bus, on a park bench, or at a cafe. Say, “Hi. I’m just wondering how you like that book? I’m looking for a new book to read and love getting recommendations. You seem to really be into that one.”

If he is receptive, this can lead to a meaningful conversation about books, authors, media, movies and more.

No matter what happens after you make your initial comment, keep eye contact and a smile on your face; ask questions and answer any that are asked of you. Let the conversation flow naturally from there. It can be refreshing for people when they’re approached by someone who has a genuine interest in them!

If the person doesn’t engage, don’t sweat it. Or if the conversation quickly peters out, end it by saying something like, “It’s been really nice chatting with you. Enjoy the rest of your day.” Don’t get down, or be self-critical. It’s natural that we don’t connect with everybody. Remind yourself that you are confident, worthy, and it’s their loss that they didn’t engage. It’s all good!

By actively engaging with others, you are opening up a world of opportunity for yourself. You’re expanding your horizons, learning, and growing with each encounter. Way to go! One day, you may start a conversation with a stranger who becomes a new friend, or possibly, your new love.

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