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How to Start a Conversation

Master the Art of Starting Conversations: 10 Proven Tips to Help You Succeed

How to Start a Conversation

Have you ever been at a party where you’re trying to make small talk with someone new and you meet someone who just stands there silently, not saying a word? Or maybe you met someone who just keeps talking and talking about themselves without giving you a chance to say a word, forcing you to search for an opportunity, any opportunity, to run for the hills?

I know I have. It can be uncomfortable and not really engaging. But don’t worry, it’s not as hard as it seems. The key to starting a great conversation is not trying to be interesting, but being interested in the other person.

Here are 10 practical tips to help you start a conversation that will make the other person comfortable and engaged.

Ways to Start an Engaging Conversation

#1. Give a compliment

Who doesn’t like to hear a genuine compliment? And you don’t have to go over the top, just observe something you like and mention it. Being complimentary can be a great way to get the conversation flowing.

Here are some examples:

  • “I saw you’re driving a Pinto, that’s such an underrated car!”
  • “That’s a sharp shirt, the color looks great on you.”
  • “I liked your presentation, you made it easy to understand”

But be mindful, avoid physical compliments if you can, especially if it’s not something that’s obvious, like a new haircut. It could be interpreted as weird or creepy.

Remember, paying a sincere compliment can be a great conversation starter and a way to establish a connection with someone new.

#2. Ask an opinion

Asking for someone’s opinion is a great way to show them that you value their thoughts and that you’re interested in what they have to say.

Here are some examples:

  • “I am thinking about trying this new restaurant, have you heard about it? what do you think about it?”
  • “What do you think about this new movie everyone is talking about?”

Be aware that it’s better to stick to topics that are relevant to the situation or the people you’re talking to. It might be odd to ask someone “What’s your opinion about the latest fashion trends” if you’re at a technical conference. Also, avoid asking too personal or controversial subjects that might lead to an uncomfortable conversation.

#3. Acknowledge shared experiences in difficult situations

When things aren’t going smoothly, acknowledging a shared experience can help create a connection and start a conversation. You might already be using this approach without even realizing it! For example, when you’re waiting in a long line at the store, you might comment to the person next to you about how the lines always seem to be the longest when you’re in a hurry. This simple observation can easily lead to small talk and a more in-depth conversation later on.

This technique can also be effective in more formal or high-stakes situations such as networking events, where everyone is trying to make a good impression.

For example:

  • “Networking events can be a bit intimidating, right?”
  • “I don’t know about you, but I always find these conference calls a bit tedious.”

However, it’s important to be cautious with this technique and to remain neutral when making observations. Avoid negative comments that may offend the person you’re talking to.

#4. Offer help

Offering help is a great way to show you’re friendly and approachable. It’s also a great way to start a conversation and build a connection with someone. If you find yourself in a situation where you can lend a hand, don’t hesitate to do so.

Here are some examples:

  • “I noticed you looking at the map, I’m from here, need any help?”
  • “It looks like those bags are a bit heavy, can I help you carry something?”

By offering your help, you demonstrate that you’re willing to go the extra mile to make someone’s day a little easier and it’s likely that the person will appreciate it and feel more comfortable and open to having a conversation with you.

#5. Ask for help

Asking for help is another effective way to build connections with others. It allows the other person to feel useful and valued, and it opens the door for a conversation and a deeper connection.

Here are some examples:

  • “I’m new here, could you help me find the registration desk?”
  • “I’m trying to fix my bike, any chance you know how to fix a flat tire?”

Asking for help is a great way to break the ice, show vulnerability, and build trust.

#6. Ask for information

By inquiring about a topic of interest or asking for advice, you demonstrate that you value the other person’s expertise and experience. This can open the door for a conversation and the opportunity to build a deeper connection.

Here are some examples:

  • “I’m planning to visit New York City next month, do you have any recommendations on things to do or see?”
  • “I’m thinking of taking a class on XYZ, do you have any experience or information about it?”

Asking for information not only allows you to learn something new, but also creates an opportunity to connect with others

#7. Look for common ground

One effective way to start a conversation is by bringing up common experiences or backgrounds. This approach is especially useful in situations where you know that you share something in common with the people around you, such as attending the same school, working in the same industry, or having a similar hobby.

Here are some examples:

  • “Are you an alumni from this university?”
  • “I see you’re wearing a marathon t-shirt, have you run one before? Which one?”

When you find and bring up commonalities, you instantly create a connection, which can lead to more topics of conversation and deeper connections.

#8 Ask about them

People generally enjoy talking about themselves, their interests, their family, and their experiences. One effective way to start a conversation and build connections with others is by asking questions and showing an interest in their lives.

Here are some examples:

  • “I see you’re wearing a pin of your favorite sports team, how long have you been a fan?”
  • “I heard you recently changed jobs, how’s the new role going?”

By asking about others and showing genuine interest in their lives, you demonstrate that you value them as a person; everyone loves that.

#9. Introduce yourself

When meeting someone new, it’s always great to have a casual conversation and get to know each other a bit by being straightforward and friendly. There’s no better way to do that than by introducing yourself and asking a question, even if it’s just for their name.

  • “Hey, what’s your name? I’m [Your Name], nice to meet you!”
  • “Hey, I’m [Your Name] and I love the tacos here. You?”

Just keep it chill and remember that you’re just trying to make a new friend or a connection.

#10. Make a joke about the situation

Sometimes a joke can help break the ice or make an awkward situation more comfortable.

  • “Well, this is a boring meeting, I guess we can all agree on that. But at least we’re getting a free lunch right?”
  • “If this meeting gets any more exciting, we might have to charge admission. Am I right? Hahaha. <sigh>”

Keep in mind that humor can be subjective and it’s important to be respectful and inclusive when telling a joke. Also, not all situations are appropriate for a joke, so use your discretion and good judgment.

Conversation Starter Tips

Body language is key

Make sure to use open body language, smile, and make eye contact. But if you notice the person is unavailable or uninterested in talking, respect their space and move on.

Listen actively

When you’re talking to someone, pay attention and actively listen to them. It’ll allow you to fully understand the information being exchanged, respond thoughtfully and build trust with the person you’re talking to.

Confidence is crucial

Starting a conversation can be intimidating, but remember the person you’re talking to is likely appreciative of the gesture. Don’t be afraid to approach someone new, even if it makes you a little nervous. The benefits of expanding your network are worth it.

Make connections

If your conversation goes well, exchange contact information. Follow up by sending an email, it’ll show them you enjoyed talking to them and want to keep in touch. Use specific details from your conversation as a reference to show you paid attention and valued the connection.


Starting a conversation can be a great way to make new connections and build relationships. By using open body language, actively listening, and showing confidence, you can make a great first impression and keep the conversation flowing. It’s also important to be aware of cues that the other person may not be interested in continuing the conversation, and in that case, it’s best to respect their space and move on.

Remember, you don’t want to be “that” guy who keeps talking even when the other person has clearly lost interest. Keep all the above tips in mind and you’ll be able to make great connections with ease. Good luck!

You might also be interested in learning about how to properly end an email or how to respond to interview requests.

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