Master How to Start a Conversation and Keep It Flowing

Having trouble starting conversations, whether with strangers or people you already know? Getting more comfortable just takes practice—and a bit of guidance. To help you become a more confident speaker, Best Life turned to the experts for their top conversation tips. Read on to find out what questions to ask, whom to ask them to, and loads of other tricks for starting and keeping a conversation going. Whether you want to improve your social skills for personal or professional reasons, these insights will give you the tools to become a more self-assured conversationalist.

Why Is Knowing How to Start a Conversation Important?

A great conversation isn’t just about exchanging information—it’s about building the foundation for partnerships, friendships, or other opportunities. Good conversation skills are crucial for career growth, fostering workplace harmony, and turning casual chats into meaningful connections. Even dreaded “small talk” has its purpose, showing empathy and a willingness to listen, even if the topic seems dull.

It’s also important to remember that not everyone feels equally confident in conversations. “Everyone should know that while some people naturally enjoy chatting, no one is born a skilled conversationalist,” says Jodi RR Smith, president of Mannersmith Etiquette Consulting. “It takes time and practice.”

12 Tips on How to Initiate Conversations

1. Prepare some good conversation starters.

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Ever found yourself stuck in a social situation with no idea what to say? If so, it’s time to build an arsenal of conversation starters.

“Always be prepared to introduce yourself,” says Jodi RR Smith, president of Mannersmith Etiquette Consulting. “Just stating your name isn’t enough. Include a small piece of information about yourself. This little detail will help you start a conversation or give the other person something to ask you about.”

Keeping up with current events also helps. “Stay well informed,” advises Liza Grotts, certified etiquette expert and author of A Traveler’s Passport to Etiquette. “Read at least one daily newspaper, and don’t forget the sports section.”

2. Use open-ended questions.

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The benefits of using open-ended questions in conversation are clear. They encourage people to share more about their thoughts and experiences compared to close-ended questions. Additionally, they promote critical and creative thinking, leading to deeper conversations that explore different perspectives instead of merely exchanging information.

3. Ask them about their life.

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By showing genuine curiosity about someone’s passions or background, you not only keep the conversation going but also deepen your connection. Meaningful conversations aren’t about bombarding the other person with questions to fill the silence—you want to peel back the layers to uncover who they truly are, creating a space where they feel seen and heard.

“Asking others about themselves is essential for keeping the conversation fresh and ongoing,” says Randi Levin, a transitional life strategist and founder of Randi Levin Coaching. “We’ve all experienced talking to someone who only talks about themselves. Nothing is a bigger turn-off.”

4. Find common ground.

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Shared experiences and interests are catalysts for connection. They make conversations more pleasant and smoother. Levin says that shared experiences are a great way to start a conversation. When we find common ground, there is an implicit know, like and trust factor. Any common ground, whether it’s a shared hobby, professional background or dislike of Monday mornings can help facilitate a more meaningful dialogue.

If all else fails, there are always strategies like the FORD method. FORD stands for “family occupation recreation dreams.” You can find topics that resonate with both you and your partner by asking questions in these areas.

5. Throw in a compliment.

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Positive comments about someone can lighten the mood and make them feel valued. Levin reminds that the best compliments come from a genuine and heartfelt place and are woven in the conversation. “They should be more about the insights gained from talking to each other than about superficial appearances and surface fluff.”

It’s important to know when to cut back. “Sincere complements are lovely. Smith warns that being insincere can make people suspicious of you.

6. Maintain eye contact.

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Eye contact is a way for speakers to say, “I am here with you in this moment.” By maintaining this visual link, your conversation partner will feel acknowledged and appreciated. A steady gaze without staring can convey confidence and sincerity. This builds trust during the conversation.

7. Pay attention to body language.

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The way we stand and the gestures we use, as well as the distance we maintain, can either compliment or contradict what we say aloud. Smith says that your body should be facing the other person with shoulders squared to each other and an open body posture. “Make sure that your arms aren’t crossed and your hands aren’t hidden in your pockets,” says Smith. You don’t want your relationship to become too close too quickly. Be sure to keep an eye on the other person’s reaction and give them some personal space.

8. Ask for their opinion.

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Asking for someone’s opinion shows that you value their thoughts and perspectives. It encourages them to share more about themselves. “Connection is about learning. Conversation is the road to that connection, so asking for the opinion of others is a key way to build upon communication and engage in learning something new,” says Levin.

Requesting input also opens up new avenues for discussion, making the conversation more dynamic and engaging. Moreover, it can help uncover common interests or differing viewpoints, both of which can lead to deeper and more meaningful exchanges.

9. Crack a joke.

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Making jokes creates bonds by establishing a shared sense of humour and lightening the mood. It can also serve as a bridge to more serious topics. However, it’s important to proceed with caution when using humour.

“Humour is great when used appropriately in a discussion, but not if it is used as a substitute for good communication because one person feels insecure,” says Levin. “It’s okay to make a joke sparingly that fits the context of the conversation and emphasises a point, but it should be a one-off, not a continuous routine.”

10. Wear something worth talking about.

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A unique accessory or striking outfit naturally draws attention and curiosity, prompting others to comment on or ask about it. It can also raise a variety of topics, from fashion preferences to personal stories behind the item. “Entering a room or entering a conversation with something interesting that is a visual conversation starter is a fun way to break the ice,” says Levin.

Of course, you don’t want to overdo it. Make sure what you’re wearing is appropriate for the event, and don’t spend too much time talking about your wardrobe. It should be utilized as a conversation starter, not the conversation itself.

11. Offer to help with something.

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Offering to help shows that you are genuinely interested in someone’s needs and are willing to invest some time to assist them. Working together on a common goal can also foster a sense of camaraderie.

“There is no better conversation booster than feeling like we are being heard and appreciated by someone else,” says Levin. “Offering to help with an event, or a connection, or with a project indicates that we value the potential relationship that our conversation has begun, and we see value in continuing it.”

12. Ask follow-up questions.

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By asking for clarification or further details, we show the speaker that we are listening actively while encouraging them to explore their thoughts more fully. It says, “I’m engaged in this conversation, and I want to understand more.”

This approach is particularly effective in in-person conversations, where non-verbal cues can further enhance the exchange. Some examples include:

  • Can you give me an example of what you mean?
  • How did that make you feel?
  • What was your thought process behind that decision?
  • Can you explain that in more detail?
  • What do you think the implications of that are?

13. Keep practicing.

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practised,” insists Smith. “Whether it’s with the cashier at the local shop, the librarian, a fellow commuter, or someone waiting in line, try having a brief conversation about the weather or current events. The more you practise, the more comfortable you’ll feel, and the better you’ll become at small talk.”

She reminds us that this advice doesn’t apply in situations where we feel too awkward or afraid. “Manners matter, but safety comes first. Don’t strike up conversations with strangers when you’re alone, at night, or in a potentially dangerous situation,” Smith warns.

Things to Avoid When Starting a Conversation

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If you want to get better at having conversations, it’s just as important to know what not to do. Here are some tips on what to avoid when you’re chatting with someone:

Avoid Touchy Subjects

When you’re having a casual conversation, it’s best to stay away from politics, religion, and other controversial topics. These subjects can quickly turn a friendly chat into a heated argument. Stick to safe, neutral topics that everyone can enjoy.

Don’t Dominate the Conversation

Think of a conversation like a game of catch. You toss the ball, hold it for a bit, then throw it back. If you’re doing all the talking or none at all, something’s off. “Good conversations are all about balance,” says Smith. “If you find yourself dominating the conversation or not contributing, it’s time to adjust.”

While it’s great to share your own stories, constantly steering the conversation back to yourself can seem self-centred. Make sure you’re showing genuine interest in what the other person is saying too.

Don’t Get Too Personal Too Quickly

Respecting boundaries is crucial. Don’t dive into deeply personal or intrusive topics, especially at the start. Building a good rapport takes time. “This isn’t an interrogation,” Smith says. “Don’t ask overly personal questions right away. And be aware of power dynamics—someone might feel pressured to answer just because of your position.”

Keep It Positive

Try to keep the conversation light and upbeat. Complaining or focusing on negative topics can bring everyone down. Instead, talk about positive experiences and subjects. This keeps the chat enjoyable and leaves a good impression.

Know When to End the Conversation

It’s important to know when to wrap things up. “Talk long enough to be polite, but don’t let a quick chat drag on forever,” advises Grotts. “When it’s time to go, a simple ‘Please excuse me,’ or ‘It was nice talking with you,’ works fine. No need for a lengthy explanation.” Remember the three Bs: “Begin. Be brief. Be gone.”

Common Conversation Roadblocks

Woman is frowning and looking away from her boyfriend with her arms crossed, as he is looking worriedly into her face as they stand at home in their lounge
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Even the most experienced conversators can experience moments of discomfort or uncertainty that can hinder the flow of dialogue. These obstacles are not dead-ends; they are just detours which require a little navigational knowledge to overcome.

How do you handle award silences?

The name comes from the fact that awkward silences are unpleasant to experience. Although they can be difficult to escape, they don’t need to stop the conversation. Use compliments or interesting questions to fill in these gaps and keep the discussion flowing. A funny story or anecdote can also be a great way to lighten the mood.

Change topics gracefully.

It is important to change topics gracefully. It’s all about knowing when a topic has run its course, and finding a new angle to keep the conversation going. If you’re wrapping a discussion on a recent vacation up, you could segue into another topic by asking about future travel plans and favorite destinations. This method shows that you are genuinely interested in your conversation partner’s opinions and experiences.

Managing social Anxiety.

Anxiety is a warning signal that something is wrong during social interactions. If you are anxious in social situations, prepare in advance and practice in low-pressure scenarios. You can also use calming techniques such as deep breathing or taking a moment to yourself.

About Tips Clear

Tips Clear is a seasoned writer and digital marketing expert with over a decade of experience in creating high-quality, engaging content for a diverse audience. He specializes in blogging, SEO, and digital marketing strategies, and has a deep understanding of the latest trends and technologies. Tips Clear's work has been featured on various prominent platforms, and he is committed to providing valuable insights and practical tips to help readers navigate the digital landscape.

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