Initiating a conversation with someone is often one of the most challenging aspects of communication. While some people might find it easy to strike up a chat, others may struggle as if it were an insurmountable task. However, don’t worry—there are numerous strategies you can use to start an engaging conversation with anyone, along with specific tips tailored to certain individuals. Follow the steps below to give it a try.
Steps
Initiating the Conversation

Show genuine interest. You can turn a complete stranger into a friend simply by making them feel valued and respected for their thoughts. If the person feels like they’re talking to themselves, they’ll stop sharing immediately. Turn your body toward the speaker and maintain gentle eye contact. Give them enough personal space while showing that you’re fully engaged in listening.
- Make the person feel their thoughts matter. If they bring up a topic, ask relevant questions instead of steering the conversation toward your own interests.
- After learning their name, use it once or twice during the conversation.
- If the person speaks first, nod attentively to show you’re actively listening.

Ask questions naturally. Many engaging conversations start with questions, but you shouldn’t make the other person feel like they’re being interrogated at a police station. Avoid rapid-fire questions without providing feedback or engaging in genuine dialogue. Nothing is worse than feeling like you’re being interviewed. Asking too many questions will only make the other person uncomfortable and eager to end the conversation.
- If you realize you’re asking too many questions, lighten the mood with a joke. You could say, "Sorry—our interview ends here!" and smoothly transition to another topic.
- Ask about their hobbies or interests, not their deepest dreams or aspirations.
- Talk about something exciting. Avoid asking their opinion on the latest disaster news or whether they’ve been working overtime. Make them interested in the topic and the conversation itself.
- Ensure you share as well. Ideally, both of you should contribute equally to the conversation.

Be humorous. This doesn’t mean you have to do anything extraordinary—just sprinkle in a few jokes or share a funny story to break the ice. You’ll be surprised how humor can make people more open. Everyone loves to laugh, and laughter puts people at ease. It’s a great way to relax tense individuals and kickstart a conversation.
- Use wit to grab attention. Show that you’re quick-witted, enjoy wordplay, and love sharing jokes.
- If you have a favorite joke, share it—just keep it short. Avoid telling a long story you’ve never tested before, or it might fall flat.

Ask open-ended questions. Open-ended questions require detailed responses, not just yes or no answers. They allow the other person to share more, which is what makes a conversation flow. Using these questions draws the other person in and makes them an active participant. Open-ended questions help the conversation grow, unlike closed questions that limit responses.
- Ensure your questions are appropriately open. Don’t ask someone about the meaning of life; instead, ask their thoughts on the Vietnamese football team’s performance last season, for example.
- Recognize when the conversation isn’t going well. If someone only answers with yes or no to a question that should invite more detail, they might not be interested in talking.

Know what to avoid. Many factors can kill a conversation before it has a chance to flourish. If you want to start a quality conversation, steer clear of some basic pitfalls from the beginning.
- Avoid oversharing personal information. Don’t talk about your painful breakup, a strange rash on your back, or your confusion about whether someone truly loves you. Save these topics for someone close to you.
- Don’t ask questions that might make the other person uncomfortable. Let them talk about their loved ones, career, or health, but avoid asking if they’re dating anyone—they might have just gone through a breakup.
- Don’t talk only about yourself. While sharing interesting tidbits and some personal details can make the other person feel at ease, rambling on about how great you are or what you’ll eat tomorrow will quickly bore them.
- Stay focused. Don’t forget their name, job, or important details they’ve shared within minutes. This will make them feel unimportant. When they introduce themselves, repeat their name aloud to help remember it.
Starting Conversations in Different Situations

Start a conversation with someone you like. If you’ve just met someone you’re interested in and want to strike up a conversation, you need to grab their attention immediately by saying something unique, witty, engaging, and slightly flirtatious. When talking to someone you like, how you speak matters more than what you say. Maintain eye contact and face them, showing that you’re fully engaged. Here are some great ways to start a conversation:
- If you’re at a party, comment on the music playing. You’ll have something to discuss—whether you both love or hate the music doesn’t matter.
- If you meet them at a bar, ask for a drink recommendation. You can compliment their choice or playfully tease them if it doesn’t suit your taste.
- Talk about their hobbies. Don’t come on too strong—ask what they enjoy doing on weekends.
- Avoid talking about your job. It’s not the most exciting topic, and you can save it for later.
- Tease them lightly. If it’s hot outside and they’re wearing a sweater, gently joke about their fashion sense.
- Bring up pets. People love talking about their pets, and if you both have one, you can even share photos.

Start a conversation with someone who could become a friend. If you’ve just met someone you instantly want to befriend or are introduced to a friend’s friend and want to get to know them better, subtly show interest without making it feel like an interview. Make them laugh and want to learn more about you.
- Stay positive. Avoid self-deprecating remarks or complaints; start with something upbeat, like discussing a local sports team’s success (if they’re into sports) or your favorite bar or restaurant.
- Talk about where you live. People are often proud of their hometowns and what they enjoy doing there. If you live in the same area, you can bond over its highlights and later share more personal stories about where you’ve lived.
- Ask about their hobbies. You might discover shared interests.
- Don’t talk too much about yourself. Ensure the conversation is balanced, and you learn about them too.
- If you have mutual friends, ask how they know each other. You might hear funny stories about someone you both know.

Start a conversation with a coworker. Talking to a coworker can be trickier than chatting with someone you like or a potential friend, as workplace boundaries exist. However, staying positive and sharing just enough about your personal life can lead to enjoyable conversations.
- Ask about their family. Everyone loves talking about their family, so ask how theirs is doing. They might even show you photos and share more than you expect.
- Discuss weekend plans. If you work together, you’re both likely looking forward to Friday afternoon and relaxing over the weekend. They’ll happily share their plans if you don’t seem too nosy.
- Bond over shared annoyances. Complain about traffic, the broken photocopier, or the lack of cream in the kitchen—you’ll both laugh and start a fun conversation.
- Don’t focus too much on work. Unless you’re discussing work-related matters, show your personality and talk about friends, family, and hobbies instead of projects or reports. Build a connection beyond work.

Starting a conversation with a group of people. This can be even more challenging. The best way to initiate a conversation in this scenario is to find a common interest. While it’s difficult to make everyone feel comfortable and included, try to engage as many people as possible by keeping things open and lighthearted.
- Make fun of yourself. This is a great strategy, especially when starting a conversation with people who know you but not each other. Let others laugh or tease you, and gradually they’ll bond with one another.
- Aim to include everyone, not just one or two individuals. If you focus too much on one person, others might feel left out.
- Talking about things you dislike can also spark a conversation, as everyone dislikes something. Start by sharing a story about something that bothers you, and others will likely join in.
- Think about the group’s commonalities and bring them up. You don’t need to be subtle. For example, say something like, "Hey, you both are Arsenal fans, right—did you catch last night’s game?"
Tips
- Imagine a conversation as a seesaw. Both participants need to share equally, so avoid rambling about a boring topic to prevent making others uncomfortable. If the other person dominates the conversation, speak up. You’ll enjoy it more if you actively participate.
- Pay attention to your tone. Speak at a moderate volume—neither too soft nor too loud.
- Think about what you can say before starting a conversation. This will help you avoid dull exchanges.
- Don’t try to dominate the conversation; let others open up to you.
- Avoid yes-or-no questions. Instead, ask questions that require thought and elaboration.
Warnings
- When asking personal questions to someone who isn’t a close friend, avoid being too intrusive. Stick to questions like, 'What are your plans for the holiday?' 'What did you buy at the mall?' 'Where do you live?' or 'How’s your family doing?'
- Avoid topics that might make others uncomfortable or awkward, as they may become silent or hesitant.
