A Fool-Proof Guide to Starting & Keeping a Conversation Going

Last Updated: October 26, 2022

So, you're sitting in a room with someone else. Maybe you know them. Maybe you don't. Either way, the silence is deafening. But how do you start a conversation? Do you begin with "hi," a compliment, or a random remark? We know making conversation can seem complex, but it's actually easier than you may think! With our help, you'll be able to start and keep a conversation going with just about anyone (not to mention learn a valuable life skill). All you need are a few general tips, some examples, and a bit of confidence.

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Smart Conversation Strategies

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Be an active listener. Many people don't realize how important listening and paying attention are to being a conversationalist.^{[1]
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Expert Source

Maria Avgitidis
Matchmaker & Dating Expert
Expert Interview. 20 December 2019.} In fact, this is perhaps the most important thing you can do to be good at making conversation. Practicing "active listening" requires you to do two basic things:^{[2]
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Research source}
- Concentrate on what the speaker is saying. This is mainly a mental action — rather than just "hearing" what is being said, you want to get in the habit of thinking about what the speaker is saying as they say it. This sort of concentration can be mentally fatiguing at first, but it gets easier with practice.
- Show that you are listening. This is mainly a collection of physical actions. Look at the speaker to show your attention. Nod when you understand what they're saying. Say "uh huh" occasionally to show your agreement. Ask relevant questions.
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Be an instigator. It's hard to be a good conversationalist if you only wait for other people to come talk to you. Having the confidence to get out of your comfort zone and start conversations with others will improve your conversational ability immensely.^{[3]
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Expert Source

Maria Avgitidis
Matchmaker & Dating Expert
Expert Interview. 20 December 2019.} Begin by instigating conversations with people you already know. Even something as simple as "How is your day going?" can get a conversation started.
- Once you feel able to carry on a conversation with friends and family members, you can start going to places designed for meeting others: bars, clubs, large-group events (like parties or large-scale meetups), etc.
- All you have to do to start to start a conversation with a stranger is to say, "Hi, my name's [x]! What's yours?" You can also start with a talking point, like, "Wow, that's a cool shirt! Where did you get it?" or "Oh cool, you like [band/show/book/something visible on this person's clothing], too?"
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Make things about the other person. Everyone has interests. Once your conversation is underway, you can keep it going by asking about things you know the other person is interested in. If you don't know what the other person's interests are, just ask!^{[4]
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Expert Source

Maria Avgitidis
Matchmaker & Dating Expert
Expert Interview. 20 December 2019.} Comment on them with a few appropriate followup questions (e.g., "How did you get into that?").
- If you ask someone whether they're interested in something on their clothing and get an answer like, "No, it was a gift" or "It just looked cool," you're not out of luck. Try explaining how you know about the thing on their clothes and why you like it.
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Imitate conversations you hear. Good conversationalists learn from the best. To get exposure to people who are expert talkers, listen to podcasts, find an informative talk show you enjoy, or even participate in a chat forum (this is more reading than speaking, but the skills can cross-apply).
- Try to pay attention to the dynamics of multi-person conversations. Notice when speakers change: usually, this is during a pause or after someone has finished a sentence, thought, or argument. You can often detect when someone's ready to let others talk via tone. Listen for a note of finality at the ends of sentences, then pay attention to whether or not someone else chimes in.
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Try to end the conversation before you are forced to. The way a conversation ends is important — it's the very last thing that happens, so people tend to remember it well. A good rule of thumb is to end the conversation quickly and politely as soon as you feel even a hint of awkwardness (or even before this). Simply explain that you need to do something else — anything from "I'm going to get a drink" to "I have to go" to "I need to go take care of something" works well.
- If you feel that the conversation went well, this is your chance to set things up for another conversation with the person. Try saying something to the effect of, "Hey, I have to go, but I'd love to keep chatting later. What's your number?"
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Practice. You can't get better at making conversation without actually doing it. Try going to social events and talking to people you don't know. One-off events are best for starting out — there's no pressure of seeing anyone again if you mess up. Weekly or monthly groups are especially helpful once you start getting more comfortable. Repeated interactions are how friendships are formed and maintained.
- Once you make some new friends, paying attention during conversations is still important. Focus on the skills you're learning. Everything from recognizing speech patterns and mannerisms to picking up on conversation flow to commenting on important topics that come up can help you maintain your friendly connections as well as give you more experience.

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Navigating an Average Conversation

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Start your conversation. To start your conversation, all you need to do is say something like "Hi, how are you?" This gives you an opening statement and a question for your partner to respond to. It gets you past the awkwardness that can develop when each person is waiting for the other to talk and lets you jump right in to the conversation.
- Be ready — once you start, there's a good chance your partner will ask you a few pleasantries about how you are doing.
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Broach some easy topics of discussion. Having one or two questions ready beforehand helps here. This way, you won't need to waste time during your conversation to think about them. Try to pick topics that your partner will be interested in and able to comment on. If it's obvious that they have a certain interest, ask about this. If not, you can simply comment on whatever you're both doing at the moment and ask for input.
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Keep the conversation going. As the conversation progresses, continue commenting on the things that are being talked about during pauses and ask for your partner's input. As you continue the conversation, you learn more about the person you're talking with. This will make it easier over time to have conversations that feel natural and can give you some opening topics next time you talk.
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Try to avoid awkward silence. If you sense awkward silence coming, change the topic or end the conversation. By avoiding the silence in the first place, you are avoiding the common problem of rambling to try to bring the silence to an end. If you do find yourself in this situation, calm down and simply ask them about something "easy" like their family, a movie that's out right now, or the area where they live. These sorts of topics can "rescue" you from awkwardness.
- If things do get awkward, remember that you can always simply leave!

Expert Q&A

Question

How do I talk to my crush?

Maria Avgitidis
Matchmaker & Dating Expert
Maria Avgitidis is the CEO & Matchmaker of Agape Match, a matchmaking service based out of New York City. For over a decade, she has successfully combined four generations of family matchmaking tradition with modern relationship psychology and search techniques to ensure her professional clientele are introduced to their ultimate match. Maria and Agape Match have been featured in The New York Times, The Financial Times, Fast Company, CNN, Esquire, Elle, Reuters, Vice, and Thrillist.

Maria Avgitidis

Matchmaker & Dating Expert

Expert Answer

Social commentary on the environment you are in can be a really easy way to break the ice. Try talking about your school or office or the social event you are both attending. You should also consider asking them questions, like how they plan to spend the summer or what their plans are for the weekend.
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What if it is via online chat?

Community Answer

You should be approachable and likable, but you can talk about the same topics that you would talk about in person.
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What if I want her to be interested in me? What do I say?

Community Answer

Try to find common interests. Ask her simple questions to get to know her better. People like to talk about themselves, so just ask her hobbies, her family, what she does on the weekends, etc.