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What Makes A Conversation Interesting?

Maybe right now you’re thinking of speaking to someone you’re attracted to. Maybe you even have a date planned. But you just want to make sure you don’t run out of good things to talk about.
That would be embarrassingly awkward, wouldn’t it?
Imagine both of you sitting near each other. There is a sudden pause in the conversation, and you know that you should say something now, but your brain seems to have stopped working. All you can think of is some boring question or stupid comment, but nothing interesting or good enough to actually say out loud.
You feel an awkward silence slowly descending like a dark cloud, and you start to panic inside. You feel like you’ve become a total idiot because your mind has become totally blank. It’s like you’ve lost your whole personality. You can barely even remember your own name at this point, let alone an appropriate thing to talk about.
You’re not alone if you’ve been in this situation before. I certainly have, many times. And I can understand that you want to prevent this from happening to you again, especially if you’re talking to a person who you like.
Well, good news! I’ve put together this cheat sheet of 50 interesting conversation topics you can use at any time to rekindle the conversation, even if you feel it start to go downhill. You can go over this list before a first date or a party, whenever you need to have a few good things to talk about in mind (just in case).
And don’t worry, almost all of the topics I suggest are “normal.” This means you won’t hear me tell you to say lines which a normal person would never talk about in real life.

 For example, many of the “conversation tips” articles you’ll find on the internet are embarrassingly cringe-worthy. They often give you silly suggestions like: “If you made a TV show about your life, what would you name it?” Who really says something like that? I know I wouldn’t.
So without further introduction, here is the list of topics that you can refer back to anytime. You’ll notice most of them are fairly straightforward and “ordinary.” That’s because you don’t need to be talking about aliens and obscure philosophy in most conversations. (Unless you want to!) Often simple and obvious topics are enough to kick-start your brain again.
I’ve also put them into groups to make it easier for you:

Hobbies



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If you find out what a person’s hobbies are, you instantly know a lot more about them. Hobbies are things people do without being paid to, just because they enjoy them. Some examples are: yoga, photography, working out, meditation, shopping, etc.

The best question I’ve found for finding out someone’s hobbies is:

  1. What do you do in your free time? Simple and effective. This also has the benefit of being an open ended question. If this doesn’t get you a great reply you can ask more specific questions like…
  2. Do you play any musical instruments?
  3. Do you draw, paint or do art?
  4. Do you like dancing?
  5. Talk about technology, gadgets, cars. (Best if you’re a guy talking to another guy. Yes this is a shameless stereotype, but I’ve yet to meet a girl who enjoys talking about computer specs with me — though I’m sure they exist!)

Work/School





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Some people say you shouldn’t talk about work. I think that’s ridiculous. When you stop and listen to what people usually talk about, work and school are at the top of the list.

After all, people do spend several hours a day at these places. And their work or school are often related to an area they’re very passionate about. Their coworkers are also some of the people they spend the most time interacting with.

However, be warned: for some people these topics can be boring. Older people may be sick of talking about their work, and other people may only be doing a boring job for the money, like a student cashier or construction worker.

  1. What do you do/study? (Yes, the simplest and most common way to start a conversation.)
  2. What is your most (or least) favorite subject in school?
  3. How do you get along with the people you work with? (People love talking about their relationship and frustrations with other people. Yes, it’s gossip, but you also learn a lot about how the person works this way.)
  4. Do you love working there or are you doing it for the money? (This can be a playful question on a date, not a good idea at a networking event.)
  5. What is your dream job? Another way to ask this: If money didn’t matter, what would you do with your time?


Travel



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Many of the most memorable experiences in people’s lives came from traveling. When you’re in an unfamiliar place, in the middle of a new and strange culture… that’s gonna make a big impact on you.

And even if someone hasn’t traveled a lot yet, they usually have dreams of traveling in the future. Either on vacations or later in retirement.

  1. What countries have you traveled to? (If you two have visited the same country, you may be able to talk about those shared experiences for hours.)
  2. What was your biggest experience of “culture shock” in another country?
  3. Where in the world would you love to live most? Why?
  4. How does your home country compare to here? (If they were born/raised in a different country.)
  5. What’s the worst thing that’s happened to you while traveling? (Be careful with this one, although you will get some interesting responses. I’ve heard people getting robbed by taxi drivers, getting scammed for a few bucks, etc.)
  6. Have you ever traveled by yourself? (Or you can ask would they?)
  7. Do you speak any other languages?



Entertainment



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Walk around in public, and you will always hear people talking about movies, TV shows and books. For some reason, people love talking about stories and the characters inside them they feel like they know. There’s always new ones coming out, so the topic never really gets stale.

  1. What’s your favorite movie (or TV show) ever?
  2. Which movie/book/show are you ashamed to admit you love? (Lots of people read books like Twilight or watch reality TV as a guilty pleasure.)
  3. Which movie are you most looking forward to being released?
  4. What kind of books do you usually read? What was the last one you read?(This question is great if you’re on a date and trying to find an intelligent person!)
  5. What kind of music are you into right now? (A study found talking about music preferences leads to a quicker connection because music reveals your values to others!)
  6. What concerts have you been to? (If someone spends the money and time to go see an artist live, it means they like them a lot.)
  7. What movies have you watched more than once? Or what books have you read multiple times? (I’ve watched the Breaking Bad TV show 3 times already because it’s my favorite.)
  8. Do you play video games? (When someone is REALLY into video games, it’s a large part of their daily life.)



Food/Cooking




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This is a light and fun topic.Everybody eats, and most people enjoy talking about their personal taste in food. If this is your first conversation with someone, then don’t try to figure out the meaning of life. Find out what type of food you should try!

  1. Talk about a recent restaurant you or they went to. How was it different than others, why was it good, why was it bad?
  2. What type of cooking do they do at home? Do they dislike it or find it relaxing?
  3. Do they usually cook food from a specific culture? (For example, maybe their parents are from Vietnam and that’s 90% of the food they eat.)
  4. Do they follow any specific diet? Like vegan or paleo for example. This can tell you A LOT about their personal values. (Don’t ask this to a fat person, they will probably get offended if they are sensitive about their weight.)

Past Experiences






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The challenge with talking about past experiences, is that you usually don’t want to get too personal too quickly. If you do, the conversation may start to sound like a therapy session.

On a romantic date some of these questions may be appropriate. In other situations you’ll want past stories to come up more spontaneously, as they relate to whatever topic is being talked about. For example, if the topic of some new music trend comes up, you can mention what type of music you were into as a kid.

  1. Where did you grow up?
  2. What were you like as a kid? (Behaved, rebellious, quiet, attention-seeking, etc.)
  3. What did you want to be when you grew up? (You can also turn this into a funny question by asking them “What do you want to be when you grow up?”… even if they’re an adult.)
  4. What were your past jobs like?
  5. Do you have any siblings?
  6. Find out if you two shared any common interests as kids. (Maybe you were both interested in Pokemon, Harry Potter, etc. This can be an amazing way to build a lot of rapport quickly.)

Present Observations



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This one is something most people miss… Back when I had a hard time carrying conversations, I’d oftendesperately try to think of new random topics to talk about out out of thin air. I would search my brain for something cool to say… like a magician pulling a rabbit out of his hat. As you can guess, this didn’t work that well.

What I’ve now realized is that making small observations about your environment is a great way to restart any conversation. Instead of racking the inside of your brain searching for something to say… instead try looking around you and pointing something out in the environment. This will often naturally lead to other things you two can discuss.

  1. If this is your first time meeting… Why are you both here now? If it’s an art gallery or a business networking event… that is the best topic to start the conversation with.
  2. Make a comment about something they’re wearing. Maybe it’s an interesting piece of jewellery or a compliment about their shirt.
  3. What other people are nearby? (Talk about what they’re doing, guess what their personality is like, maybe even make up a funny conspiracy story.)
  4. Is there anything new, unusual or different about your environment?
  5. Put more attention into your physical senses… Is there music playing? Some smell that you didn’t notice before? Are you eating something? What can you feel touching your skin?

Future Plans





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People love talking about what they are looking forward to. The challenge here is not to sound like a job interviewer with something like “Where do you see yourself in 5 years?”

  1. What are you doing this weekend? (Very common conversation topic. This is a great way to start a conversation with someone you already know.)
  2. What local events are you looking forward to? (This could be a festival, holiday, concert, protest, or anything.)
  3. Would you prefer to live in the city or on a farm?
  4. What’s your main goal right now? What are you trying to accomplish?

Human Relationships





Almost nothing is more fascinating to most people than talking about how people work. Why? Because much of the meaning in our lives come from our connections. And to get what you want in life, you have to know how to handle people.

  1. Talk about men or women. I’ve seen guys connect very quickly talking about women, what they do, and how they operate. And I’ve heard this is even more true when women talk to each other about men.
  2. Ask them what their friends are like? Are they very similar to each other, or opposites?
  3. Have they had with the same friends most of their life, or made a lot of new ones?
  4. Ask about their family. Who did they live with? Were they strict, or easy going?
  5. Talk about some interesting idea you know from psychology. If you read a lot of psychology books like I do, this is easy. You can tie it into a story they just said.
  6. What do you believe is true that most people would disagree with you on? (This is a bit of an unusual deeper question, but I’ll put it in here since it’s really powerful. In fact, one of the most influential investors in the world says this his top interview question.)


Conclusion



Whew! That’s a lot of topic suggestions!

I hope you’ve picked up at least a few that can help you in your next conversation. One last point in conclusion…

Comments

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