The Best Conversation Starters

There are many conversation starters that work. In fact, I believe you can start a conversation with almost anything.

I recently started a conversation by asking a person if they know how to stop hiccups, because for some reason I had begun to hiccup. It all went naturally from there simply because I was curious, talkative and genuine.

However, the best conversation starters don’t just work, but they work incredibly well and no matter who the person you wanna talk with is, they will rarely fail you.

The best conversation starters are the ones you can rely one to start the conversation, engage the other person and make an impression, and they also making it easy to keep the chat going from there.

Based on my experience as a social confidence coach and a passionate about social dynamics, I concluded there are 4 qualities that the best conversation starters all have, and these 4 qualities are what makes them so great.

  1. They are personal. Forget about commenting about the weather and stuff like that. Go with conversation starters that relate to the other person. That way you get to learn something about that person, they’ll engage in the conversation more, and you’ll have more paths to take the conversation on from there.
  2. They’re not too personal. At the same time, it’s not the best idea to start a conversation with a person you don’t know by asking them something very personal, like “Do you have any insecurities?” That’s too forward and it has more chances to inhibit the other person rather than make them to open up.
  3. They reflect a genuine interest. Never ask or comment about anything you don’t really care about. Because if you don’t care about it, chances are you’re not gonna know how to keep the conversation going from there, or you’ll take it on a path that doesn’t really interest you.
  4. They are delivered with confidence. If you are self-assured when you start a conversation, you will make a good impression and suck the other person into the conversation. Confidence is like a magnet and it’s one of the best qualities you can convey to others from the get go.

That’s it. Not all conversation starters fit these criteria, but you can find many of them that do.

My advice is to go from here and come up with your own conversation starters based on these 4 criteria. It would be ineffective and condescending of me to actually tell you what conversation starters to use.

The best conversation starters vary based on your real interests. I will give you some examples though of conversation starters that I use and work really well, just for inspiration.

“How was your day/evening/weekend?” I love to ask people about this and learn about the things they’ve done recently. I try to relate what they say and also talk about the things I did, and the conversation moves on from there.

“What do you do?” I’m always interested in what a person does for a living and I often ask about this. In my experience, it’s an awesome conversation thread to go on with most people.

“That’s a nice shirt/suit/pair of glasses. Where did you get them?” Since I’m interested in style, I like to notice cool things in other people’s appearance and comment on them. It’s pretty easy for me from there to make the conversation take off.

As you can see, every conversation starter is a good match with my interests, and it’s also personal, but not too personal. This is the recipe I encourage you to follow.

Also, always keep in mind that when it comes to making conversation, the way you talk is often much more important that what you actually say. If you are confident and at ease, people will love talking with you and what you say becomes secondary.

If you lack conversation confidence, check out this presentation right now. It’s a presentation I created that shows you precisely where conversation confidence comes from and what are the steps to developing it. I’m sure you’ll find it very useful.

Equipped with the best conversation starters, you will stand out from the pack. You will find it easier to make conversation and astonish others. You will have that extra leverage that can make your social life infinitely better.

Small Talk Conversation Starters

Small talk is a common presence in social settings. Even the very best friendships, partnerships or relationships often start out with simple small talk, which then evolves into deeper conversation and connects individuals emotionally.

Small talk conversation starters play an important role here, because they get the dialogue going. Equipped with a good understanding of the art of making small talk and a few good small talk conversation starters, you can converse with anybody.

The 3 Traits of Small Talk Conversation Starters

Small talk conversation starters that work well, all share three key traits. Grasp these traits and you’ll find it easy to come up with your own small talk conversation starters and to adapt them to the context.

  1. They are not too intrusive. Small talk overall is not very intrusive. It’s light, social conversation. So it makes sense for the conversation starters you use to not be very intrusive either.
  2. They are authentic. Contrary to conventional wisdom, it’s not a good idea to use convo starters that take a conversation in a direction you’re not really interested in; even if it is just small talk.
  3. They are adapted. Don’t go running around with one conversation starter and use it to initiate small talk everywhere. Adapt your approach so it makes sense in the social context you’re in.

10 Conversation Starters for Small Talk

Myself and many of my coaching clients have tested numerous small talk conversation starters, and I’m going to share with you 10 of the best ones. Correlate these starters with your interests and the social context, and you can confidently rely on them.

1. “What do you think of this event/ party/ gathering?” – Simple and straightforward.

2. “Who do you know here?” – Also a good way to meet more people and make new friends.

3. “What field are you in?” – Works great at networking and business events.

4. “Have you ever been to this place before?” – Terrific starter if you like the location you’re at.

5. “That’s a nice watch. Where did you get it?” – Also works well for other accessories or clothing items.

6. “Tell me about yourself.” – A nice, broad request. It can really get the other person talking.

7. “Have you heard about (major and recent event)?” – A bit of talk about the latest news never hurts.

8. “Where are you from?” – An excellent conversation starter for events with people from multiple cities or countries.

9. “How is your day going?” – Kickoff the chat by getting the other person to share their day.

10. “What are you drinking?” – A particularly good one if you have an interest in drinks or drinking.

Use these simple and effective conversation starters when you’re making small talk, and you’ll get the conversational ball rolling.

I know that small talk may seem pointless, but it is a valuable part of social interactions, especially with new people. It’s a way to test the waters and to engage another person. Know how to make small talk and how to move beyond it, and you’ll actually enjoy it.

Using Context to Find Conversation Starters

When you want to find good conversation starters to use, one of the best places to start looking is the very context you’re in. Open your eyes and your mind, and you’ll discover all sorts of ways to start conversations provided by this context, whether it’s a party, a conference or a date.

The Power of Contextual Conversation Starters

I like to use conversation starters based on the context because I find them smooth and effective. They’re not personal and intrusive as “What do you do for a living?” but they’re also not impersonal and shallow as “What time is it?”

I also like contextual conversation starters because they’re adapted to the environment and thus, they make a lot of sense. When you’re using a contextual conversation starter, you’re not employing a memorized line robotically; you are using your head to come up with a good approach based on the context.

Where, Who and What

Using context to initiate conversations starts with noticing the context and asking yourself some questions about it. As you answer your own questions, you’ll also discover good conversation starters to employ.

Socializing and providing communication coaching, I discovered there are three key questions to ask yourself:

  1. Where? (The Location). Thus, you can come up with conversation starters such as: “What do you think of this club?”, “What is it like to work here?
  2. Who? (The People). Thus, you can come up with conversation starters such as: “What did you think of the speaker?”, “Who are you here with?”
  3. What? (The Event). Thus, you can come up with conversation starters such as: “What do you think of the party?”, “Have you been to similar conferences before?

Clutching On To the Details

Besides the general characteristics of the context (location, people and event) there are also specific details that can provide great conversation starters.

This is why I encourage you to be aware of what’s going on in your environment and notice the little details. As you do so, you’ll find opportunities to initiate conversations.

I often start conversations at events where there is a Swedish buffet while picking up some food at the buffet table, by making a honest comment about the food to the person next to me in line. If that person is eager to respond with a comment of their own, the conversation is on.

I recently kicked off a conversation on a train with the girl who sat next to me by commenting about the train conductor who seemed drunk to me and asking her opinion about this issue. We joked about it a bit, and the rest of our chat happened naturally from there.

Using context to find conversation starters is, in my view, a much finer art than simply choosing randomly a convo starter from your bag of tricks. It reflects much finer social calibration and it keeps you on your toes. For this reason, it is something I highly recommend you to master.

Funny Conversation Starters

I believe one of the most important qualities that good conversations have is that they’re fun. They pull you in through their joyful and positive aura. If you’re gonna have a fun conversation, you might as well start it in a funny way.

Not all conversations are proper to be initiated using funny conversation starters or any funny conversation starter; this does require calibration. Nevertheless, I find that people in general are much more hesitant to use funny conversation starters than it’s warranted.

The point is not to force yourself to be funny, but to permit yourself to be funny. This applies especially in the beginning of a conversation, when it’s less probable for this to happen.

20 Funny Conversation Starters

To help you kick off conversations in a humorous way, here are 20 funny conversation starters. For this round, I’ll only stick to question-type convo starters:

“How did you find out there is no Santa? You did find out, didn’t you?” (I often ask this; I really wanna know!)

1. “What do you think about laissez faire capitalism?”

2. “Do you know any good conversation starters?”

3. “What do you wanna be when you grow up? (Use it with adults)

4. “Are you a good girl/ nice guy or a bad girl/ bad boy?”

5. “What do you think about raising ostriches?”

6. “Do you have any food with you? I’m hungry!”

7. “Heard any good jokes lately?”

8. “Do you think good girls go to Heaven?”

9. “What do you think you were in a past life?”

10. “What was the last stupid thing you did?”

11. “What do you have a weak spot for?”

12. “What’s your opinion about black nails on men?”

13. “What did you wanna be when you were 5?”

14. “What’s your favorite color?”

15. “What’s the yuckiest food you ever tasted?

16. “What do you do when you’re home alone and the power goes out?” (I love this one!)

17. “If you could, what superhero would you want to be?”

18. “Read any scandalous news lately?”

19. “What’s the best present you’ve ever received?”

20. “Do you think they’ll make another Batman movie?”

In my view, initiating conversations in a funny, relaxed way is one of the most interesting people skills you can master. A conversation started with a laugh is a conversation with a lot of potential. Keep this in mind as encouragement to yourself to employ funny conversation starters.