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10 tips for starting casual conversations that are worth having

Sites like Omegle and Chatroulette are known to connect you with strangers when you want to chat with someone. No one. Often these conversations are weird, but what if you want to take casual conversations to the next level?

This article lists some tips for starting better casual conversations that are worthwhile. Be it Omegle or other similar sites.

1. Use the right service

Emerald Chat

You can find a lot of random chat sites online, and many are quite similar. Most offer either video or text chat, others offer both. If you’re unhappy with the results of big players like Omegle, try some lesser-known options like Chat42 or Emerald Chat. There is also Wusoup, which is based on filtering creepy and low-quality accounts.

If the conversations are about you, try another service, like Talk.chat, which provides occasional group discussions. Meanwhile, through y99 offers several chat rooms grouped under different topics.

Our advice on starting occasional online conversations should be about the services you use.

2. Decide on text or video chats

Before you start chatting, you also need to decide if you want to use text-only chat or connect your webcam and microphone to video and audio chats. Both have advantages and disadvantages.

Text chat is better if you don’t want to show yourself to strangers. You can also take a minute to get answers instead of having to talk in real time. However, it is also easy to be lazy in text chats. You get a lot of “ASL?” messages to start the conversation, and nothing interesting was said afterwards.

Video chat, on the other hand, lets you put a face to the person you’re talking to. If you’re both involved, it’s a much more rewarding experience. The biggest drawback of video chats, of course, is that many people use their webcams for inappropriate purposes. If you don’t want people to do this, stay in the text message.

3. Ask interesting questions

Life Objective Discussion

It’s too easy to get into the same routine of asking how someone’s day has gone, what they’re doing for a living, and similar boring questions. To get more out of casual conversations, try asking deeper questions that get more interesting answers.

This may seem a little awkward at first, but if people are interested, you will have much more personal conversations. Some example questions are:

  • If you could invite anyone to dinner around the world, who would it be?
  • What is your life goal right now?
  • What is the most difficult event you have ever experienced?
  • If you could change one event in history, what would it be?
  • What is your greatest remorse?
  • What is your favorite smell and why?
  • How is your relationship with your family?
  • When was the last time you embarrassed yourself?

If you need more ideas, use a list like 36 questions which supposedly can lead anyone to fall in love. You can skip the romance focus, but there are a lot of great conversation starters here.

4. Try talking to people in other areas

If you use popular sites in your country, you’re probably only chatting with people in your area. The same goes for chat time – if you’re online at a normal time in your area, you’re likely to come across people living nearby.

You can confuse this by trying other chat sites like Chatroulette






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which serves different regions of the world. You can also try visiting chat sites on small mornings or other weird times when people around the world are more likely to be online.

Talking about people from other countries gives you more opportunities to ask about life around the world. Try this if your usual routine doesn’t produce interesting people.

5. Bring a friend

Most casual chat services do not allow you to invite people to text or video chats. Nonetheless, the physical involvement of friends in conversations can make the experience more enjoyable. Of course, this makes the most sense in video chats.

When there are two (or more) people in the camera, you wouldn’t feel the conversation is the best conversation. You can bounce topics from your friends when you’re not sure what to say. When the other person realizes that you are not alone, the conversation should be more cordial.

And when you come across strangers, you can laugh at them with your friends instead of sneaking on them. It’s a fun activity when you’re together and you’re not sure what else to do.

6. Keep track of the people you have spoken to

Put the pin in the world

If you often chat online, why not make a small project out of your experiences? After talking to someone a little, ask them where they live (usually). After a while, you can purchase a map to sign up where the people you’ve met online are coming from.

One particularly fun option is buy a drain map, either from your country / continent or from around the world. Otherwise, you can use pins to mark locations on a regular map. And if you don’t like the map idea, maybe you could set up a blog describing the different home addresses you’ve found?



Scratch the World Map poster


Scratch the World Map poster

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This will help you get to know your online chats over time.

7. Play a role

Mask mask

Are you tired of using yourself all the time? So why not try to pretend to be someone else from time to time?

Instead of reacting as you would like, try to act like a movie character or a famous character. See if another person can pick up your performance.

Of course, this strategy may not help you get to know people, and you should never do anything to make people feel uncomfortable. However, if you are trying to talk to yourself, it can be a good way to adapt to the process.

8. Filter out garbage

The right conversation Omegle

Chances are you’ll come across all sorts of spam accounts and people asking about inappropriate topics when you’re looking for random conversations online. Don’t waste time on these. If someone starts to be creepy, sends you automated links, or looks like a robot, just disconnect and move on to the next person.

You can also make clear what you are looking for from the beginning. When someone connects, you can attach a message like “I’m looking for a real conversation, so disconnect now if you’re not here.” While this sounds a little harsh, it makes your time more efficient by pruning people you wouldn’t want to talk to.

9. Import media

Are you trying to come up with a topic for discussion? Try media from elsewhere to generate ideas to talk about. You can share a YouTube video, a playlist of music, a fun meme, or anything else you’ve recently met online.

Likewise, if a site lets you define your point of interest, add a few so people know what you want to talk about. Most people enjoy finding new content and conversations for common interests, so it gives you something to start the conversation with.

10. Keep in touch with good people

If you meet someone you really connect with in a casual conversation, it makes sense to continue the conversation with them on another platform. You might make it a new long-term friend.

If you decide to do this, it is wise to avoid contacting a method that uses your real name or phone number. At least initially. For your security, invite to chat in Discord, Skype, or any other application where you do not need to use your real name.

If you’re sure you trust them after a while, you can add them to social media, WhatsApp, or another similar service.

Making occasional conversations the most interesting

With these tips, I hope you have a more complete experience when chatting online with random people. And even if you have to sort a lot of chaff on these platforms with a little patience and the right mindset, you can have rewarding chats online.

If you’re just talking to strangers for the passage of time, look at these hilarious random sites to help you procrastinate






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Photo credit: Sach.S /Flickr

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