Social Media

10 Tips to Start Random Chats Worth Having

Ben Stegner Updated 20-05-2020

Sites like Omegle and Chatroulette are well-known for connecting you with strangers when you want to have a conversation with someone. Anyone. A lot of the time these conversations are weird, but what if you want to take your random chats to the next level?


In this article, we list some tips to start better random chats worth having, whether on Omegle or other similar sites. Meanwhile, you may also want to brush up on conversational mistakes you may be making.

1. Use the Right Service

Emerald Chat

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

If one-on-one chats bore you, try another service like, which offers random group chats. Meanwhile, Y99 offers multiple chat rooms grouped around different topics.

Our advice on starting random chats online should apply no matter what services you use.


2. Decide on Text or Video Chat

Before you start chatting, you’ll also need to decide whether you want to use text-only chat, or turn on your webcam and microphone for video and audio chat. Both have benefits and drawbacks.

Text chat is better if you’re uncomfortable with showing yourself to strangers. You can also take a minute to come up with responses instead of having to speak in real-time. However, it’s also easy to be lazy in text chat. You’ll get plenty of “ASL?” messages to start conversations, with nothing of interest said afterwards.

Video chat, meanwhile, lets you put a face to the person you’re talking to. If you’re both involved, it’s a much more rewarding experience. Of course, the major drawback to video chat is that many people use their webcam for inappropriate purposes. If you’re not comfortable with people doing this, stick to text chat.

3. Ask Interesting Questions

Life Goal Chat


It’s too easy to fall into the same routine of asking how someone’s day has been, what they do for a living, and similar boring questions. To get more out of your random chats, try asking deeper questions that will elicit more interesting responses.

This might feel a little awkward at first, but if people are intrigued, you’ll have far more personal discussions. Some example questions include:

  • If you could invite anyone in the world to dinner, who would it be?
  • What is your life goal right now?
  • What’s the hardest event you’ve ever lived through?
  • If you could change one event in history, what would it be?
  • What’s your biggest regret?
  • What is your favorite smell and why?
  • How is your relationship with your family?
  • When did you last embarrass yourself?

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

4. Try Talking to People From Other Regions

If you use sites that are popular in your country, you’re likely to only talk with people from your own area. The same goes for the time you chat—if you’re online at a normal time for your region, you’ll probably run into people who live nearby.


To mix this up, try seeking out other chat sites, such as Chatroulette 6 Chatroulette Alternatives to Chat With Strangers Online for Free Chatting with strangers online can be a fun way to get to know new people. Here are the best Chatroulette alternatives. Read More that cater to different areas of the world. You can also try visiting chat sites in the small hours of the morning, or at other odd times when people from across the world are more likely to be online.

By talking with people from other countries, you’ll have more chances to ask about life in different parts of the world. Give this a try if your usual routine doesn’t yield any interesting folks.

5. Include a Friend

Most random chat services don’t let you invite people to text or video-based chats. Despite this, having your friends physically join you for chats can make the experience more enjoyable. Of course, this makes the most sense for video chats.

By having two (or more) people on camera, you won’t feel the pressure of a one-on-one conversation. You can bounce topics off of your buddy when you’re not sure what to say. When the other person sees that you’re not alone, the chat should become more lighthearted.


And when you come across weirdos, you can laugh about them with your friend instead of getting creeped out by them. It’s a fun activity when you’re together and not sure what else to do.

6. Keep a Record of People You’ve Talked To

Putting a pin in the globe

If you chat online often, why not make a little project out of your experiences? After you’ve talked to someone for a bit, ask them where they live (generally). After a while, you might buy a map to log where the people you’ve met online are from.

One particularly fun option is to buy a scratch-off map, either of your country/continent or the whole world. Otherwise, you can use pins to mark the locations on a regular map. And if you don’t like the map idea, maybe you could start a blog detailing the various hometowns you’ve discovered?

Scratch Off World Map Poster Scratch Off World Map Poster Buy Now On Amazon $15.08

This will help your online chats to feel like a journey over time.

7. Play a Role

Mask Disguise

Are you bored of acting like yourself all of the time? Then why not try pretending to be someone else once in a while?

Instead of responding as you would, try acting like a character from a movie or a famous figure. See if the other person can pick up on who you’re impersonating.

Of course, this strategy might not help you get to know people, and you should never do anything to make people feel uncomfortable. However, if you struggle to talk as yourself, it could be a good way to become more comfortable with the process.

8. Filter the Junk

Real Conversation Omegle

The chances are that you’ll come across all kinds of spam accounts and people asking about inappropriate subjects when striking up random conversations online. Don’t waste your time with these. If someone starts being creepy, sends you automated links, or seems like a bot, just disconnect and move onto the next person.

You might also consider making it clear what you’re looking for from the start. When someone connects, you can paste a message like “I’m looking to have a real conversation, so if that’s not what you’re here for, please disconnect now.” While this sounds a bit harsh, it will make your time more efficient by weeding out people you wouldn’t want to talk to anyway.

9. Bring in Media

Struggling to come up with a conversation topic? Try using media from elsewhere to generate some ideas to talk about. You could share a YouTube video, a playlist of music, a funny meme, or anything else you’ve recently come across online.

Similarly, if the site lets you define your interests, add a few so people know what you like to talk about. Most people enjoy finding new content and discussing common interests, so that will give you something to strike up a conversation.

10. Stay in Touch With Good People

If you meet someone you really connect with on a random chat, it makes sense to keep talking with them on another platform. You might make a new long-term friend out of it.

Should you decide to do this, it’s wise to avoid connecting with a method that uses your real name or phone number. At least initially. For your safety, invite them to chat on Discord, Skype, or another app where you don’t have to use your real name.

If you’re sure you trust them after more time, you can add them on social media, WhatsApp, or another similar service.

Making Random Chats More Interesting

With these tips, you’ll hopefully have a more fulfilling experience when chatting online with random people. And while you will have to sort through a lot of chaff on these platforms, with a little patience and the right mindset, you can have some rewarding chats online.

If you’re only chatting with strangers to pass the time, check out these hilariously random websites to help you procrastinate 15 Hilariously Random Websites to Help You Procrastinate The Internet is full of weird stuff. Kill some time with these websites that'll make you wonder why they were ever created. Read More .

Image Credit: Sach.S/Flickr

Related topics: Chat Client, Online Chat, Online Community, Video Chat.

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    April 20, 2015 at 5:00 am



  2. Cerona
    March 17, 2015 at 4:01 pm

    It's very dangerous to chat with strangers so I installed PCWebControl software on my sons computers...

    • EEVV
      July 5, 2016 at 11:25 am

      Makes as much sense, as a toaster having a touch screen. Good job, lady. Keep the streets clean.

  3. Zhong
    February 28, 2015 at 4:55 am

    Isn't it dangerous to chat with strangers? Obviously, kids was taught the phrase, "never talk to strangers". This message seems to be wrong as they grow older but in what way should we permit ourselves on talking to strangers.