Old School Chat Games you can Play Online

Even though our smartphones and computers may be full of cutting-edge games and chat apps, sometimes it makes a refreshing change to go old school. Sure we can chat all day on WhatsApp or Kik, play Fortnite or PUBG while talking trash but sometimes, stepping back and going old school hits the right spot. Here are some old school chat games you can play online with your friends or family.

These are all versions of old family games you probably used to play on road trips or long journeys to pass the time. Even though they could be decades old, they can still while away a relaxing couple of hours with friends or still help a journey pass faster. You can play them as is, or adapt them to your needs, it is entirely up to you.

Before you roll your eyes and move on, consider that each of these games can be tweaked to suit your age, who you’re talking with and what mood you’re in. They are more than games, they are exercises in imagination, tools to get to know someone, icebreakers to help make new friends or just something silly to pass the time. The mechanics may be decades old but the execution is entirely up to you.

Old school chat games you can play online

You can play these chat games online or over SMS, whatever works best for you. Either way, they can make a boring time a lot more sociable!

I Spy

Let us begin with the all-time classic. I Spy is made more difficult by not being in the same place as the person you’re playing with but that just adds to the challenge. Start by telling the other person where you are and then play the game as normal. That at least gives them a chance to picture your location.

You can adapt this to include people, cars, buildings or whatever you like. With the right imagination, I Spy is far from the lame game you used to play with your siblings!

Story Time

Story Time can be dangerous or a bit of harmless fun depending on the mood and who you’re playing with. That’s what makes it still such a good game to play even when you’re no longer a kid. One of you begins a story in a single sentence. The other continues with a single sentence and you swap from there.

As long as you both have good imaginations, this game can take you places you would never have believed. Even though I’m a long way from childhood, I still play this game with some of my other writer buddies.

Would You Rather?

Another old game but gold. This is shorter and faster but is a decent game for waiting rooms, between classes, lunchtimes or whatever. Half the challenge is coming up with interesting or challenging options for the other person to choose from. It works well over SMS, chat or email so is ideal here.

In case you haven’t played it, the idea is to offer two choices of something and the other person has to say which they would rather do. For example, dance naked in the street outside or kiss the old lady/man next door. Again, it’s a childhood game that can be adapted to your current age.

Twenty Questions

When I was asking around about simple chat games to play, almost everyone suggested twenty questions. Some restricted it to NFL or NHL players, some restricted it to faculty members or famous actors but you can play it exactly how you like, about anyone or anything you like.

This game is as old as the hills and is used a surprising amount in getting to know a new partner. Three people I asked all said they suggest this game over text when getting to know someone new.


Our world is filled with silly abbreviations and acronyms and this game plays on that. You can go one of two ways. You can use real life options and see if the other can guess or you can make up abbreviations and see if the other person can guess them. I personally know of two girls who often play this game when describing boys. You can imagine how that one goes!

Personally, I prefer the making up abbreviations version. It isn’t as dry and can be a lot of fun with the right play partner.

What If?

What If? is another game I play regularly and it can develop some very interesting ideas and situations. The discussions afterwards are often more interesting than the game itself.

For example, you could text or post ‘what if all the lights went out in the city right now’. You then message back and forth what you would do. The trick here is to ask open questions and to leave them as open as possible to maximize the potential for randomness. As a writer of short stories, I like playing this game with like-minded others to generate ideas. You would be amazed at how different or random some of the answers will be!

Truth or Lie?

Truth or Dare is a little difficult to play online so it might be easier to play Truth or Lie. You each have to come up with three things, two true and one a lie. The other person has to guess which is which. This can be about anything from things you have done, places you have traveled or people you have seen or met.

Like all of these games, it can be tuned to your age and who you’re playing with and can be clean and sensible to completely the opposite.

Did it Happen?

Our final chat game is a variation of Truth or Lie. You make a statement about something and ask the other person if it happened or not. It is similar enough to Truth or Lie but different enough to engage you differently.

For example, you could say ‘Did you hear that there’s a new phone released that will bend in half?’ The other person has to say ‘That didn’t happen’ or ‘That happened’. There is an element of trust involved if you’re going to be talking about current events but is otherwise a good chat game to play.

Got any other chat games you can play online or over text? Tell us about them below if you do!

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