18 Date Friendly DOS Games


If I could sum up my overarching personality, in a manner applicable throughout my entire life, in one, single phrase, it would probably be: “fondness for DOS Games”. In contrast, Dion was a complete Nintendo junkie as a young boy, so missed out on a lot that DOS had to offer.

A lot of classic DOS games are either Shareware, Freeware, Abandonware or even recently remastered. This means they’re very easy to locate online for direct play or download. Often for free. The great thing about early DOS games is that their technical limitations often led to an excess of variety and creativity. And as home internet wasn’t common at the time, there’s a slew of co-op options to choose from.

Rather than force him to watch me speed run the Commander Keen series (again), below are a few gems I’ve introduced Dion to over the years. Most of these are blatantly fit for co-op play, but a few facilitate what I’m calling ‘backseat gamer’ or ‘keyboard passing’ modes. These are still super fun to play together, despite not explicitly being multiplayer games. I’ve also held back from including the well-known and commonly known FPS titles, like DOOM/Duke 3D, in an effort to reference more unique experiences. Enough preamble, let’s play!

Wacky Wheels

Wacky Wheels DOS Co-op

Wacky Wheels and Skunny Kart were the PC competitors of a similar well-known series featuring that one Nintendo mascot. Wacky Wheels was my preference, by far. Alongside your standard split screen multiplayer, Wacky Wheels also featured a battle mode where you pelt hedgehogs at each other. That’s what I call well-rounded fun.


Jetpack DOS Co-op

Jetpack technically has a 2-player mode, but it’s really just a glorified turn taking device. There’s nothing wrong with that, especially as the levels are rather short. It’s a fun little platform game, with some unique gameplay factors to keep things fresh. It also boasts a nifty level editor if you want to add a more personal element to challenging each other.

Scorched Earth

Scorched Earth DOS Co-op

Strategy, explosions, funky bombs.

In randomly generated fields, you, your partner, and optional computer players can fight to the death. The array of items in this game really helps to keep gameplay from getting stale. It’s kind of like a granddaddy to Worms, in general gameplay style.

Scorched Earth was Dion’s pick of the bunch out of all the Emmy-enforced, co-op, DOS game experiences. When I asked him why, he said it helped him to use math in a fun way, which I’d honestly never considered. And it sounds kind of lame, so let’s forget he said it. But first, if you/your partner are part of Gen Y, Math Circus is worth a stealthy mention, too. For a huge nostalgia hit, sit down with your date and give it and its (sometimes surprisingly challenging) levels a spin…

OMF: 2097


One Must Fall: 2097 is peak DOS fighting game. Each player pilots a giant, 3D robot, all with distinctive special attacks. The variety of battle arenas aren’t just for aesthetics – all but one contain unique hazards, too. Fun to play, fun to master, and easily a top pick.


Boppin Dos Co-op

Boppin might be my number one pick if it wasn’t so finicky to calibrate on modern computers. It’s a block-matching puzzle game which allows for 2 simultaneous players. You puppeteer one of two martini-shaped avatars – Yeet and Boik. With a simplistic yet satisfying story concept, and new tilesets for every level, Boppin masters world building like no other puzzle game before it. It keeps things exciting by promoting constant flushes of anticipation (and a smattering of violence to spice things up).

As mentioned earlier, it’s quite tricky to get working in 2-player mode on a modern PC. However, if you have a dusty 486 lying around in the garage, it’s worth booting it up for Boppin.

Fuzzy's World of Miniature Space Golf

It’s mini golf, Emmy. There are stacks of mini golf games. What’s so special about this one? Well, like many other DOS games, it hones in on what it wants to do, and it does it well. The graphics, soundtrack and gameplay are all distinctive. Its addictive, isometric space aesthetic will make it worth your while.

Trivial Pursuit

There are several versions of TP for DOS, but I’m personally endorsing the 1992 edition as most worth your while. It’s essentially an interactive PC version of the classic boardgame, narrated by a slightly irksome… peacock? Honestly, identifying exactly what he’s supposed to be is probably more difficult than a significant range of the questions he asks you.

It’s fairly immersive, with bright VGA colours paired alongside frequent audio and visual cues. If you’re a fan of the boardgame, definitely give it a whirl.


Cyberdogs DOS Co-op

Cyberdogs is a top-down shooter featuring randomised maze-type levels. It’s fairly straightforward, but good fun nonetheless. If you or your partner find First-Person Shooters intimidating or unenjoyable, this is a good starting compromise. Or maybe even a weaning tool if you’re particularly determined!

Adventure Games


There are so many of these that are worth your while that I really don’t think it’s fair to pick one specifically. While not co-op games, they’re mighty enjoyable to deconstruct as a duo. If one of you has played the game before, they can control the keyboard/mouse, while the other gives directions. LucasArts classics such as Day of the Tentacle, LOOM, and Monkey Island are a great starting point. The surprisingly and delightfully well-known Hugo’s House of Horrors series features games which are more brief, but charmingly memorable. Sierra’s additions are much less forgiving, but extremely engaging. Entries such as Conquests of Camelot, and the Kings Quest series are some standouts, amongst many more.

Flying Tigers II

Flying Tigers II

To be fair, this is probably the game I’m least passionate about on this list. It’s a top-down scrolling shooter. There are dozens of these, and they’re all quite similar. But I did spend a fair bit of time playing it as a child, and it hits all the markers for a decent game. If you’re a fan of the genre, it’s worth a whirl.

Win Lose or Draw

WLD Dos Co-op

It’s time for the game-show segment! I love this one more than is reasonable. For some reason, I’m a bit of a maniac for any games that involve drawing. It’s a bit like Pictionary, but the PC does the drawing and you do the guessing. Definitely a bit of fun if your eyes can handle the CGA palette and polygon-headed player sprites.

Classic Concentration

Classic Concentration

Speaking of harsh palettes, this game most certainly has one. Harsh soundtracks? In SPADES, my friend. But sometimes the hankering for pictorial puzzles masked with memory games overrides all taste. I guess. Some silly fun to be had here, which always gets surprisingly competitive.


Lexi-Cross DOS Co-op

Lexi-Cross is another word-based, game-show style game. The graphics are fantastic, especially for the time-period, and the sci-fi vibe makes it all that more memorable. Of all the games listed, this one unfortunately seems to be relatively unknown. I’m 100% here to encourage the reinvigorated, Lexi-Cross renaissance.


SkyRoads DOS Games

SkyRoads has you piloting a spaceship over various cosmic-themed pathways. Featuring some of the best MIDI cyberpunk tunes 90’s gaming had to offer, it’s worth it just for the soundtrack. Depending on the level, you’re impacted by factors such as gravity, fuel, grip and… combustion. Each level takes only a minute or few to play whether you win or lose stopping boredom from setting in while you wait your turn.

Where in the World is Carmen Sandiego?

Carmen Sandiego DOS

Everyone knows Carmen Sandiego, right? As Dion mentioned in an earlier article, I exclusively credit my middling knowledge of geography to the Deluxe, 1990 version of this series. Just in case you’re not familiar; you play an unseen detective, travelling around the world, following clues to bust ludicrous criminals. It’s fairly simplistic and straightforward, but is one of the more memorable and genuinely enjoyable educational games playable as a duo.

Ski or Die/Skate or Die

Ski or Die!

I described these two to Dion as, “Sort of like California Games, with a bit more edge.” They were definitely the epitome of cool for a little girl playing DOS games in the 90’s, anyway. You and your partner can take turns competing in a range of SIIIICK events. They’re pretty fun, with a bunch of little gameplay Easter Eggs scattered throughout.

The Incredible Machine


Another game with multiple iterations, the 1993 version is TIM in its prime. A puzzle game, where you construct simple-to-elaborate Rube Goldberg machines, to solve various objectives. Great fun to play as a pair, as creative and logical brains both lend prominent strengths to gameplay. Free play mode can also be an absolute riot.

Arcade/Console Ports

Simpsons DOS Games

If despite the above, neither of you are feeling the unique DOS vibes, there’s always ports of other games to consider. Arcade/Console ports of multiplayers such as The Simpsons Arcade Game, Street Fighter 2 Turbo, Bomberman and Bubble Bobble are all keen to satiate your retro gaming tastes. Do keep in mind, not all ports hold up to the originals, and the woeful ones run the risk of desecrating something you love.

Okay, I lied. I crammed way more than 18 games into this article. Did they ring any nostalgia bells? Dilate your DOS diodes? Or did I miss your favourite? If so, please let me know in the comments, so I can make it mine.

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