A couple laying on hood of car playing a road trip game

15 Ridiculously Fun Road Trip Games for Two People

By: Melody

This post may include affiliate links. As an Amazon Associate, I (The Winding Road Tripper) earn from qualifying purchases. Read more

Are you looking for a new game to play with your road trip partner? If so, we’ve got you covered.

Whether you are a couple, family, or friends, we’ve devised a list of games to make your time in the car as fun as the destination. 

These games will provide hours of entertainment and laughter between two people traveling together. And we promise once you try them out, they’ll become part of your go-to list whenever you hit the road again! 

And we even found a way to add another “person” to your road trip game fun. ChatGPT! You can use AI to help you create and play games by allowing you to play with your travel partner. For example, you can play trivia together instead of one person asking the other the question. It’s great for more collaborative play.

So, without further ado, let’s dive into 15 road trip games for two!

21 Questions

Let’s start with the all-time classic of road trip games for two people. 

21 Questions is an iconic game that has lasted for a reason. It’s fun, the rules are easy to pick up, and you can tailor the game to match everyone’s personality. 

The game starts with one player thinking of a person, place, or thing in their mind. The other player then has 21 “yes or no” questions to guess what the first player thinks.

Every question needs to have a yes or no answer. 

If you’re trying to guess what someone else is thinking, it helps to start with broad questions that slowly narrow down to get it right. 

You win the round if you can guess the other person’s thoughts within 21 questions. If you’re feeling a little extra competitive, you can assign points based on how many remaining questions you have before getting the correct answer.

21 Questions using ChatGPT

If you and your travel companion want to play 21 Questions together, you can use ChatGPT to “think” of the object and then ask it questions. It’s fun, and I use the microphone function on my keyboard, so I don’t have to type the questions in.

Phone screen shot of playing 21 Questions using ChatGPT
Phone screen shot of playing 21 Questions using ChatGPT

Six Degrees of Separation

Here’s another road trip classic for two players.

Six Degrees of Separation got a second wind when it became an iconic meme in the early days of the internet known as Six Degrees of Kevin Bacon. 

The point of the game is straightforward. One player names two actors, and the other must connect them in six degrees of separation or less.

Here’s a classic example using Kevin Bacon.

“Kevin Bacon and William Shatner.”

William Shatner was in Festival in Cannes with Maximilian Schell, who starred in Telling Lies in America with Kevin Bacon.

This game does not have to be played with only actors. For example, you could do any person. For example, Eddie Vedder, the lead singer of Pearl Jam, and Bill Clinton, the 42nd President of the United States.

Six Degrees of Separation Using ChatGPT

Using ChatGPT for this game is fun. You can try your best to pick the most obscure pair of people and see if ChatGPT can connect them, or you can use ChatGPT to come up with the two people you need to connect. I like the later version.

If ChatGPT isn’t getting it right, try explaining the game’s rules and giving it more concrete instructions like I do in the screenshots.

Phone screen shot of playing Six Degrees of Separation with ChatGPT
Phone screen shot of playing Six Degrees of Separation with ChatGPT

Fictional Road Trip Families

One of the most fun things about a road trip is the people you will meet. 

However, some people you “meet” drive past you on the road at 60 miles an hour. While you don’t get enough time to meet them properly, that doesn’t mean you can’t tell a fun story about their lives.

The next time an interesting-looking car drives past you, you can collaborate on a fictional story about the family inside that vehicle. Take turns adding story elements and see where it will lead you.

The Movie Game

Here is another one for film buffs.

This game starts with one person naming a movie and the other person naming an actor who starred in that film. The person who picks the movie then names another actor from that movie and a different movie that the actor starred in. The second player then repeats the process, and the play continues until no one can name a new movie.

For a twist on this game, players can go back and forth naming actors, writers, directors, and production staff on movies until they cannot name anyone else involved with a given film.

Human Jukebox

Here’s a game for the musically inclined pair on a road trip.

Human Jukebox starts with one player singing a line from a song. Then, the other player uses the last line’s final word to connect the song.

Here’s an example:

Player 1 starts with a line from Queen’s Bohemian Rhapsody: “So you think you can stop me and spit in my eye. So you think you can love me and leave me to die. Oh, baby, can’t do this to me, baby.”

Player 2 connects it with Britney Spears’s classic “…Baby One More Time.” When I’m not with you, I lose my mind. Give me a sign. Hit me, baby, one more time.”

And the song goes on!

Two Truths and a Lie

Two Truths and a Lie is more than a fun game. It’s a great way to get to know your travel companion.

Here’s how the game works:

Name two truths about yourself and one lie. For example, you could say, “I used to have blue hair, I once designed a video game, and my aunt is a world record holder for women’s rodeo.” 

Your traveling companion will then have to guess which is the truth. The fun part is that you can make your truth and lies as straightforward or as challenging to guess as you’d like. 

This game is a fun way to explore your traveling companion’s history and discover unique and fun details about their life.

Name That Song: Radio Edition

Name That Song is a classic of road trip games for two. 

The usual way of playing this has one player singing a line from a song and the other player guessing the song’s name. 

However, you can play this game another way using local radio stations.

Turn on your radio and start scanning for random stations. Once you hear some music playing, the other player has to guess the name of the song and the artist before the song ends. You can take turns playing and score points based on who can get the correct answers.

This way of playing is fun because it allows you to discover the area’s radio stations.

Fortunately Unfortunately

Fortunately Unfortunately is a game that can get weird pretty quickly. Therefore, it’s a great game if someone in the car has their crabby pants on. 

It starts with one player saying something that starts with “fortunately: that’s positive, and then the next player saying something negative about that same event starting with “unfortunately.”

Here’s an example:

“Fortunately, we got time off work for this road trip.”

“Unfortunately, your boss got replaced by a zombie.”

“Fortunately, all those George Romero movies I watch have prepared me for this day.”

Continue this back and forth until you are ready to move on to the next game. 

The Road Trip Memory Game

Here’s a fun game to test your memory skills.

The game starts with the first player saying, “I’m going on a road trip, and I’m bringing…” 

They can name any person, place, or thing they want to bring on this road trip. Let’s say they said, “My guitar.”

The next player continues the game by saying, “I’m going on a road trip, and I’m bringing my guitar and…” and adding their own item.

The game continues until someone starts forgetting items on the list. Consider this game a safe way to forget what you must bring on your next road trip!

Radio Roulette

Radio Roulette can either be an exciting way to find new music you love or a challenging endurance test.

You only need to turn on the local radio stations and randomly pick one. You have to keep this station on for an unbroken 10 minutes to complete a round of the game. After 10 minutes, you switch to the next radio station and keep playing.

You might find yourself in love with some local Polka you would have never thought to listen to. Or you might be battling through 10 minutes of local talk radio.

Who Wants To Be A Millionaire?

In the mood to win $1,000,000? There might not be a stack of hundreds on the table, but you can have fun playing along.

The Who Wants To Be A Millionaire app is a great way to play a game with just two players on your next ride. One player hosts this iconic game show while the other gets to be in the hot seat with a shot at a cool million dollars.

And if you like these app-based road trip games, plenty of others are in your app store.

Who Wants To Be a Millionaire Using ChatGPT

Who Wants to Be a Millionaire is a trivia game, so it’s easily played with ChatGPT.

Phone screen shot of playing Who Wants to Be a Millionaire with ChatGPT
Phone screen shot of playing Who Wants to Be a Millionaire with ChatGPT

Did You Hear That?

No, this game isn’t about that strange noise from the engine. It’s a fun game that tests how up-to-date you and your travel companion are on current events.

This game can be about emerging events in the news, the latest updates from your favorite bands, or any other current events topic that the two of you are into.

To start this game, ask your travel companion, “Did you hear that X?” and replace the “X” with whatever current event you want to quiz them on. 

Here’s the twist: the current event you just discussed doesn’t have to be accurate.

You’re trying to trick your travel companion into thinking that whatever you’re talking about really happened.

If you trick them, you win the round.

Cuisine Quest

Traveling throughout the country, you’ll see sights that might seem strange. 

Local cuisine is one of the most exciting things that change as you move to the country.

Next time you two stop at a gas station, you must purchase an item you’ve never had. The goal is to be the one who discovers the most unique local snacks on your road trip!

Bad Film Plots

Usually, when you play a game, you want to do everything right. However, Bad Film Plots has you intentionally doing everything wrong.

The goal of this game is to explain the plot of a movie as badly but as accurately as you possibly can. The other player must guess the film you’re talking about correctly.

Let’s say you wanted to explain the plot of Terminator II: Judgement Day badly. You could say: “A down-on-her-luck working single mother makes an unlikely friendship as her son discovers a father figure.” 

That might be a little tricky, but that’s the whole point of the game. 

Local Trivia Night

One of the most significant advantages you have when taking road trips today is that you’ve got the whole internet by your side while on the road.

Use that to your advantage and do a local trivia game while traveling. 

One player gets to be the trivia master, asking questions about the state you’re driving through, and the other person is in the hot seat, attempting to come up with clever answers.

Trivia with ChatGPT

Trivia is probably the easiest road trip game for ChatGPT to help out with. Tell it what subject you want trivia questions for, and it will spit out some questions you and your travel companion can answer.

Phone screenshot of playing trivia with ChatGPT
Phone screenshot of playing trivia with ChatGPT

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