100 Modern High-Level Random City Encounters

Below you’ll find 100 modern random city encounters for high-level characters in your tabletop campaign. For even more random table goodness, check out Random Encounters AI today!

1) Players see a man in ripped jeans and a Metallica t-shirt that’s seen better days. He stops and stares at the sky, mumbling about the end of the world. He doesn’t react to players’ inquiries.

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2) A group of students come around the corner, heading for the library. They’re wearing backpacks and talking about their online classes.

3) As players walk down an alley, they hear a scream. They round the corner to see two women beating up a man. He’s holding his face and crying.

4) Three teenagers are kneeling in front of a busted streetlight, setting up a camera tripod. They’re taking pictures of the broken light.

5) A man comes out of an apartment, yells at players for loitering, then goes back inside.

6) A man in an apartment window is yelling into his cell phone about his girlfriend. He’s swearing at the top of his lungs.

7) A car drives by, blaring music.

8) A man is lying down on the sidewalk, sleeping.

9) As players walk down the street, they hear a dog barking in an apartment building.

10) A woman is yelling at her child in an apartment.

11) Two men in suits see players and make a phone call. After a minute, they walk up to players and ask, “You guys seen any suspicious characters around here today?”

12) As players walk down an alley, they hear a scream. They round the corner to see a customer kicking a store clerk. The customer is Fat Fingers Hones, a local mobster that’s well known for his temper.

13) Paulie Nuts, a local gangster, bumps into the players and demands an apology. If they do not apologize quickly or sincerely enough, the entire Nuts family will be after the players until the elders think the debt is paid.

14) Two highly skilled bounty hunters have the players in their sights. They’re having a friendly competition to see who can take the players down first.

15) As the players walk down an alley, they hear muffled sobbing. They round the corner to see a woman and her child, huddled in a doorway. She thinks their apartment building is haunted and wants to move, but can’t find a new place to live. The party can fight the ghost, help her find a new place to live, or just walk away to the sounds of her sobs growing louder.

16) A SWAT team descends on the players, mistaking them for a crime organization. The team has the players at gunpoint, but are willing to listen to reason.

17) A car drives by, playing loud music. It stops nearby, the doors open, and four or five teens get out of the car. They’re hopped up on drugs and attack. Killing them will have negative consequences for the players.

18) A street performer is juggling fire. If players come closer to watch, 2d8 of his buddies will surround them and demand all valuables.

19) A drunken man stumbles into the players, asks for directions, then walks off in the wrong direction. He’s a hacker who just hooked into the characters’ cell phones.

20) Two hackers have the party in their sights. As a result, the players will find mysterious charges on their cell phone bill.

21) As players walk by, they hear a baby crying in an apartment.

22) A street performer is singing the national anthem.

23) An escaped pride of lions attacks!

24) A man with armor and a machine gun attacks. He’s suicidal and on some sort of drug. He’ll try to take as many people with him as possible.

25) A large group of protesters have gathered at a nearby square. A riot is happening. There’s a chance the players will be arrested, even if they’re not involved. They’re gonna need lawyers.

26) As the players walk past a store, a group of teens wander by and bump players. They demand an apology and start a fight if they don’t get one. If players fight back, the teens will record it on a cellphone and upload it immediately. The video will go viral and paints the players in a bad light.

27) Two men are on the roof of a building, looking for an antenna. They are mercenaries working for a rival organization. They are watching the players’ every move.

28) A group of teens are loitering in front of an apartment building.

29) A news crew is interviewing a witness of a recent crime. A drive-by happens during the interview. The witness is taken out.

30) A man on the street is complaining that his vehicle has been towed. He claims he just parked there to get a bite to eat. He’s lying. If players say anything, he will become irate.

31) Three elderly ladies are sitting at a bus stop. They’re swapping stories about their grandchildren.

32) The sound of sirens is nearby. The players can see red and blue lights. It’s a runaway ambulance.

33) A man is yelling at his phone. He’s been playing Pokemon Go, and he got “stuck” in a building. He’s mad, and a lot of people are watching.

34) A woman in a business suit bumps into a player, then apologizes.

35) Fourteen deranged monkeys escape from the zoo and attack the players at an inopportune time.

36) Up ahead, the players see two men in suits. One is blond, the other is bald. They are part of an international crime syndicate, and they are observing the players.

37) A man is standing on the corner blaring music from his phone. He’s actually a sniper spotter. If players aren’t careful, they’re gonna get shot.

38) The players overhear a conversation. Two men are talking about an illegal street race they’re planning to attend. If the players go, they’ll be asked to pay a fee. If they refuse, they’ll be attacked.

39) Four teenagers are goofing around, climbing on the statues in the city park.

40) A dog starts barking. It’s a trained attack dog, but it’s actually friendly unless the players say the word, “Dude.”

41) A man is trying to sell the players a new computer virus. He’s an undercover FBI agent.

42) The players come upon a homeless man. He is actually a retired illusionist working as a street magician. He waves at the players and points to a nearby building. An apartment window opens and a bouquet of flowers drops out. The illusionist’s wife is in the apartment.

43) The players walk past an apartment building. A woman opens the door and hands the players a cell phone. The screen is cracked, and the phone is ringing. It’s an anonymous tip. If the players answer, they hear a gun shot. The cope will come to talk to them about this incident and why they had the phone. If they got rid of the phone, it will be worse for them. They’re gonna need lawyers.

44) The players witness a mugging on the street. A group of teenagers surround an older woman on the street. They’re threatening her with knives.

45) A police officer walks up to the players and asks for their names. He says there’s been a report of “suspicious people” in the area, and he’s checking IDs. He’s lying.

46) A man in a suit is shouting at a cab driver. The man is clearly drunk and is holding a wine bottle. If players intervene, the man will thank them and offer them a free drink. He’s not a bad guy. He’s just had a bad day.

47) A street performer is juggling bowling pins and chainsaws. If players come closer, 1d6+4 of his buddies will surround them and demand all valuables.

48) A group of teens are loitering in front of an apartment building. They’re up to no good.

49) Gunshots ring out a block away. If players go to check it out, they will see a car on fire. The driver has been shot.

50) A man is handing out fliers on the street. He is actually spreading a disease.

51) Several old men are arguing about baseball and basketball and whether or not they can play in their old age. They’re drunk.

52) As players walk down the street, they notice a group of men from a rival organization. They are carrying weapons. It’s a setup.

53) Two men are fighting. One is a street performer. The other man is a rival street performer.

54) A man is asking strangers for a cigarette. He’s actually a vigilante, and his family has been killed by a drug cartel. He wants revenge. He thinks the players are involved.

55) Two people are handing out fliers. They are collecting signatures for a petition. They want to tear down City Hall and plant a public garden for marijuana.

56) Three Burmese refugees are asking people for food. They have been in the country for a month, and they have been starving.

57) A group of 2d8+4 military commandos attack the players when they least expect it. They are trying to bring down a rival organization.

58) A young couple is making out against a building. The players will attract attention if they go past them.

59) A woman is asking strangers for a cigarette. She is actually a medium. She is trying to contact the spirit of a girl who was killed by a drunk driver.

60) Three men are arguing about sports. One of them is a little too passionate in his argument. He’s a bit violent.

61) A group of 4d4 teenagers are loitering in front of a building. They are trying to incite a riot.

62) A man is offering to sell a pizza for a dollar. He is actually a con man. He has a deck of cards in his pocket, and he’s cheating people.

63) An old man is panhandling. He’s deaf. If players give him money, he will respond, “Thanks, man! I will buy a beer!” Then he won’t buy a beer. He doesn’t remember he just got money.

64) A woman is trying to sell flowers, but she’s having an identity crisis. She thinks she’s a tree.

65) Two actors are rehearsing a skit for a play. They are arguing over the dialogue.

66) A man is wearing an eye patch. He is pretty grumpy. If players make fun of his eye patch, he will attack.

67) The players see a man in a suit arguing with a cab driver. The man is trying to get a ride, but the driver doesn’t have any more room.

68) A group of 2d6+2 armed thugs attack the players and ask for their money. They are actually looking for a rival gang.

69) A woman is offering free hugs. She’s actually a mind-control agent. She wants to control the players’ minds.

70) A man is asking strangers for a nuclear launch code. He appears deranged, but he’s actually a scientist with a top secret project.

71) Two rival unions are fighting. The players can sympathize with one of them.

72) A group of 2d8 cops are searching for a lost child. He is a little boy, and he is hiding from them.

73) A woman is lying on the sidewalk. She is an actress, and she is rehearsing a skit for a play. If players disturb her, three bodyguards will attack.

74) A group of 2d8 businessmen are holding a secret meeting. If the players eavesdrop, the meeting will end immediately.

75) A man with a black eye is selling a second-hand car.

76) A group of 2d4 teenagers are holding a party. They have a keg of beer and a boom box. They will attack if players interfere.

77) A man is selling tickets to a concert. He is trying to pass them off as VIP tickets. They are regular tickets.

78) As players turn the corner, they see a group of 5d4 street musicians. They are playing old-time music. They are actually a group of stage magicians practicing for a show. If players stop to watch, pickpockets will attack.

79) A woman is trying to sell counterfeit DVDs. She will attack if she’s caught.

80) Two different street performers are arguing over who has the best act. If the players support one of them, he will attack the other one.

81) A group of 2d6+4 thugs are looking for a rival gang leader. They are carrying weapons.

82) A man is giving out free samples of soda. He is actually poisoning people.

83) Two people are arguing over a parking space. They are pretty angry. If players get in the middle of it, a fight will break out.

84) An escaped prisoner runs up to the players and demands a ride. He has a gun and wants to escape the city. He will attack if he is caught.

85) A group of 2d8 teenage boys are horsing around. They are doing stupid things, and they are bothering strangers.

86) A man is making balloon animals. He makes an elephant. If players try to buy it, he will say, “Sorry. I don’t sell to animals.”

87) A man is fighting with a pigeon. He wants to eat it for dinner.

88) As players pass the local library, they notice a group of people trying to break into the building. They are actually a group of 3d6 juvenile delinquents.

89) A woman is trying to sell magazine subscriptions. She is actually a shaman. She is trying to spread a curse.

90) When players get to their destination in the city, a man will rush up and tell them, “You can’t park here! The parking meter is broken.”

91) A man is selling joints. The joints will actually cause an allergic reaction.

92) A man is selling sandwiches for a dollar. They are actually horse meat. If players eat them, they will get sick for 2d12 hours.

93) Overhead, players see a runaway blimp. It looks like it’s going to crash.

94) Thirteen mobsters are taking a shortcut through a park. They attack players on sight.

95) As players walk down the street, they see a man in a police uniform. He’s actually a con man. If players approach him, he will claim to be a police officer and arrest players. He will try to collect a bribe.

96) A group of 2d4 businessmen are arguing. They are trying to hire a group of ninjas to kill a rival businessman. They offer to hire the players.

97) A man is arguing with a police officer. He thinks he can get out of a ticket. He can’t.

98) Players see a crowd of people standing around a man. He has lost his arm and he is bleeding. The players can help him.

99) A man is standing on a roof. He is trying to jump. If players try to talk him down, he will jump.

100) A woman in a red dress tells the players, “Cecil just asked me to marry him.” She’s lying. She’s a con artist.

AI + Procedural Generation = Worldbuilding Tool of your Dreams...

Coming soon to LitRPG Adventures Workshop...

Or check out my ChatGPT Backstory Generator

Paul Bellow

Paul Bellow

Paul Bellow is a LitRPG author, RPG game developer, and old school webmaster. He's been playing tabletop games since the 1980s. He started Random Tables RPG as a way to give out free D&D and Pathfinder content to the world. Enjoy!