What’s a sketchy situation you willingly put yourself in that could have ended badly but didn’t?
September 2, 2025
What’s a sketchy situation you willingly put yourself in that could have ended badly but didn’t?
25 comments
When I was young and dumb I got the brilliant idea to walk from the pub to my flat alone at 1 A.M one night during Uni instead of taking a cab. I got followed by a strange man, if it hadn’t been for a very convenient policeman I was about to have to make a run for it and hope for the best.
In my early 20s, I invited guys I knew from an online forum to crash at my place while they were in town. I am 40, I still do this, made a lot of lifelong friends that way.
Hookups are always at least a little bit scary but one time when I was 20ish I woke up to the guy using my hand to pleasure himself. I was veeeery careful navigating that situation and I made it out with only one additional violation
number one is that when i was young and dumb and thought i was invincible and also drunk and on ecstasy i climbed to the top of an old water tower on the roof of an industrial building in the bronx. that still gives me shivers thinking about how lucky i was
One night stand with a guy I barely knew. Could’ve gone either way.
I was stuck in a foreign country and had to get back to the airport. A guy said he’d give me a ride in his white van with blacked out windows.
Ended up taking it. There were a total of 5 strange men in the van and me.
He kindly dropped me off at the airport.
I was driving for Uber. Had a passenger that was coming from the bar. He needed to make a couple stops and I said that was fine, they were on the way. He stopped at Walgreens for kitten food because he had just rescued some. We got talking about kittens and he asked to stop at his flower shop he owned. Yup, no problem.
He goes inside for a bit and comes out with a big bouquet. He told me he was taking them home for a friend. We get to his house. He goes to leave and then gives me the flowers and says they were actually for me. Then he asked if I wanted to go inside and see the kittens. I said sure, absolutely. I go in and hang out for almost an hour playing with the kittens and chatting some more. Suddenly, he kisses me and asks if I’ll be his girlfriend. I’m 27 at the time. This man is 55-60. I awkwardly laugh and tell him I’ll think about it and told him I had to go. He asked for my number to get ahold of me later, and I told him I had it from the Uber app. He accepted that and I left.
The next night I got a message from Uber claiming a passenger had left something in my car and needed to get ahold of me. I told Uber that that was not true and I would not be reaching out to the passenger.
I went with my ex-roommates to DragonCon one year, if you don’t know what that is it’s a huge pop culture convention in downtown Atlanta. We got into an argument and I decided to walk away from the area of the con and try to figure out a way home late at night. I’m a 4’11” and 90lb female. My ex roommates tracked me down and were like “That was so dangerous, a homeless person could’ve grabbed you and r*ped you”
When I was 12 I ran away from home with no phone and no shoes in the middle of winter. I’d wised up and started to head back when a stranger offered me a ride.
He turned out to be a nice guy and did just as he offered. I’m actually really grateful for that but it could have gone very wrong quickly.
I was in a foreign country, met a man at a bar, got in his car where he drove me to a small apartment complex to pick up some marijuana. We ended meeting up with his cousin, they had a whole conversation in a language I don’t speak. Then he drove the two of us (me and him) to a remote beach and tried to hook up. I so sketched out I asked to go back to my hotel. LUCKILY, he wasn’t a bad guy and drove me back right away. I was 20, Dumbest thing I’ve ever done
When I was 16 my guardians allowed me to drive over two hours away to meet a boyfriend I met through the internet in person. He was in fact a POS, but when I reflect on that time I think about how I could have been murdered, assaulted, etc and none of the adults in my life even cared.
Hitchhiking by myself to a club at night. I live in South Africa, this was not a good idea but I was 19 and invincible. A car full of guys stopped to pick me up and I just got in with zero fear. They were very friendly, they gave me some of the rum and coke they were drinking, and they dropped me off at the club with zero issues. One of my favourite and most irresponsible memories, lol. The 90s were wild.
Oh jesus.
Half of the situations from age 12-21 were reckless as hell.
How about this one:
I was an 18 year old census taker and had to collect the census at a trailer park in 2010.
I knock on the door and a shirtless old man with pig tail braids answers the door angrily with a cigarette in his mouth. I explain who I am and he is visibly irritated that ‘the government’ is at his door and nearly runs me off his property, but then changes his mind and invites me to come in and sit down in his living room. I come right in and sit down.
I complete his census info, which leads to a conversation about his heritage, and we actually become friends and I come visit him and sit in his back yard while he rolls cigarettes and tells me stories about the sixties and the American Indian Movement the whole summer.
He moved out of state the same summer, but I stayed in contact. He’s kind of out there and still sends me spaced out ‘one love/vaguely conspiracy theory-esque’ youtube videos through facebook messenger to this day. That was 16 years ago and I am still a fairly trusting person but I think about what that actual scene was originally, and that was pretty stupid of me to just walk in to his house and let him close the door behind him. I don’t even think I had a cell phone or anything, I wouldn’t have a smart phone until maybe age 22.
I also went to Israel that summer and wandered and hitchhiked by myself for a week and met so many people.
When I was 15, I let a friend’s 20 year old brother crash on my family’s couch for the night because he said he didn’t have anywhere to go and it was raining. This guy was in full insane clown posse outfit and was known to give free tattoos to people my age and younger. I am pretty sure he went to jail for something, if I search his name today I get the suggestion of an arrest record with a possible sexual crime. That was so dumb.
I can think of many similarly stupid teenage decisions.
I just wanted to add a lil positivity to this by saying the reason these weren’t so bad is because the men involved weren’t so bad. If you get in really bad situations with a man. It’s him if it’s not you
Errrrr…. theres been a lot 😅 walking home alone at 2am multiple times. Ive walked over 2 miles like this a couple of times.
Got into a van with a bunch of strange men. They were in a band and invited me to after party with them. The lead singer ended up trying to make out with me out of nowhere on the way but I shoved him off of me and that was that. They dropped me off at a bar.
Got drunk with a strange guy. He told me about his gun collection. I asked to see them. We went up to his apartment to look at his guns. They were cool. He kept hitting on me but in the end he was harmless and didnt try anything. My but really told me I would be OK with this one. Thats why I asked to see his guns. I like guns.
I had the brilliant idea to get drunk and go home with the hot bartender. He lived in the mountains in the middle of nowhere. I woke up in another state all confused.
Walking around alone at night. Stupid,stupid, stupid.
Several years ago I jumped on tinder in pursuit of a hookup. Matched with a guy and drove directly to his house a few hours later. No public meetup at all. It really could have been quite dangerous.
Luckily I had no weird gut feeling and had a great time.
All the times I’ve caught a ride from ppl when I was walking to work back in 2019.
Could’ve easily been kidnapped, trafficked, worse especially since I lived in a border town in an area where the SO’s were dropped off because I lived 40 miles away from a school/ playground
My ride to a football game bailed last minute and I had to drive myself downtown and then find parking. If I had known ahead of time, I would have left at least an hour earlier because parking downtown is impossible on game days.
An older man flagged me down as I was driving through a neighborhood. I stopped and rolled down my window. He asked me if I was going to the game. When I said “yes”, he said he had a parking lot on his property and he’d lead me to it. I followed him, me in my car and him leading on foot, down an alley and into a 20 or so vehicle parking lot behind a row of townhouses.
Guy was super nice. Said he loved the local football team but due to his bad back could no longer attend in person. He had all this parking available because he used to run an auto repair but was retired. I was able to get to the game on time because it was close enough to the stadium. On my way out, I shook his hand and he told me to tell my friends about his lot so they didnt have to pay for parking.
Probably wasnt the best idea to follow a stranger down an alley way. I just got good vibes from him and felt pretty confident I wasnt in danger.
When I was 19 I went over to a guy’s house and it got scary. We had hung out a couple of times, but never had sex. He was friends with another guy I was friends with and seemed nice, but turns out he wasn’t. I was not attracted to this guy and only ever hung out with him while other people were around.
One night he invited me over and told me other people were on the way. When I got there he said I was the first person there. I hung out for like 20 minutes before texting my friends and found out he had not invited them over. I got really uneasy at that point and asked one of them to call me. I acted as though it were my mom and there was an emergency with a pet. He kept trying to get me to stay and physically blocked the door (stood in front of it). I kinda just squeezed around him and left.
My friends and I kinda ghosted him after that. It was really creepy and made us all scared to be around him. As far as I know he never hurt anyone or anything, but he was very creepy nonetheless
When I was 16 years old living in Brooklyn I snuck out of my home at 1 am to smoke weed. Met a random 31 year old walking his dog and he invited me inside his house to smoke. I went inside this strangers house and smoked. Shocked I didn’t end up a dateline special. He was actually super cool and never made any moves on me. Looking back on it now I realize just how insanely dangerous that was 😭 I smoked with him a few times after that and his dog was the sweetest girl ever 💀
The first time I smoked a random hook-up’s weed…it was fine but I look back at all the variables in the context and I’m like… bruh what was I thinking
There are more than I should admit to, but one really comes to mind:
I was travelling alone in Ilha Grande, an island in Brazil. This man, who I’d briefly met the week prior at a beach on the opposite end of the island, happened across me as I was heading back to my hostel early in the morning after a blissful rainy run in the jungle. He barely spoke English and I did not speak Portuguese, but I managed to cobble together his invitation to join him on a hike back to that beach. I was in, so I had a quick breakfast and around 8 am we set off with two others joining us — a man and a woman from Argentina, neither of whom spoke much English either. We made the 8km hike in the rain. The original guy took us wading into the jungle, where he had stashed a cooler full of chips and beer as well as wetsuits — he dressed me in two layers of wetsuit, as I was wearing running shorts and a bikini top. The three of them went surfing at the beach and I thankfully knew that I could not join lol so I hung out in this hut, watching them and enjoying the sound of the rain.
While the others were still surfing, he came in to tend to the fire. We made stitled conversation and then he kissed me — I was surprised but not NOT into it lol so we made out and he went back surfing. Eventually we all started to hike back, and he kept pulling me aside to kiss me (the other two were also coupled up). I gleaned from what the others said that he was 37, had multiple kids with multiple women, and I was 22 at the time. Still, I carried on bemusedly lol. The hike went on and while we were close-ish to town, it was now nighttime and I was wet, cold, tired and FAMISHED. He tried to kiss me again while pulling out his half-flaccid dick from the leg of his wetsuit (! lol what an image) and I loudly said NO. I clearly remember him saying “Shhh! I no force, I no force!” with the other two slightly up ahead and us getting back to the hostel around 11 PM politely and without incident. Also I had pink eye lollllll
This is like, an all-time hilarious/awesome life memory, but Jesus!
Another time, also in Brazil, I was VERY drunk off free happy hour caprihanas and decided I would silently leave my group at the bar and get a cab back to the hostel I was staying at in Rio. Except I had no phone and didn’t know the name of the hostel. I found a cab, we flagged down some guy who had an iPod with internet capabilities and I managed to figure out where I was staying then made it home without incident.
One time I was in rural northern Ghana and wanted to go for a run. I found this gym some dude ran out of his house and this total stranger accompanied me on a 5k run outside of town on dirt roads. I did wear long basketball shorts to dress more modestly, but…
These and others are all great memories. But I’m a parent now, and jesus lol. I finally understand why my mom was LIVID that I was travelling alone and wanted to confiscate my passport.
Met up with random redditors. One of them we kept arguing but still wanted to meet up, and I joked to him if he’d stab me when I got into his car. We made out instead.
25 comments
When I was young and dumb I got the brilliant idea to walk from the pub to my flat alone at 1 A.M one night during Uni instead of taking a cab. I got followed by a strange man, if it hadn’t been for a very convenient policeman I was about to have to make a run for it and hope for the best.
In my early 20s, I invited guys I knew from an online forum to crash at my place while they were in town. I am 40, I still do this, made a lot of lifelong friends that way.
Hookups are always at least a little bit scary but one time when I was 20ish I woke up to the guy using my hand to pleasure himself. I was veeeery careful navigating that situation and I made it out with only one additional violation
number one is that when i was young and dumb and thought i was invincible and also drunk and on ecstasy i climbed to the top of an old water tower on the roof of an industrial building in the bronx. that still gives me shivers thinking about how lucky i was
One night stand with a guy I barely knew. Could’ve gone either way.
I was stuck in a foreign country and had to get back to the airport. A guy said he’d give me a ride in his white van with blacked out windows.
Ended up taking it. There were a total of 5 strange men in the van and me.
He kindly dropped me off at the airport.
I was driving for Uber. Had a passenger that was coming from the bar. He needed to make a couple stops and I said that was fine, they were on the way. He stopped at Walgreens for kitten food because he had just rescued some. We got talking about kittens and he asked to stop at his flower shop he owned. Yup, no problem.
He goes inside for a bit and comes out with a big bouquet. He told me he was taking them home for a friend. We get to his house. He goes to leave and then gives me the flowers and says they were actually for me. Then he asked if I wanted to go inside and see the kittens. I said sure, absolutely. I go in and hang out for almost an hour playing with the kittens and chatting some more. Suddenly, he kisses me and asks if I’ll be his girlfriend. I’m 27 at the time. This man is 55-60. I awkwardly laugh and tell him I’ll think about it and told him I had to go. He asked for my number to get ahold of me later, and I told him I had it from the Uber app. He accepted that and I left.
The next night I got a message from Uber claiming a passenger had left something in my car and needed to get ahold of me. I told Uber that that was not true and I would not be reaching out to the passenger.
I went with my ex-roommates to DragonCon one year, if you don’t know what that is it’s a huge pop culture convention in downtown Atlanta. We got into an argument and I decided to walk away from the area of the con and try to figure out a way home late at night. I’m a 4’11” and 90lb female. My ex roommates tracked me down and were like “That was so dangerous, a homeless person could’ve grabbed you and r*ped you”
When I was 12 I ran away from home with no phone and no shoes in the middle of winter. I’d wised up and started to head back when a stranger offered me a ride.
He turned out to be a nice guy and did just as he offered. I’m actually really grateful for that but it could have gone very wrong quickly.
I was in a foreign country, met a man at a bar, got in his car where he drove me to a small apartment complex to pick up some marijuana. We ended meeting up with his cousin, they had a whole conversation in a language I don’t speak. Then he drove the two of us (me and him) to a remote beach and tried to hook up. I so sketched out I asked to go back to my hotel. LUCKILY, he wasn’t a bad guy and drove me back right away. I was 20, Dumbest thing I’ve ever done
When I was 16 my guardians allowed me to drive over two hours away to meet a boyfriend I met through the internet in person. He was in fact a POS, but when I reflect on that time I think about how I could have been murdered, assaulted, etc and none of the adults in my life even cared.
Hitchhiking by myself to a club at night. I live in South Africa, this was not a good idea but I was 19 and invincible. A car full of guys stopped to pick me up and I just got in with zero fear. They were very friendly, they gave me some of the rum and coke they were drinking, and they dropped me off at the club with zero issues. One of my favourite and most irresponsible memories, lol. The 90s were wild.
Oh jesus.
Half of the situations from age 12-21 were reckless as hell.
How about this one:
I was an 18 year old census taker and had to collect the census at a trailer park in 2010.
I knock on the door and a shirtless old man with pig tail braids answers the door angrily with a cigarette in his mouth. I explain who I am and he is visibly irritated that ‘the government’ is at his door and nearly runs me off his property, but then changes his mind and invites me to come in and sit down in his living room. I come right in and sit down.
I complete his census info, which leads to a conversation about his heritage, and we actually become friends and I come visit him and sit in his back yard while he rolls cigarettes and tells me stories about the sixties and the American Indian Movement the whole summer.
He moved out of state the same summer, but I stayed in contact. He’s kind of out there and still sends me spaced out ‘one love/vaguely conspiracy theory-esque’ youtube videos through facebook messenger to this day. That was 16 years ago and I am still a fairly trusting person but I think about what that actual scene was originally, and that was pretty stupid of me to just walk in to his house and let him close the door behind him. I don’t even think I had a cell phone or anything, I wouldn’t have a smart phone until maybe age 22.
I also went to Israel that summer and wandered and hitchhiked by myself for a week and met so many people.
When I was 15, I let a friend’s 20 year old brother crash on my family’s couch for the night because he said he didn’t have anywhere to go and it was raining. This guy was in full insane clown posse outfit and was known to give free tattoos to people my age and younger. I am pretty sure he went to jail for something, if I search his name today I get the suggestion of an arrest record with a possible sexual crime. That was so dumb.
I can think of many similarly stupid teenage decisions.
I just wanted to add a lil positivity to this by saying the reason these weren’t so bad is because the men involved weren’t so bad. If you get in really bad situations with a man. It’s him if it’s not you
Errrrr…. theres been a lot 😅 walking home alone at 2am multiple times. Ive walked over 2 miles like this a couple of times.
Got into a van with a bunch of strange men. They were in a band and invited me to after party with them. The lead singer ended up trying to make out with me out of nowhere on the way but I shoved him off of me and that was that. They dropped me off at a bar.
Got drunk with a strange guy. He told me about his gun collection. I asked to see them. We went up to his apartment to look at his guns. They were cool. He kept hitting on me but in the end he was harmless and didnt try anything. My but really told me I would be OK with this one. Thats why I asked to see his guns. I like guns.
I had the brilliant idea to get drunk and go home with the hot bartender. He lived in the mountains in the middle of nowhere. I woke up in another state all confused.
Walking around alone at night. Stupid,stupid, stupid.
Several years ago I jumped on tinder in pursuit of a hookup. Matched with a guy and drove directly to his house a few hours later. No public meetup at all. It really could have been quite dangerous.
Luckily I had no weird gut feeling and had a great time.
All the times I’ve caught a ride from ppl when I was walking to work back in 2019.
Could’ve easily been kidnapped, trafficked, worse especially since I lived in a border town in an area where the SO’s were dropped off because I lived 40 miles away from a school/ playground
My ride to a football game bailed last minute and I had to drive myself downtown and then find parking. If I had known ahead of time, I would have left at least an hour earlier because parking downtown is impossible on game days.
An older man flagged me down as I was driving through a neighborhood. I stopped and rolled down my window. He asked me if I was going to the game. When I said “yes”, he said he had a parking lot on his property and he’d lead me to it. I followed him, me in my car and him leading on foot, down an alley and into a 20 or so vehicle parking lot behind a row of townhouses.
Guy was super nice. Said he loved the local football team but due to his bad back could no longer attend in person. He had all this parking available because he used to run an auto repair but was retired. I was able to get to the game on time because it was close enough to the stadium. On my way out, I shook his hand and he told me to tell my friends about his lot so they didnt have to pay for parking.
Probably wasnt the best idea to follow a stranger down an alley way. I just got good vibes from him and felt pretty confident I wasnt in danger.
When I was 19 I went over to a guy’s house and it got scary. We had hung out a couple of times, but never had sex. He was friends with another guy I was friends with and seemed nice, but turns out he wasn’t. I was not attracted to this guy and only ever hung out with him while other people were around.
One night he invited me over and told me other people were on the way. When I got there he said I was the first person there. I hung out for like 20 minutes before texting my friends and found out he had not invited them over. I got really uneasy at that point and asked one of them to call me. I acted as though it were my mom and there was an emergency with a pet. He kept trying to get me to stay and physically blocked the door (stood in front of it). I kinda just squeezed around him and left.
My friends and I kinda ghosted him after that. It was really creepy and made us all scared to be around him. As far as I know he never hurt anyone or anything, but he was very creepy nonetheless
When I was 16 years old living in Brooklyn I snuck out of my home at 1 am to smoke weed. Met a random 31 year old walking his dog and he invited me inside his house to smoke. I went inside this strangers house and smoked. Shocked I didn’t end up a dateline special. He was actually super cool and never made any moves on me. Looking back on it now I realize just how insanely dangerous that was 😭 I smoked with him a few times after that and his dog was the sweetest girl ever 💀
The first time I smoked a random hook-up’s weed…it was fine but I look back at all the variables in the context and I’m like… bruh what was I thinking
There are more than I should admit to, but one really comes to mind:
I was travelling alone in Ilha Grande, an island in Brazil. This man, who I’d briefly met the week prior at a beach on the opposite end of the island, happened across me as I was heading back to my hostel early in the morning after a blissful rainy run in the jungle. He barely spoke English and I did not speak Portuguese, but I managed to cobble together his invitation to join him on a hike back to that beach. I was in, so I had a quick breakfast and around 8 am we set off with two others joining us — a man and a woman from Argentina, neither of whom spoke much English either. We made the 8km hike in the rain. The original guy took us wading into the jungle, where he had stashed a cooler full of chips and beer as well as wetsuits — he dressed me in two layers of wetsuit, as I was wearing running shorts and a bikini top. The three of them went surfing at the beach and I thankfully knew that I could not join lol so I hung out in this hut, watching them and enjoying the sound of the rain.
While the others were still surfing, he came in to tend to the fire. We made stitled conversation and then he kissed me — I was surprised but not NOT into it lol so we made out and he went back surfing. Eventually we all started to hike back, and he kept pulling me aside to kiss me (the other two were also coupled up). I gleaned from what the others said that he was 37, had multiple kids with multiple women, and I was 22 at the time. Still, I carried on bemusedly lol. The hike went on and while we were close-ish to town, it was now nighttime and I was wet, cold, tired and FAMISHED. He tried to kiss me again while pulling out his half-flaccid dick from the leg of his wetsuit (! lol what an image) and I loudly said NO. I clearly remember him saying “Shhh! I no force, I no force!” with the other two slightly up ahead and us getting back to the hostel around 11 PM politely and without incident. Also I had pink eye lollllll
This is like, an all-time hilarious/awesome life memory, but Jesus!
Another time, also in Brazil, I was VERY drunk off free happy hour caprihanas and decided I would silently leave my group at the bar and get a cab back to the hostel I was staying at in Rio. Except I had no phone and didn’t know the name of the hostel. I found a cab, we flagged down some guy who had an iPod with internet capabilities and I managed to figure out where I was staying then made it home without incident.
One time I was in rural northern Ghana and wanted to go for a run. I found this gym some dude ran out of his house and this total stranger accompanied me on a 5k run outside of town on dirt roads. I did wear long basketball shorts to dress more modestly, but…
These and others are all great memories. But I’m a parent now, and jesus lol. I finally understand why my mom was LIVID that I was travelling alone and wanted to confiscate my passport.
Met up with random redditors. One of them we kept arguing but still wanted to meet up, and I joked to him if he’d stab me when I got into his car. We made out instead.