Sometimes in conversation, the filter doesn’t kick in and we say something that we immediately regret. These AskReddit users share conversations that got creepy and awkward real quick.
Sit back, relax, read, and enjoy the creepster cringes below.
1. Sexy Tank Top
I worked at a summer camp. There was an 11 year old female camper who had a tank top that said “sexy” on it.
On our time-off all the counsellors were hanging out and talking about inappropriate things campers would say/do. I tried to join in the conversation by saying “Did you guys see the girl with the sexy tank top?”
Just as I said that another counsellor had walked into the group and exclaimed “What is wrong with you? She’s like 11!”
2. Well, okay then…
Very nice grocery store cashier told me she hoped I have a wonderful day. I have no idea what possessed me to respond with a friendly, “thank you, I hope you never die.” She was probably scared to walk to her car that night.
This story is legendary among my friends. In an elevator with my wife, who is petite while I am tall. Gentleman gets in and after some small talk asks, “And is this your daughter?” For reasons still unknown and, to this day, I still question myself about, I enthusiastically responded, “I wish!”
After one floor of dead silence, I mumbled, “I don’t think that came out right…” and the gentleman just mumbled, “Yeah, mm-hmm” and promptly got off on the next floor.
4. The Squirrel Whisperer
I go to a school with squirrels all over the place. One day I’m walking and I see there is a squirrel like a foot from me. I whisper, “I’m so close to you,” smiling at it, and a lady I had not previously noticed turned around and gave me the most upset and scared look while she got walked away from me.
5. Not a good idea.
Male, and I normally wear boxer underwear. But as it happened, one night out at clubs, I happened to be wearing some distinctively patterned briefs that I’d received as a Christmas gift. Standing on the sidewalk at closing I catch a glimpse of a girl in white pants, and the light is such that I can see the print on her panties. Lo and behold, it’s the same as the one’s I am wearing. Thinking this gives us an instant connection, I start towards her yelling, “hey, check it out,” while unzipping my pants…
6. Baby = Headache
I was hanging out with some friends, and one couple had a crying baby. It was giving me a headache, so when it suddenly stopped crying, I mumbled in what must’ve been a super creepy voice, “Oh yeah, that’s nice.” Everyone else got silent, so I looked up. The baby was breast feeding.
7. Straight When Sober?
One time I got blacked out at a college party my junior year. Didn’t happen very often since I wasn’t a big drinker, but hey, gotta let loose sometimes.
The next morning, my roommate is giving me weird looks all day. I ask my girlfriend at the time “What happened last night? Justin has been giving me cold stares all day.”
Apparently, after the party, we went back to our apartment to smoke and I decided to coach my roommate’s girlfriend on how to give better blowjobs to her man. Because I’m a true bro. My friend deserves the very best fellatio. Complete with details on how to control lip muscles and tongue movements.
I’m straight, at least when I’m sober.
8. It’s a hard job.
I suddenly yelled “You all are making me hard!” to a class of high school students when I was a student teacher. What I had actually meant to say is something like “You all are making this hard to do.” Yeah… I didn’t really live that one down. Every time I asked certain students to do something they would say “Ok, Mr. XX, I certainly wouldn’t want to make you hard again.”
9. $5 Ambition
This happened way back when I was about 14. I went to the movies with a couple friends, and this cute girl about my age came up and said “If I give you a hug, will you give me a quarter?” pointing to the gumball/tiny toy machines. I reach in my pocket and realize all I have is a $5 bill, so I say “What do I get for $5?” Yeah, did NOT think that one through. First time I ever got slapped by a girl…
10. Wrong Food Group
I was at the university, and some girls were out in the grass in bikinis trying to get a tan. My friend says “Damn, those girls look great.” I look over, and think they really aren’t to my taste. Just down the street were some people passing out hotdogs for student elections. I get sidetracked and say “They’d probably taste great with some mustard.” Whoops.
11. Sweaty Wishes
There’s a gas station behind the restaurant I work at. So, one day, whilst on break, I walked over and bought a bunch of snacky items and a couple scratch offs.
On my way out, a girl bumps into me, and I dropped my items. She’s wearing nothing but a sports bra and running shorts, she’s also covered in sweat. I’m assuming she just finished jogging.
She’s apologizing profusely, and I don’t want her to feel bad, so I just say “Hey, don’t worry, it happens all the time.”
“Sweaty girls bump into you all the time?” she asks. Without thinking, I say “Oh god, I wish.”.
She turned red, apologized, and left.
12. Comparing Caves
My friend was speaking with a young hostess at work about how cold their basements were. He had just put in a space heater and was calling it his man-cave as he was explaining his new set up. He then proceeded to ask the girl how her “woman cave” was, if it was warm and moist like his is.
Needless to say, they won’t make eye contact anymore.
13. Larger Than Normal
I bartend on the weekends at a major chain restaurant. The POS stations (the computers where we plug all the orders in) won’t allow credit card tips over 30% without manager approval. They need to swipe a card to make it work. So it was the end of the night, just me and my manager behind the bar, and I say to him, “Can you help me put this tip in, it’s too big to enter.”
14. Not hers though!
Not me but my little brother (he was 12). We Were at a restaurant and he wanted to order the “seasonal fruit.” We were discussing what we thought was in season that time of the year, and he just went ahead and ordered it without asking. When the waitress (wearing a low-cut shirt) brings the plate and it has cantaloupe on it, she leans over to put it on the table and my little brother says “Oh, I see MELONS are in season.” We were laughing too hard to apologize.
15. Death Wish
Was driving back from a first date with a girl. Went poorly; I was even more shy, nervous, and awkward back then. We’re driving through an area with lots of plains, not a car in sight for miles. Gas is starting to run low and I decide we should head for a gas station.
And then I blurted out, “Man, we could both die out here and nobody would ever find our bodies.” She looked horrified for a few seconds. I then realized “Oh man…we should find a gas station” was something I didn’t say out loud before that; I just thought it in my mind. I stumbled towards explaining what I actually meant by that morbid comment. Needless to say, the rest of the trip was kinda quiet and weird.
16. Spread Eagle
I’m a preschool teacher. As I was leading my class down to the indoor playroom a couple weeks ago a child asked where we were going. I said “To the climber. It’s nice to spread our legs!” which didn’t seem quite right to me, though I couldn’t figure out why. I also noticed another teacher giving me a weird look.
Later, I realized I meant to say “stretch our legs” and felt pretty embarrassed and creepy for the rest of the day.
17. Milk Jugs
I worked at a cafe/bistro in Kona, Hawaii when I was an awkward 19 year old as a dishwasher, but when it was slow, they would send the servers home and I’d walk orders out to tables. One day this lady was breastfeeding her kid in full view at her table and I was the only one available to take her drink out to her, so I take her coffee out to her. I end up spilling a small carafe of milk at her table. SUPER! So, I had to come back out to clean up the milk mess and be more awkward and I was trying to make small talk, so this came out of my mouth — “I can’t believe how much milk those little things can hold!”
Yeah, I actually said that. Her jaw dropped and I just walked back inside and sat in the employee bathroom on the toilet for like half an hour with a really, really hot face just replaying the moment over and over in my head. My face still gets hot with embarrassment just thinking about it.
18. You’ve been creamed.
I was at brunch in the cafeteria at my college sitting with a group of friends. I got a cup of coffee, which I usually took black, except for the one at that cafeteria, because it was so terrible that you needed to add something to make it drinkable. I sat down I tried to pour a little bit of creamer, but ended up overdoing it and it spilled onto my lap. That’s when I loudly said, “Oh my God, I just creamed my pants!” My friends all looked at me for a second and then laughed when they realized what had happened.
19. Yes, it did sound creepy.
Not me, but my uncle. We were at the gym, and these younger kids, probably 12 to 13, were running on the treadmills. My uncle, glad to see that these kids are exercising instead of just sitting around, turns to me and blurts “Y’know, I really like watching young kids work out!” It took him a minute to realize why that sounded creepy.
20. Cringe Worthy
I did this one. Important to know I’m a dancer and I love doing swing style lifts. Waiting for someone, I noticed a young girl, probably 14 or 15, across the way. She was close to 6′ and very thin. Thin partners are amazing for lifts, pretty much all options are available. So I must have been out of it and I just started day dreaming about all the dances we could do.
So here’s a guy in his late 20’s openly staring at a 14-year-old girl. She caught me and said “Is there something you need?” And I don’t know why these words came out of my mouth, but I just grin and say, “I could just throw you around.” She looked quite shocked and hurried away.
One of those moments in life you relive a thousand times and cringe each time.
21. Didn’t realize it was a guy until the end.
I was on vacation at a nice lakeside hotel. Once we arrived we went straight to the “yacht club” area; a man-made beach/pool area on the lake. It was right before the poolside bar closed so we wanted to get as many drinks as we could for the hour that was left. I walk up and order my drinks and joked with the bar tenders that I was trying to get smashed quickly. They reminded me they were only open for another hour and I said: “Oh don’t worry, I’ll suck you all dry before then.”
Was referencing the alcohol but it kind of came across as creepy. I’m straight, they’re straight, it was awkward.
22. Taking Halloween a bit too serious, bud.
At a Halloween party dressed up as the Red soldier from TF2. Girl comes up to me and asks me what I am. “I’m a soldier.” She is obviously flirting and says “Aren’t soldiers supposed to be dressed in camouflage?” I say “The red helps me be camouflage in blood.” She walked away quickly. facepalm
23. In the Zone
A couple of years ago, I was out jogging one evening in a local park. Like most, I had my mp3 playing high tempo fast pace songs. Part of the circuit passes though a very quiet section with no street lights, and is pitch black apart from starlight. I was running through this section and was making good pace, endorphins flowing, feeling that runners high, when the song Gay Bar by Electric Six comes on. As I’m elated, I start singing along, then as I’m singing the “IVE GOT SOMETHING TO PUT IN YOU, I’VE GOT SOMETHING TO PUT IN YOU” part, two girls emerge on the path and start screaming.
I cringe when I think what it must have been like from their point of view. A big hairy sweaty man running towards them in a dark park, shouting “IVE GOT SOMETHING TO PUT IN YOU.”
24. No, it didn’t play out that way.
So I was in a meeting with a large group of people that I had never met before and as a part of the “ice breaker” we each had to say our names and something about our selves. Two people before me is a lady who owned all or the extended edition Lord of the Rings movies and watched them all regularly. Next was another young lady who’s interesting thing was that she had never seen any of the Lord of the Rings movies despite trying on several occasions. Now, I don’t know what made my brain give the green light on this but I stood up, said my name, and look the girl next to me straight in the eyes as I said, “I have 3 rolls of duct tape and a DVD player. We’re going to have a great night.” I meant to mean that we would watch the movies together and if she got sleepy she could try to tape her eyes open. Didn’t play out that way.
25. I’m disappointed by the employee.
I was at PetsMart with my girlfriend. I walked around while she shopped for “dog christmas presents” and I looked at the fish and the small animals. In one area of the store, there are cages that contain guinea pigs, some of which are fluffy with long hair and look cuddly. There was a young lady with shoulder length blonde hair looking intently at one of the guinea pigs. My girlfriend had the exact same haircut. I came up behind her, put my face kind of beside her head and above her shoulder and said in a whisper, “they look so soft…” (in reference to the guinea pig). At the same time I rested my hand on her hip, pretty low towards the butt area.
Of course it wasn’t her, it was some college girl looking at guinea pigs.
The worst part is that I realized when I touched her that it wasn’t my girlfriend and consequently let out a this shaky gasp of shock and horror directly into her ear, like I was breathing on it. She whipped around and started to say something to me but stopped and just ran out of the store when she saw who it was. I had a full beard. There was an employee like 5 feet away who saw the whole thing and did absolutely nothing.
26. Verbal Diarrhea
A female friend of mine – to whom I was admittedly attracted – had been expressing her reservations about an upcoming vacation with her family. Though it wasn’t being overtly presented as such, the trip was meant as a way of re-solidifying her parents’ marriage, which had been a touch rocky at the time. They would all be driving from San Francisco to Redding (which is a small town in the middle of absolutely nowhere in Northern California), where they’d stay at a bed-and-breakfast inn for a weekend before continuing northward for some unknown destination.
In keeping with the alleged purpose of this so-called vacation, my friend’s parents had booked two rooms at the inn. To her dismay, though, my friend discovered that her mother would be occupying one room, her father would have the other, and that she and her sister would each have to bunk with one of their parents. This was worthy of lament on its own, but it was made unforgivably worse by the verbal diarrhea that I offered in an attempt at providing comfort:
“Aw, it won’t be so bad!” I told my friend. “Your father will probably enjoy sleeping with you.”
A moment passed before I realized what I had said. Then, with a feeling of growing horror, I tried to explain myself. “Wait, I didn’t mean it like that!” I hurriedly said. “I mean, like, he’s probably sick of sleeping with your mom. No, wait, I mean… I just mean that he wants to spend some quality time with his daughter.”
If I had stopped there, I might have been able to salvage the situation… but as it happened, I decided that the best course of action would be to keep talking. “I can’t say that I blame him, really. I’d love to sleep with you.”
She and I don’t talk much these days.
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