Quirky And Cringy: The Most Unforgettable Pick-Up Lines Ever Been Told

“First impression lasts.” That’s why people choose the sauciest lines they could ever think of in getting the attention of the people they like. But if your pick-up line sends some weird and awkward vibe, it might be the last you will see of that person.

In the world of awkward encounters, these people share the creepiest, the most cringe, and most epic lines they have ever heard. Get ready to have your 2nd hand embarrassment because these things happened! Check these out!

1. A Disturbing Encounter During Pregnancy

Once when I was very visibly pregnant a man commented on how nice my bottom looked and he asked for my number. I immediately told him I was married. He said what a lucky guy my husband was.

Then he pointed to my stomach and said, “That could have been mine.” It was the creepiest thing I ever heard in my life. Not to mention I was walking with my 4-year-old and 6-year-old daughters at the time.

missa1019

I was at a bar with one of my friends and the guy sitting next to me tapped me on the shoulder and said that the bartender accidentally gave him an extra drink and he wanted to know if I wanted it.

I told him no thanks, I have a drink. He told me he didn't want to waste his money since he was charged for it so I told him to give it to one of his friends next to him.

He then laughed and said "Why won't you take it? It's not like I'm going to take advantage of you or anything, I promise it's not roofied." We left quickly.

Bottle_rockets

The guy who confronted me in a parking garage while I was walking to my car and eating a strip of bacon who started hitting on me argued when I declined a dinner invitation and went on a long drawn-out rant.

I just stood there awkwardly eating a strip of bacon until he concluded with "Worst case scenario I buy you dinner and we never talk again and that's cool because I'd spend fifty bucks just to watch a hot girl eat a burger."

Hipmonlee

I have posted this before, but when I was 14 years old, a boy my age had his "evil alternate personality" confess to me on his behalf.

Specifically, "it" told me I was lucky that he (the boy) liked me enough to stop it (the evil personality) from ending my life.

Then he was like "Oh no, I can't believe it told you! I didn't want you to find out this way!" Yeah, me neither.

CeruleanTresses

Over winter break my freshman year in college I grew a beard and tried a new hairstyle. A girl I had talked to a few times told me "I like your facial hair," to which I replied, "Thanks, I like yours too."

My brain had decided not to work right. I thought she was saying she liked my hair and I was awkwardly trying to return the compliment. She didn't talk to me anymore after that.

wh1036

I can give you another horror story. It was this one time when I was hanging out with my friends. This guy was sitting behind me and I laughed about something that we were talking about.

All of a sudden, I just felt my hair being pulled. When we freaked out and confronted him about it, his response was unbelievable. He said he did it because he wanted me to associate my joy with him hurting me.

Martianeagle

Maybe not the worst, but certainly the weirdest. Some guy came up to me at work and started quizzing me. "What's your name?" "Do you have a boyfriend?" "Do you think I'm cute?" The direct approach.

I assume it has worked for him in the past. But then he asked if I had any kids. I said no. This seemed to derail his train of thought completely.

He said he couldn't believe it; he'd never met "a girl my age" who didn't have kids, and he kept following me around and repeating it.

"Seriously? You don't have any kids? You're not messing with me?" I escaped into the warehouse and didn't come out until I was sure he'd gone.

aciewoo

He told me he had read that book, The Game. The one that explains how to be a "pick-up artist." He told me in the same conversation in that he had been employing those strategies.

I had been feeling guilty about not giving the guy a chance even though he creeped me out and I had no interest in him whatsoever. When he told me that, it all made sense, and I noped right out of there.

[deleted]

One guy in his 40s saw me at my grandparent's house and decided to try complimenting me by complimenting my kid and how polite he was.

When he was informed that that kid was my brother and I was 12, he doubled down, arguing that 12 was a perfect age to have kids and progressively got creepier until I bolted back in the house.

But most recently I had a guy go on a two-hour rant about feminism and the smash bros scene (I did not ask for this topic of conversation, he 100% brought it up.)

I might've appreciated the effort/point he was trying to make (that he respected women) if he hadn't interrupted me every time I tried to talk.

He blatantly talked over me several times and ignored pretty much anything I said, including numerous attempts to turn the topic of conversation to anything else.

It was honestly impressive how he managed to go on this massive, completely random "I respect women!" rant while blatantly disrespecting me.

royallyred

I had an experience along that line before. My friend was going through a bad time so I took her out to try to cheer her up.

This guy comes up to our table and goes into this long speech about how much he respects women and "he loves his mother" (he said this like 50 times) and on and on and on about how respectful he is.

He is also saying that if we didn't want him bothering us just say so and he would leave us alone.

When he was done, I politely replied how refreshing it was to hear a man say that and we appreciate that, but we were having a very private conversation (like I said she was going through some crap) and we didn't want company.

He looked at us very confused for a moment, then started his speech all over again. It was the same speech almost word for word.

My friend and I are glancing at each other. He even ended the speech with the same "Tell me to go and I'll leave you alone." I replied, “Okay We want to be left alone”

But he was still confused: Then he said, “But, but, I love my mama” (I swear to you, he said that). At that moment, I was already aggravated, ” Look, dude, I said go away.” Then he got mad and called us the nasty B word.

He goes into a loud tirade about what awful wenches we were and how nice and respectful he had been to us.

He finally leaves us and goes back to his friends. But he keeps yelling nastiness across the bar at us while I hurriedly down my drink, and we get the hell out of there.

leftbyfairies

One man said to me, “You know, your pockets are hanging out of your shorts. That's usually pretty provocative, but I like that" I was with a few friends, and one of them told him to get lost as I turned around to ignore him.

Another was a time I worked at a grocery store. It happened twice when I came out to my car with a note.

The first time the first note stated that I'm very beautiful and he'd love to take me to coffee, but he has a wife so it'd have to be a secret.

The second note told me where to meet him for coffee. Super creeped out and didn't walk to my car alone for quite some time. Never figured out who it was or how they knew which vehicle was mine.

Holliepoppin

He told me that we were destined to be together because, in several previous lifetimes, we'd been teen lesbian lovers in an alternate universe where anime was real.

He insisted on calling me by my "true name" (the name of some anime character he liked) and he would even "correct" my school papers with the "true name."

He had a notebook full of stories and drawings about our future life together, and he'd picked out names for our children and designed my wedding dress. This was all after we'd talked to each other casually a few times in class.

Shinkouhyou

I was at a company party back around 1990, at the VP of Operations house. The entire company was there. Very young crowd, average around 25.

One of the VP's assistants gets drunk and manages to fall into the pool fully dressed. He gets out of the pool, loses all his clothes, and is now walking around in just a towel.

Liz, a barmaid that we all knew, had been invited. She's playing pool in the pool room and this guy walks up as she's bending over to line up a shot, opens his towel, flashes her, and asks her, "Do you know what this is?"

I should mention that Liz wears glasses. She squints over the top of her glasses, shrugs, and says, "Well, it sort of looks like a pee pee only smaller." We all chipped in for the tombstone.

dramboxf

My boyfriend passed away in a car wreck by a drunk driver one year ago. He had to be cremated. I am in college, and at the time I was walking across campus when his mother texted me that the cremation had been done.

I fell to the ground in tears. A guy picked me up off the ground and hugged me. I just cried into his shoulder and told him what had just happened, saying something like "My boyfriend died." He said, "Well, do you want a new one?"

cactusflowercorpse

I told a guy I was once talking with I'm a disease major. He asked what my favorite was. I said, "Oh I loved studying smallpox." He replies "Well no, it was awful."

Then all of a sudden, he started explaining how it spread and all the symptoms of an illness. He was actually talking about the bubonic plague.

SpaceAgeUnicorn

This was a pickup line and I do have to admit I got a chuckle out of it. A man from Ireland with a thick Irish accent was chatting my friend and me up.

He asked us about ourselves and what our backgrounds were to which I responded: "I have a little Irish in me." He responded: "Would you like a little more?" We laughed, hard.

kristenlilian92

I may have been someone's worst line. The girl says, "Nice jacket.” It was a pretty cool cotton velvet jacket and that was a great way to open a conversation with a compliment.

I turn to her and instead of smiling and chatting her up like a normal person, out of my happy mouth comes, “Thanks! A boy had to love fifteen velveteen rabbits to make it!”

_Neoshade_

While I'm sitting at a big table with several close female friends all of whom can hear him, "You're the most attractive woman here. Everyone else is so plain. They're not even trying and some of them are so overweight."

I mean he was drunk but still, such a douche. It was not a venue, like a club or bar, where anyone was making a big effort. It was a nerd con. No one was there to pick up dudes.

deadgloves

It was my first college party, I was hanging out by the fire and this guy came over and was talking to me. The next thing I knew, he looked at my chest and said "C or D?"

I turned away fast from him and told him It was none of his business. What a creep!

vandorengirl

I had a Nice Guy tm problem a few years ago. After rejecting his advances multiple times over the course of 6 months, he completely switched.

He said something along the lines of “I don't date wenches anyway! You're nothing special and this is your loss, I would've been the best thing to ever happen to you!” He then went on to write a song about me dying. He was a musician.

InvaderNugget

When I worked at a toy store, we had to start every single transaction by asking for the customer's phone number.

The number of middle to late-aged guys who would be with their kids and say something like "Oh, you gonna call me later, baby?" in a super creepy voice was astoundingly high.

I also went on a date with a guy from a dating app who spent the first 30 minutes talking about his running, then turned to me after talking.

He then asked me, "So, what do you do? You're clearly not a runner, but you're not too fat, so what do you do?" That was the first question he asked me. Not off to a great start, dude!

rubberduck05

The man who said it wasn't the one trying to hit on me, he was trying to set me up with his son. I work in retail, he was a customer.

This guy said "You're quite a nice-looking young woman, you know. I have a very handsome son who is due to come back from the army in two weeks. I'll set up a meeting, shall I?"

I declined as politely as possible because I'm with someone and I don't want to be set up with random dudes. He suddenly turned quite nasty.

He started to question me why I wouldn't want to date his son and if I didn't I hear him properly. He also said he was a soldier. He asked if he had mentioned how very handsome he was and what was wrong with me.

Said no thank you again and then he started belittling me for my job and said "It's not like someone in your position could ever hope to do better. You should be grateful for this chance!"

I dearly wanted to say "Well if the son is anything like the father, I most certainly don't want to meet him" but eh, couldn't get written up for being rude to a customer.

[deleted]

I was sitting on a bus with a friend and a man started talking small with me (he was maybe in his late 30s or 40s and I was 20).

He keeps asking me questions in a foreign language and I just keep shrugging but he keeps talking and not taking hints that I'm trying to end the conversation so I just end up turning away from him and ignoring him.

He grabbed my purse and I thought he was trying to steal it, but it turns out he just wanted me to pay attention to him!

As soon as I look at him he starts talking to me again! So I told him to leave me alone and he started cursing and yelling, and when I got up to move seats he kicked me.

not_homestuck

A man once told me, "You're pretty, for a black girl." Like what? For a black girl? Is there a tier of pretty that is barred from me forever due to my race? Did you expect me to be ugly because of my race?

Why can't I just be full-stop pretty? Adding the "for a black girl" part entirely negates the compliment and after being told this, I can never conceive of that person being more than an acquaintance.

iPwn__

He was a very nice and attractive guy and obviously knew that but I was waiting outside for my cab and he started talking to me and then reached over and said "I don't think you'll be needing that" and cancelled the cab I booked.

I said hello to the cancellation fee! This royally pissed me off and caused me to get in the wrong cab because I was flustered, but luckily the guy was super nice and took me home for free.

amberjean23

When I was walking across the parking lot at work, a guy approached me and asked if I wanted to fool around. When I turned him down, he was persistent. I pointed out it was the middle of a workday, he didn't care.

I lied and said I was married, he told me that my fake husband wouldn't have to find out. I lied again and told him I was 6 months pregnant (it was winter and I was wearing a big coat).

Then he said, "Perfect, then I don't have to use protection and I won't knock you up." And all the times that I've been out and guys that I don't know will just pick me up and carry me away.

Like away from the people I am there with. I have no clue why they think that would work on anyone.

TA704

I wasn't hitting on her, and this one is me. I was out on a smoke break at my old job, and I was getting to know a new female employee. She has her hair dyed bright red and black. "I like your hair," I said.

"Thanks" she replies, rather bored and uninterested. I tried to make up for being awkward by being funny and said "If we were in the jungle your hair would say I'm poisonous, don't eat me."

She gave me an incredibly baffled look and burst out laughing. At least she had a good sense of humour.

Owwmysoul

I was having a drink with a work colleague before a gig. She's 20, I'm 32. A guy comes up to me and starts trying to flirt. One of his first questions is "So, are you her mum?" Not entirely sure how he thought that was going to work.

Later that night, same pub but this time after the gig. Another guy starts trying to flirt with me, after his opening statement to me about how he thought my friend was "Freaking gorgeous." Guess it was just my lucky night.

taste_the_sunrise

It was my first week working at my current job, and I was on the sales floor stocking (it's a massive store) and some neckbeard douche wouldn't leave me alone.

We for some reason got on the topic of knives, so I told him that they were my biggest fear. He then proceeded to say, "Oh, you don't like knives, huh?"

All of a sudden, he flicked open a pocket knife an inch away from my face, laughed, and asked for my number.

lil-yahtzee

After telling a guy I was getting a Ph.D. in engineering, he said, "No, I don't believe you, you're too pretty for that.” I'm bi and have heard this line from 3 guys and zero women.

Also, the ex-coworker asked me over a job application to be his date to a wedding in another state after we hadn't seen each other for 2 years.

We had barely interacted at our previous shared job. He ended the email by reassuring me that he was single and that it didn't need to be a platonic wedding date.

lettuceeee

Once when I was walking downtown with my boyfriend a guy came up to me and asked if I had a twin or a sister and I said no.

He said that was too bad because he had a bunch of land and property and was looking for a wife, and if I had a twin or a sister he would marry them. It was pretty obvious he wanted me, but since my boyfriend was there I was taken.

The second one happened this weekend. I was waiting in line for some late-night pizza and this guy and his friend who were next to me in line started chatting with me.

The drunker of the two compliments the dress that I was wearing and asks if I think he would look good in a dress like that.

I tell him sure, and he then suggests that we go into the bathroom and switch outfits. It was a pretty clever way to try to get me naked, but I had to decline. His friend later apologized to him.

how_about_lefse

There is this man who said to me, "You're cool, not like the other females around here. I was just trying to talk to one and she went to campus security saying I was stalking."

He was creepy and I was always trying hard to brush him off. Avoided him and got a social media message saying "We could have been done and over if you weren't such a douche" when I was constantly bringing up my boyfriend.

[deleted]

I was in a train station by myself (I was 17 at the time) and a random guy (about 45 years old) came up to me and said "Hey you waiting for your boyfriend?” I answered, "No I'm waiting for my friends."

He sits next to me in silence looking at his phone as I wait for my friends and then he says. "You’re so pretty in this picture" and then shows me random pictures of myself on his phone taken on different days.

MrsG1991

Not me, but a friend, let's call her Anna. Not her real name. In high school, we were at a bonfire/party one night. Anna was new to our school at that point, so our friend group invited her.

It was a general thing with around 20 kids, about half our graduating class. So everything is going great. We're in some wooded area behind the host's parents' house and the beach was about a ten-minute walk.

It's a pretty safe area, with lots of well-worn trails and people, but of course, Anna didn't know that. Anyway, this kinda weird but harmless kid, Nathan, introduces himself and asks her if she wants a drink.

She takes it, and they chat. He's flirting with her. She's polite and engaged but not interested. Finally, there's a pause in their convo. He's run out of topics.

So, he blurts out "Do you wanna go for a walk in the woods? No one is there right now so we can talk away from the party as long as we want to." She said no and noped out of that convo super quick.

[deleted]

Not a woman but this happened two weeks ago while I was out drinking with women: Now we have these two fairly attractive girls at our table (coworkers) and we're talking, and having fun.

We're all like 20 to 24 years old. A guy, around 28 to 32 years old asks for directions to probably one of the best-known spots in Cologne (Zülpicher Platz). He asks one of the girls and does it just to be able to talk to her.

She instantly knows what's going on and tells him "Well just out, straight ahead, left right and you're there" all while laughing. He thanks her and goes outside, where more men await him.

We see him pointing at our table, grinning. Another guy comes in and asks the same girl for directions to the same place. She laughs again and tells him the crap directions again.

He thanks her and wants to high-five her. She, being an absolute badass, stares into his eyes and ignores his hand.

Like Barney Stinson, he turns to the next person (the other girl) and looks at her, she ignores him too. My buddy and I are losing our minds at this point, the guy looks so devastated and finally turns to us.

Being the good guys we finally free and high-fived him after his hand was up for what felt like 2 minutes. He goes out, pretty ashamed and they take off.

IqfishLP

I was in the grocery store strategically picking out a potato salad with the most potatoes in it when a guy walked up behind me and said, "I don't know what you're doing in the gym, but it's working for you"

There are 2 things about me, one is don't distract myself when I'm focused on my potatoes. Two is, don't let the workout pants fool you, my dude.

These are comfy leggings and I'm going to eat this whole sub and potato salad then play video games all night.

lkcoyne

I am not a girl, but I thought I'd share because this happened 3 days ago. This guy came up to my girlfriend at her friend's birthday party.

He attempted to flirt with her. He basically just told her he wanted to fool around with her and she should go home with him.

Yes, he was that blunt to actually ask him that. She didn't say anything, just walked away.

[deleted]

When I was 16 or 17, a man sat next to me on a bench while I was waiting for my bus to arrive. He asked me how to get somewhere specific using our public transit system and I explained to him the best I could.

He then proceeded to ask for my number and I told him I didn't have a phone, only a tablet (which was true at the time). He still gave me his number which I wrote down out of fear and he continued to make small talk with me.

My bus thankfully arrived and I told him I had to go. He then proceeded to say, "Wait, I can drive you home. My car is parked just right there."

The first thought that came to mind was, "What the heck, this guy just asked me which bus he's supposed to get on?"

Then it hit me that he was probably trying to abduct me. I ran onto my bus and feared he was following me my whole ride home.

_whitepeaches

Maybe not the worst pick-up line, but probably the most recent one I had encountered. I had this guy asking about my hobbies. One of the things I spend a lot of time doing is hanging out at my local aquarium. It's my relaxing place.

And I told this guy that, and he immediately said "Oh wow, boring.” And then proceeded to ask me for coffee and my number. Yeah, no thanks.

RoxyBuckets

I worked as a night clerk at a store during college, which is something that no daughters of mine will ever do. One of our regular guests, who was known for being frisky, bought a can of orange juice from the vending machine,

He took it back up to his room, called me on the front desk phone, and read me the description of the orange juice printed on the side of the can in a sensuous tone. I was 20 and he had to be at least 50, the lousy pig.

Maybe the orange juice thing made some sense when he was reading about the perfectly ripe and sweet fruit making delicious juice but not when he got into the parts about it being a good source of vitamin C and potassium.

As far as we could tell, he was a successful businessman and family man. He must be at least 75 years old now, the filthy lecher.

MrsTurtlebones

One time, I was on the assisted pull-up machine at the gym. A guy walks over and talks to me while I work out with my headphones in, "You could do a pull-up without the weights helping you come on."

I answered him, "I really can't, I've tried." Then he responded, "Nah, you're being lazy. You must look good just because you're Asian."

Wish I had known sooner that I was wasting three years of my life lifting weights when all I had to do was just be Asian. This was at the gym, so there was no alcohol involved, just pure, sober douchery.

bolognaaaa4

I've had a couple of guys try negging. One very pointedly told me that he liked girls who were chubby or had a tummy.

Another just awkwardly pointed out that I had bunions at the ripe old age of 14. Both of those were things I was very self-conscious about when they were pointed out so that sucked as a strategy.

I had one guy do the whole "white knight turned douche" thing. He was a nice guy for a whole year and seemed kind of protective, even in situations that didn't call for it.

Apparently, he got tired of that and the next year he wouldn't stop "jokingly" calling me the nasty B word until I just stopped talking to him at all.

The weirdest one was this guy I dated for a couple of weeks. He texted me "My water worm likes to swim.”

When I asked him what exactly that was supposed to mean he just said, "I don't know." I assumed it was an allusion to physical intimacy, but the world will never find out.

Boatkicker

I had poison ivy and had to go get a steroid shot at a medical center. The nurse was a young guy, and I didn't realize he would be the one giving me a shot. I also didn't know it was in my rear end.

When he told me it was in my lower hip, I must have been surprised because he proceeded to give me my shot as he said "Don't worry, at least you know my name before you drop your pants." I was honestly mortified.

HopeM2013

I was out in Atlanta at a comic conference with my wife and her friend. We were cosplaying as Ranma and Shampoo from Ranma 1/2, and I can't remember what the friend was.

All of a sudden this car full of dudes pulled up beside us and said, "What are you all dressed up for?" We replied Dragon Con, and the driver replied, "You one fine dragon" and pulled away. It was the funniest street harassment ever.

Madaspy

A guy once told me, "You understand that I'm a lot smarter than you because I'm a guy, right?" I laughed and laughed. This was not well received.

He called me all sorts of insulting words until I caught the eye of the bartender and suggested this man tab out immediately.

The bartender recognized the situation and tabbed him out. My final words to this douche nozzle were "You should have a shot for the road, then drive. Don't forget to tip him well."

ritarue