February 4, 2021 | Scott Mazza

Swing And A Miss: These Pick-Up Attempts Failed Miserably

It’s excruciatingly hard to tell someone you like them. You might be the coolest cat around, but the moment you approach a person you’d like to date, your heart might start racing faster, your palms might start sweating, and your brain just seemingly turns to mush. That said, your dad’s worst jokey one-liner has nothing on these mortifying pick-up fails. 

1. The Escape Plan

A friend of a friend came to a bar a bunch of my buds used to frequent, and from the get-go, it was obvious she wanted to leave with someone. That would have been cool with any of us, but there was one big issue. She was loud and obnoxious with an extreme air of desperation about her, and all the guys could smell it and stay far away. I myself was there just to drink a pint and hang out.

However, I'm apparently too nice, and before I knew it, her sights were set on me. Whenever we were in proximity to each other, she tried to talk to me, or touch me, or laugh at every word I uttered. At one point, she hugged me and said, "My God, you smell gorgeous!" and then proceeded to continue to smell my neck for a few minutes as I semi-resigned myself to be devoured by this annoying girl.

While I was trying to desperately figure out a way to eject from that plane wreck, she said something like, "Wow, you're dressed so well, are you trying to impress us ladies?" That caught me off0guard, so I paused. Before I could say something, she continued with "...or someone else other than ladies...?" in a really playful tone. Before I knew it, my brain went instantly into action. 

Suddenly, I was telling her I played for the other team. A total lie, but it worked. 

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2. Sugar And Spice

My parents were walking through Target when this stumpy guy walked up to my mom. He kept saying: "Sugar zero, sugar zero, sugar zero." My mom laughed and asked him what he meant. The guy replied, "If anybody asks, you can tell them that I whispered sweet nothings to you." My dad was laughing too hard to even care about the attempt. 

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3. Switching Sides

When I’m drinking, I always seem to get hit on by lesbians. I always have a very good time with it too, and I've gotten a few numbers...but it's not like I was trying to convert them or something. I always wake up the next morning wondering what the heck I was trying to pull. I made a few good friends that way though, at least. 

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4. Too Young For You

I was walking down the street with my mother. As it was summertime, I was in shorts and platform sandals, which were in fashion at the time. I walked by two guys. One of them started saying that he loved me and wanted to go out with me. My mom asked him if he was crazy, to which he replied, "I'm crazy for her." I was nine. 

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5. Textbook Creep

Last summer, I spent three months selling educational materials door-to-door. It was handbooks and software and such. Since these materials were designed for kids aged three years old and up, I talked to a lot of parents. Now, the company who I worked for as an independent contractor had trained us not to go into a house unless we could physically see the mom. 

We all followed this rule. Strictly. But halfway through the summer, I approached a door and the dad answered. I thought that I heard the mom inside the house, so I assumed it was safe to go in... It turned out, I was hearing the TV. It was way creepier than I even expected. It's really awkward when a guy, a father, who is twice your age, hits on you. 

Especially when you're there to talk to him about his kid's education. His exact words were, "You have very nice legs, do you play soccer?" and he put his hand on my thigh. Needless to say, I got out quickly.

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6. Tag Team

So I witnessed this at a college bar in California. This young couple was sitting together at the table next to mine and it was apparent that they were dating—they were holding hands, smiling at each other constantly, etc. They were minding their own business when out of nowhere, a guy in his early 20s walked up to their table.

He looked at the girl for a second, then glanced at the guy, and said: "Hey guy! Mind if I talk to your sister?!" Well, hearing this, I looked over at the boyfriend and he had this look on his face that just screamed, “What the heck??” So here's how the rest of the conversation went...

Boyfriend: “She's my girlfriend man, so yeah I mind.”

Guy: “You're dating your sister? Gross.”

B: “No, she's not my sister, she's my girlfriend.”

G: “Ohhhhh. So she was your sister...and now she's your girlfriend?”

B: “No, leave us alone kid.” At this point, the guy turns around and yells for his friend to come over.

G: “Hey!!! Come over here! This guy is dating his sister!!!”

The next thing I knew, this well-groomed and well-dressed guy came over to the table to see what kind of trouble his buddy was getting into.

Guy: “He's dating his freaking sister!” 

Guy 2: “Isn't that against the law?” At this point, the couple was pretty angry and the girl suggested to her boyfriend that they go somewhere else. 

As they gathered their things and started to walk away, the second guy walked up to the girl and said, "Hey, would you mind if I talk to your brother?" And this look of horror spread across her face as she realized this gay man wanted to talk to her boyfriend. The couple basically ran out of the bar and the two guys busted up laughing from the reaction they got.

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7. Caffeine Kick

I was walking back to my car one night and a group of young guys was hanging out on the sidewalk, taking up most of its width. My friend and I had to walk through their group. As we did so, a guy stepped in really close to me and whispered, "Girl, I'll buy you Starbucks every night." I had no idea how to respond, so I just smiled and kept walking. 

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8. A Hairy Situation

I have very, very long hair. It reaches below my knees. If it helps for visualization purposes, I'm a slim Asian female. "DANG, GIRL! Your hair is crazy! Like a horse tail! Hey, you should know I'm a total stallion, babe." This guy leaned in really close and started stroking it. I got the heck out of there as fast as I could. He called after me in a gruff plea: "Aw, c'mon, girl, lemme see if all your hair is long and beautiful."

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9. Just Keep Swimming

Let me start my story by saying that I am very, very pregnant. I am so hugely and obviously pregnant that people feel the need to approach me in public to offer their condolences for how pregnant I am. I am not kidding. Men and women alike have stopped me just to say, "You poor thing…I am so sorry. You look miserable." 

That is how pregnant I happen to be at the moment. That said, my favorite place to be in the entire world is in a pool. Swimming makes me feel like a normal human being. The swelling in my hands and feet goes down, the pressure on my hips vanishes, my belly button goes back to being an innie…It's wonderful. But I soon regretted this habit.

Last weekend, my friend texted me and asked if I was up for a swim. I certainly was up for a swim; however, it was a little after 8:30, and my condo's pool closed at 9:00. We decided to go to the pool at her apartment complex, as it was open until 10. We made our way out to the pool, where the only occupant was a middle-aged guy wearing a swim cap and goggles. 

I didn't pay him any mind, since I just figured it was a resident doing some evening laps. No big deal. He watched us get in the pool and then said something I couldn't make out. I asked him to repeat himself and he said, "I'll just swim over here." Um, okay. So my friend and I started chatting about nothing in particular, and Mr. Swimcap started awkwardly butting into our conversation. 

He wasn't trying to add to it, he would just keep asking random questions that we couldn't even make out. We kind of brushed him off, but then he started swimming around the pool, "accidentally" swimming into us. We moved to another part of the pool and tried to act like nothing was happening. This was a huge mistake.

He stopped trying to swim into us and just started just staring at us. Then, he said something like: "Hoowanblah-ate?" The conversation proceeded as follows.

Me: "What?"

Him: "Hoowannaoate?"

Me: "Dude, I can't understand what you're trying to say."


Me: "...Are you talking to me, or her?" motions toward my non-pregnant friend


Me: "Um... I'm very flattered, but no thank you."


Me: "Yeah. I don't want to go on a date with you."


Me: "Yes. I have a man. And we're fixing to have a baby."


Me.: "Yes, we do."


Me: "Dude. No. I don't want to go on a date with you."


Me: "Would I what?"


Me: "No! I'm done talking to you now. Please leave us alone." I went back to my friend and we started discussing exit strategies while the guy continued to talk to himself.

Luckily, my friend's male neighbor decided to hang out with us for a bit. Mr. Swimcap started ranting at the neighbor about who knows what, so we tried to enjoy the remainder of our time in the pool. A little while later, the security guard came by to lock up, and we all bolted out of there while Mr. Swimcap was gathering his things. 

The neighbor later walked me to my car to ensure there were no creepers lurking about.

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10. Fake It Till You Make It

When I was going to college, I was sitting in the cafeteria with a group of 11 people who all knew each other and were D&D nerds together. There were about four very attractive girls in this group. One of the guys was a kind of sweaty mouth-breather who had only recently "joined" our little group. He leaned over to one of the girls and started bragging about how he could do a perfect Zapp Brannigan impersonation from Futurama.

She asked to see, and he said, "If I said you had a beautiful body, would you take your pants off and dance around a little?" in Zapp's voice. We laughed in that awkward way. I then had to leave for class, so I don't know what happened after that. The next day, he got to the table before the girl he was hitting on did.

He struck a heroic pose and said "Kif, I have made it with a woman. Inform the men." The girl was mortified. Fortunately, he had the good sense to be too embarrassed to show his face again after that. But like…how did that even work??

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11. Cruel Intentions

I don't often go out, let alone to bars. I'm not a drinker, but I decided to humor my boredom and go out by myself one night. I put on a nice, floral spring dress and hit the town. I was at the bar sipping away at whatever I had bought when I spotted a cute guy sitting at a table and drinking with two other guys. He was laughing, having fun, and his smile was so attractive. 

Now, I am not the type to approach at all. I haven't even had a boyfriend out of school. I'm pretty quiet and shy so I tend to avoid those kinds of situations altogether. But this night, I had seemed to have bolstered all the courage that I had stored over the past 21 years of my single life. I decided I was going to buy that nice smiling guy a drink.

I’d read that a large percentage of guys liked this maneuver. I would simply ask the bartender if she knew what the guy was drinking and, if so, I'd ask her to make another for him and deliver it. I'd cover it, obviously. I thought it was perfect. It wasn't pushy, in his face flirting. If he wasn't interested, no big deal; he didn't have to approach me or engage in conversation.

I didn't think anything could go wrong. BIG MISTAKE. The bartender brought the drink over to the table. The guy seemed curious, and butterflies started flying in my stomach. He inquired about the drink and she motioned to me. I offered a friendly smile and a wave. They all laughed. And not a nice laugh, either.

Not a "Oh hey, you just got picked up by a chick, haha, that's it, bro, you got swagger" type of laugh. No, it was an "Oh my God, you got picked up by a beast; a pig magnet. Sucks to be you" type of laugh. One of his friends slapped him on the shoulder—and that's when he did it. He raised the drink I bought him in a toast, then dumped it out behind him into the potted plant.

And here is the part of the story where I wish I could say I stormed over there and slapped him. I wish I could say I tipped my own drink on him. Heck, I wish I could say Batman swooped out of a dark corner of the bar and punched him in the nuts. However, I cannot. I simply turned around immediately and left, feeling the most ashamed, humiliated, embarrassed, ugly, worthless, and downtrodden I ever had.

At least I made it out the door before the crying started. I haven't been to a bar since.

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12. Missed Connections

I was at Sears with my brother. I just wanted to buy a Perry the Platypus shirt. I went to the cashier and there was a cute girl at the register. She took my shirt. While she was scanning it, she asked for my number. I said, "Um, no thanks," because I thought she wanted it for marketing or to sign me up for a Sears card or something. She looked a bit disappointed.

She rang up the shirt, then I paid for it and left. It wasn't until a few months later that I realized that she wanted my number to call me and hook up. Darn.

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13. Follow The Motion Of The Ocean

I got a new job teaching computer courses to adults. I went to check out an apartment I found on Craigslist near my new job. The renter and I exchanged some emails. I told her about my job and she told me about the nutrition supplements she sold as part of her side business. She also told me a little too much about her life—her ex-husband, her custody battle over her 13-year-old son, etc.

Boundary issues. But I responded very sympathetically towards her because I'm a people pleaser with my own boundary issues. We hit it off! The address was a house, and I figured it must be a duplex of some sort. The renter invited me in—she was a 40-something woman, fairly attractive, and I was in my early 20s at the time. She introduced me to her son, who was in the living room playing Guitar Hero. 

Then she showed me the room—not even an apartment—which was just off the living room, separated by a curtain. I told her I was surprised—I thought she'd listed an apartment. No, she explained, it was just the room, but it comes furnished with the dresser and this waterbed. Don't worry about the curtain, she said. You'll have plenty of privacy; you just need to turn this fan on.

She turned the fan on. She sat on the bed and asked me if I liked waterbeds. I told her I'd never been on one. She invited me to sit on the bed with her, promising me that it'd be fun. I don't get hit on much. I'm a good-looking guy but I'm also quiet, and I'm just not used to having signals sent my way. But at this point, I put it together that she was inviting me to engage in shenanigans...

...While her son was 15 feet away. On the other side of a curtain. I got out of there as quickly as I possibly could and told her I had to think the room situation over. But that wasn’t even the end of the story. Epilogue: The next week, guess who showed up at my Level I Windows Vista-class? And guess who pretended he'd never seen her before in his life? This guy.

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14. Twenty Questions

I was walking down the street in the middle of December, hands stuffed in my pea coat and walking behind a young man who looked pretty paranoid. At some point, he finally stopped and asked:

"Do... Do you have any gum?” I pulled my hands out of my pocket and shrugged. No, no gum. "Oh. Do you have a lighter?" "Nope dude, sorry." "Oh. Do you have a boyfriend?" Priorities man, priorities.

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15. Guilty Conscience 

I was riding my bike and I got hit by a car. The guy stopped and we exchanged information. I got a call later and it was him asking me if I was alright, which I thought was nice of him…but then he followed it up by asking if I would get lunch with him. He then proceeded to call me every day, leaving messages like, "Wanna get lunch? I'm realllllly huuuuungrry."

You don't break a person’s tailbone and then ask them out.

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16. Rolling The Dice

I walked into a movie theatre and there was this gorgeous, tall, amazing brown-eyed guy. He said to me, "Excuse me miss, do you believe in love at first sight?" I looked up and smiled. This guy was so hot. It blew my mind that he was talking to me. This was a first for me. It was obvious his buddies put him up to it. So I decided that two could play this flirting game.

I smiled and said, "Why yes, yes I do," then I walked off. As I was opening the door into the theatre, I had this urge to continue, so I turned around and said he could sit next to me if he wanted. He was still standing there with a shocked look on his face. He probably thought he would get smacked for being that forward. I turned to go into the theatre and all I could hear were pounding footsteps behind me. 

We sat together. He ditched his friends to watch my movie with me. Five minutes later, he asked me to run away with him to Vegas and get married. Five months later, we did. We have been happily married for 22 years. BEST PICK-UP LINE EVER!!!!

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17. More Than He Can Chew

One time, my friend and I were at a bar. We were just sitting around, waiting for a girl to walk by. When one did walk by, we'd say “Hi.” If they stopped, we'd say, "Hi, do you know where my mom went?" in a child's voice. One girl came over, straddled my leg, and said, "Aww, are you lost?" I seized up and I don't remember anything else.

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18. Can’t Fake Chemistry 

Near closing time at a bar downtown, a guy saw me and decided to open with, "What's your husband think of that?"  It was nearly 2 in the morning and I was getting tired, so all I said was, "What?" He responded with, "Boyfriend?" I said, "I don't have a boyfriend." The gentleman, who was clearly worse off than I was, then said wistfully, "I wish this was real."

I left at that moment because I had to get a round of water for my friends, but I wish I'd stayed and continued the conversation. We clearly had some chemistry.

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19. If The Shoe Fits

I was waiting for the last train from Paris to go back to my good old suburbs. This was right after midnight—the station is quite empty, and only a few people were left around. I should probably mention that I'm a girl, and I was traveling alone. Anyway, I had about 15 minutes left to wait, and this old guy just sat next to me. 

After a few minutes, he got the courage to speak. “Could I ask you a favor,” he asked. I replied, “Sure?” “Oh, no never mind, it's OK.” He then looked really sad and miserable about something, so I tried and be nice, thinking he just wanted to talk about something. Nope. “Could I…see your feet?” Um, excuse me?!

“I think you have beautiful feet...could I just see them? I won't touch or anything, I just want to look! You can keep your socks on if you want.” At that point, I was quite weirded out. I was wearing Converse, and this guy was making me feel bad for telling him I didn't want to show him my feet. He kept insisting with this miserable look on his face.

He even suggested getting on the next train with him and if there were too many people on the tram, I didn't have to show him if I was shy or something. I actually felt like I had to apologize to him because I didn't want to show him my feet.

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20. Lady In Black

I was walking down a street in Berkeley that was often lined with older homeless guys and panhandlers. It was a warm day so I was wearing a cute but modest black-and-white polka dot-style dress that always got me a lot of attention from the men. Anyway, as I was walking, there were two older guys sitting on the sidewalk near each other.

They were far away enough to not encroach on each other's turfs. Suddenly, the first one I passed hollered something to the effect of "Hey girl, let me see that dress on my bedroom floor!" (Ironic because, you know...) To which the second homeless guy responded, without missing a beat, "Hey, don't you talk to my wife that way; she's a lady.”

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21. Father Of The Year

I was hanging out with a friend the day before Easter. She had to drop by another friend’s house for a quick errand, so I went with her. They had an Easter party going on for this woman's children and a few of their friends. The parents were having a BBQ and the kids had just done an Easter egg hunt. They were moving on to painting pictures for their parents. 

A normal fellow started chatting with me, and after about 10 minutes with the group, I realized he was there with his two-year-old and the baby's mother. I wasn't sure if they were together but I just assumed they were and left it at that. So when we went to leave, I was totally taken aback when he pulled me from the doorway where everyone was saying goodbye to each other. 

He shook my hand and whispered, “Shhhhh...It was so great to meet you. Shhhhh.” He put his finger to his lips, winked, and then turned me back around to face the group. I just stumbled through my normal goodbyes and left without acknowledging him. While walking away, I unfolded what he'd slipped me while shaking my hand. That note made my blood run cold.

It was his number and a note that said: “UR cute. Txt me”...torn from a large chunk of the Easter painting his child had proudly handed him 10 minutes before.

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22. Setting Up Camp

I attended a family camping trip in the summer, and we pitched our tents next to a small lazy river. On one of the days, I was wading around in the clear water, enjoying the sun. There was a group of men at the site next to us and a few of them were in the water downstream. A little later, one of them came over and started politely chatting with me. 

He said he'd “lost his class ring” and I believed him, so I helped him look for it. After he started mentioning how attractive I was, I noticed he wasn't looking very hard for his “lost ring.” He thanked me for trying to help him and then asked me if I'd like to come over to their site that night to drink and play poker with them. 

I awkwardly said no. Later, I had a bit of an identity crisis with my 16-year-old self.

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23. Home Alone

I was 17 and in charge of supervising the installation of carpeting in our new apartment, alone. My mom was at home, packing. This should have been an easy task. All I had to do was wander in every couple of hours to see how it was going, and the rest of the time I could go for a walk or hang out outside. The installers were two guys, maybe in their 30s.

They seemed nice enough, to begin with. I introduced myself and explained I'd be around in the building if they needed me. It became rather apparent that one of the two guys was being a little too nice, but I just shrugged it off. I was used to it because I looked older than I was and got hit on by older guys on occasion.

The problem was that he didn't stop, and there was a major storm so I was stuck in the building. Every time I was around, he tried to make small talk. He'd ask things about me and what I liked, and talk about himself a bit. He tried to flatter me and started acting rather "flirty." I tried to be polite, but also make it clear that I wasn't interested. 

Eventually, he started asking me out on dates and offered me his number. I kept declining, but he didn't stop. To tried casually work my age into a conversation. His reply made my blood run cold. To my dismay, his response was to flirt with me more and tell me that I could always call him when I turned 18.

His partner looked thoroughly embarrassed and kept trying to avoid eye contact. It was incredibly awkward and I didn't feel very comfortable because he refused to take no as an answer. At one point, I got stuck in the dang elevator with him and he "accidentally" hit the wrong buttons.

He then hinted at how nice it was being stuck with me alone. Gave me the total creeps. The day ended with him giving me the company card in case there were any problems, then winking at me and telling me to call him soon. His cell number was on the back. In hindsight, I should have complained to the company itself, because it really, really disturbed me. I wish I had.

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24. Let’s Not Get Ahead Of Ourselves

My stepsister and I were on a bus headed back to her place after a night out on the town. It was around 2 o'clock in the morning. There were a couple of 20-something-year-old guys sitting across from us. 

Guy #1: “Hey girls. Did it hurt? You know, when you fell from Heaven?”

Me: “Yeah. A lot. It's a pretty long fall.”

Guy #1: “Where are you girls from, anyway?”

Stepsister: “Umm, here?”

Guy #1: “More like from Beautiful Town. Because you're beautiful. Or…wait…no…more like the Gorgeous City...because you're so gorgeous.

Guy #2: “Erm...” 

Guy #1: “Hey. HEY! Want to go on a date?”

Me: “Sorry, I have a boyfriend and he probably wouldn't like that very much.”

Guy #1: “I'll take you on a date your boyfriend would never take you on!”

Me: (laughing) “Oh yeah? Where wouldn't my boyfriend take me?”

Guy #1: “I'd take you for dinner at the top of the revolving restaurant.

Me: “Oh yeah?”

Guy #1: “Yeah. Then we'd break the window and jump out,” After that, there were total crickets. 


25. A Rite Of Passage

I was at a beach with three other friends. It was a weekday, so there wasn't a crowd, but a bearable amount of people to handle. We were enjoying ourselves, and my friend and I were just floating about, talking. Then I noticed this tanned guy not too far away from us. He was staring straight at us with an extremely creepy and perverted grin.

We decided to swim back to shore and take pictures. Guess who decided to come along? Creepy tanned guy. At this point, we still really hadn't reacted, but then he started RUNNING back and forth on the beach, never taking his eyes away from me and my group. He eventually started doing his little running routine, closer and closer to us. 

When we thought it couldn't get weirder than that, it did. Every time he ran towards us, he slowed down, eyed us up and down, and then smiled his creepy smile. Then, at some point, he began CHANTING. He was chanting actual gibberish—no English words or any language you'd recognize. It was like he was performing a ritual on us. It was creepy as heck.

26. Some Guys Have All The Luck

I was walking through a mall in my area wearing a top hat, some classy glasses, a bowtie, a fake handlebar mustache, and...well, a batman cape. No fewer than three girls ended up giving me their phone numbers, and I have been in a relationship with one of them for about five months now. Honestly, I’ve never understood that…

27. I Tried, I Failed

I was with my friends at a Steak N' Shake at 3 or 4 am one night. The waitress decided I didn't have to pay for my meal, so all I got was a piece of paper with her phone number on it. I'm the most awkward person that has ever lived, but I gathered my courage and went to talk to her. Two minutes later, she took the phone number from my hands and said, "Have a nice night!"

28. A Golden Opportunity 

I was attending a party while in college. I was just trying to hang out and be in the scene. My fiancée was out-of-state, so I had no desire for female companionship. A girl stumbled over, wanting something to drink. We chatted a bit and I realized that she was looking to hook up with me. Being the gentleman that I am, I pondered on how best to approach this sticky situation.

How to rebuff this girl without possibly upsetting her? While pondering, I realized that I needed to got to the bathroom. I stood up to go off of the front porch of the house; something that I had been doing every 40 minutes or so. While doing my business and gazing thoughtfully out at the cars driving by below me, I was presented with the perfect opportunity. 

As luck would have it, instead of continuing my earlier system of peeing between the slats in the low fence surrounding the deck, I was peeing directly onto this vertical support, soaking the front of my pants with copious amounts of liquid. In other words, I didn’t think that girl would want to get it on with me at all after that, thank goodness. 

29. Order Up

I was in line at Starbucks. There was only one person in front of me and he was placing his order. He finished ordering his drink and then said, "So now what?" The barista behind the counter said, "Now this is the part where you give me money." He calmly asked her, "When is the part where you give me your phone number?" 

She responded with, "Well, this is the part where I introduce you to my husband, he's standing behind you." He looked over his shoulder and sheepishly said hi to me. I said, "It happens to the best of us." He stared at the ground the entire time waiting for his drink. Yes, my wife was wearing her engagement ring and wedding band.

30. Love Is A Religious Experience

I'm a hospital chaplain, and being with people in some of their most vulnerable moments can lead to some pretty ridiculous encounters. Last year, I was sitting with a family at the bedside of a rapidly deteriorating older woman. I had been speaking with the woman's spouse when his son walked in, sat down, and looked me straight in the eyes.

He said, "Is my dad flirting with you? I bet he was flirting with you. I have to say, you're a very attractive woman and if it were me, I know that I would be flirting with you." First off, I'm the chaplain. Second, the man's step-mother was dying. Third, he accused his FATHER, the spouse of said woman, of flirting with me. 

At his passing wife's bedside. He went on several minutes later to tell me about his new bride who was still living in China and waiting to move to America. I wish I was making this all up. I would feel better about humanity if I were.

31. Keep It Professional 

There was this guy I used to work with. Let's call him Marcus. He tried pretty hard to get with me in a variety of ways. He would accuse my boyfriend of being controlling by saying, "What? He doesn't let you have candlelit dinners with friends? He doesn't trust you?” When I would ask him to stop flirting with me, that only made things worse.

"What? Do you think I'm hitting on you? God. Why do you think that? I'm just trying to be friends with you and here you go reading into the situation." I ended up talking to a few supervisors about how uncomfortable he was making me because he often cornered me while I was at my desk. 

32. Try, Try Again

Many years ago, my friend was in a gay club. He used the facilities, and as he was leaving, he found the door blocked by a large, built man. My friend is 5"9 and he swears this guy was a foot taller than him. So here was my friend, staring up at this massively built guy who was blocking his exit. He started thinking, “Oh my God, this is how I go." 

Then the guy rumbled out a question: "Hey man, you want to come home with me tonight?" My friend did the only reasonable thing and burst out laughing. He ended up having a drink with him and being the guy’s wingman for another chat-up attempt that was successful.

33. Wrong Place, Wrong Time

I had just gotten out of the hospital a few days earlier. It was my first real surgery and it was a doozy—I'd had my entire large intestine removed. I had been recovering fairly well, but around noon my gut started hurting. A few hours later, the pain had progressed from "light rug-burn" all the way through "shattered hand" to "giving birth through my belly button." 

That was when we called the surgeon. It didn't sound too serious to him, but he told me I should probably come into the hospital just in case. He used some fancy words like "food bolus," "peristalsis," and "postoperative ileus." About then, I started vomiting from dehydration. Turns out, when your gut stops, regardless of the reason, you don't absorb liquids very well. 

Add to it a couple of fresh, long abdominal scars and a distended gut, and an hour-long car ride to the ER. It already didn't look like it would be a good night, but it was worse than I could have ever imagined. I arrived at the Emergency room. The place was as busy as a hungry badger in a woodpecker factory. By this time, I'd started vomiting actual poop.

I grabbed a small trash can on my way out the door, so it was relatively contained. My hands and feet started tingling. I was told to wait as they would admit me as soon as they could find a spot for me. The pain was getting worse, and I started to wonder whether or not I'd pass out before I got treated. That’s when some random girl sat next to me and tried to strike up a conversation. 

She batted her eyelashes at me a few times. I threw up again and got up to clean out my trash can. I sat back down somewhere else.

34. A “D” For Effort

I was 22 and at a bar with some friends. I just got out of a six-year relationship, so I wasn't really looking. I was just enjoying being single for once. I was there for about five minutes when a girl walked up, said hi, introduced herself, and...that was it. She just stood there, radiating this body language that said, "Yeah, I've presented myself, now make your case." 

I found that totally unattractive and proceeded to keep on following the conversation of my friends. She did not like this. She asked how old I was and when I told her, she told me I was too young. Then, she asked me what I was drinking and suggested that I buy her a drink. I did not, and so she left to find her friends. An hour went by and it was getting pretty late. 

As we were about to leave, I felt a poke from behind. It was her. She said it was getting really late and that she could use a ride home. "Your place is probably closer," she added. I couldn't help it at this point—I chuckled, then I wished her good luck getting home. Ain't that hard to flirt, folks. Just don't be like that girl.

35. Quick On His Feet

I was working the concessions counter at the movie theater and this guy started chatting me up. I was not interested in him for a myriad of reasons. He said, "What are you doing after work?" I said, "Going right home and to bed." Without missing a BEAT, this guy said, "Well, mind if I join?" I still said no, but I had to give him props.

36. Double Dipping

I gave a speech for a class once. Afterward, I went to the bathroom and got a drink. On the way back to class, a cute girl from the class was in the hall, looking like she was waiting for someone. I assumed she was waiting for her boyfriend since he was also in the class with us. She saw me and lit up, asking if I wanted to keep her company. 

We headed outside. We joked around a bit and she tried flirting with me, but I had a girlfriend and I didn't reciprocate. I figured she was just a bubbly person. Right when we were about to head back, she handed me a slip of paper with her number and said, "You should give me a call later today...then we can get to know each other better."

I asked her about her boyfriend and she said, "He's working later." I, of course, politely declined, went back to class, and spent the rest of the day wondering why these scenarios always happen when I am in a happy, committed relationship. When we got back to class, she gave her boyfriend a peck on the cheek and sat back down next to him.

37. A Trip Down Memory Lane

When I was 21, I went to sing karaoke at a bar in my hometown. I don't visit often, and one of my uncle's friends thought, "Girl, I remember when you were four years old" would do the job. It did not.

38. The Desired Effect

The first time I asked a girl out, I put on a fake mustache, walked up to her, and said: “Hullo, my name is Awkward Turtle, and I find you attractive.” She walked away very briskly.

39. Long Hair, Do Care

I’m a guy. At some point in the distant past, I used to have really long hair. I was into metal and generally had an angsty attitude. Women would frequently compliment my hair because it was gorgeous—long rolling curls, naturally flowing, and super easy to care for. 

Anyway, I was walking down the street minding my own business when I heard the familiar sound of a redneck truck slowing coming up behind me, presumably to give the passenger enough time to crank down the window..."Hey baby! Yer lookin' real purdy!” I turned around. As the creepy, snaggletoothed grin faded from his face, his eyes narrowed as if to see me more clearly. 

Anger replaced his previous lust, and he unleashed a veritable cornucopia of invectives. I could hear his buddy guffawing as they attempted to speed away.

40. Take The Hint

About two years ago, I was working as a bouncer at a fairly popular bar in my hometown. If any of you have worked as a bouncer, then you know how often random girls come around and hit on you. Needless to say, I was loving life the entire time I worked there. So one night, one of my regulars came in with her 19-year-old sister in tow. 

She'd been 19 for a week and it was her first night at a bar. She was clearly nervous about it, so I assuaged her fears by just off-handedly mentioning that I'd make sure nobody messes with her. For the rest of the night, she rarely let me out of her sight. She consistently tried to strike up a conversation until I politely told her that I was working.

Still, she hung around in my general area. When the night ended, she gave me her number. Being polite (but not interested), I took it and never called her. The next day, I went to my day job as the assistant manager of a book store, and guess who walked in? I didn't think much of it at first, so I was still friendly with her.

I helped her find a book and she went on her merry way, asking me to give her a call. That night, I worked at the bar again, and she was there again; this time, without her sister. She proceeded to drink and sloppily followed me around to the point where I had to call her sister and have her come to pick her up. The next day, I was back at the bookstore, and who should show up? Yes. Her. Again. 

She was now following me through the aisles, trying to talk to me while I was working. I very blatantly told her that she couldn't be bothering me while I was working. Anyway, eventually she got my number through a mutual friend and she called me within 10 minutes of my shift ending, asking if I wanted to hang out. At this point, I was getting mildly annoyed, and I straight-up told her that if I wanted to hang out, I would call her.

Silence for a couple of days. I thought I was finally safe...but I was so, so wrong. She then starts texting me like a madwoman, basically spilling her heart out and telling me she was in love with me. It had now gotten to the point where I was literally creeped out. This girl would just not take the hint. So I blatantly and outright told her that it was NOT going to happen.

I firmly told her that I was NOT interested. She quickly retracted and apologized, but also said she still wanted to be friends. Having been down that road before and knowing that it would only give her a glimmer of hope that it MIGHT happen, I told her straight up: No. The next day, I get a horrific text from her. It said she tried to off herself and that she was in the hospital.

Thinking it was just another cry for attention, I didn't even respond to the text. A day or two later, her sister came back to the bar and I chatted with her for a bit. As it turns out, she wasn't lying. She really tried to. The weirdest part of it all was that I ended up hooking up with the sister a few nights later. She was far less crazy.

41. By Any Other Name

Back in the days when the whole Twilight fad had just started, my mother had bought me a "Team Jacob" shirt. It was stupid, but she bought it a size too big so it ended up being extremely comfortable. I wore it on a long ride out of town—no one was going to see it since I was in a car, right? But then we stopped at a gas station and I went inside to go to the restroom.

On my way out, I saw an older man (a truck driver, by the looks of him) with his eyes on me. As I walked by, he hollered: "My name is Jacob!" and then he whistled. Needless to say, I rushed back to the mom-mobile and hid in the back. I had never been hit on before that point, and as long as I live, my mother will never fail to bring up that story to friends and family. 

I've even had a few family friends come up to me and say the same thing...no stupid shirt needed.

42. A Whole New World

I have one where I was accidentally the creeper. I don't remember it but I was told later what had happened. I was having my wisdom teeth removed and I was just coming out from the influences of the gas. Apparently, I had taken a fancy to one of the assistants, and in my laughing gas stupor, I thought that immediately post-surgery would be the PERFECT time to make a move. 

It still makes me cringe to this day, thinking about this poor girl seeing me, caked in dried blood and drool, in front of all the other doctors and hygienists, sloppily telling her that I thought her hair was pretty. I told her to call me some time because (apparently) I had a magic carpet.

43. Love At First Sight

One of my friends is very much a lesbian. She was at a Panda Express by herself a few days after moving back to her old city. Some dude came up to her and said, "Hi, I think you're very pretty," which she was...in a girl-next-door kind of way. He extended his hand. She shook it, then said something along the lines of, "Hi, but just FYI, I'm gay." 

They then proceeded to go back and forth with him going, "Really?" and her replying "Yeah," I'm assuming with increasing amounts of annoyance on her part. THEN THE GUY SAID: "WE'LL SEE ABOUT THAT." HE GRABS THE BACK OF HER HEAD AND WENT IN FOR A KISS. Like, what the heck did he expect to happen, besides getting punched in the face?

Well, that’s what my friend wishes she had done in hindsight. And no, she did not let him kiss her. Thank God...

44. Words Are Hard

One day, a group of us were all out, and my friend said he had a great pick-up line. It was: "Are you my toe? Because I wanna bang you against furniture at my place." My other friend, already a few drinks deep, insisted that he would try it on a hot girl at the bar. We followed him as he approached and said: "Hey are you my toe?... Cause...you look...like my toe..." He did not get the girl. 

45. On Spec

This guy came up to me randomly in a bar and said, "Those glasses make you look like a model.” When I visibly put on a “what the heck” look, he then panicked and said, "No no, I meant they'd make me look like a model.” He then plucked the glasses off my face and put them on like, “See??” I did not see, because funnily enough, I couldn't see without my glasses.

46. Simple As Pie

I was at a concert and I overheard a girl ask a guy, "Hey, can I borrow your lighter?" "Sure, here you go. Can I borrow your number?" "Sure, here you go." That actually worked?!

47. Blast From The Past

I was working at a restaurant in my hometown. A guy walked by and gave me the double-take. He came back a few minutes later to talk to me, But I knew something he didn’t know. I had recognized him right away—I had a serious crush on him back in middle school. He was a few grades above me, so of course, he never spoke to me. I was also quite the ugly duckling.

As he started to flirt with me, I realized that he didn't recognize me at all, and it made me laugh. I had to explain why I was laughing, and he got kind of embarrassed. He left me his number and walked by the restaurant a few more times to smile at me. It made me realize how far I'd come, and was a huge ego boost, to be honest. 

48. Friends In High Places

I was detained in high school for a spontaneous bout of stupidity. As I got into the officer’s car, I realized that there was a teenager doing a ride-along with the officer. I didn't think much of it since I was, you know, pretty busy focusing on how much trouble I was going to be in. A few days later, as I settled into my permanent grounding, I got onto Facebook. 

Lo and behold, I had a Facebook message. The boy doing the ride-along had written down my contact information and found me on Facebook just so that he could send me a message...

"Hey Girl, I just wanted you to know that I hated arresting a woman as beautiful as you."

49. In Over His Head

I’m a lifeguard and have been for many years now. In my first year as a lifeguard, I was 15 years old and working at an inner-city pool in my community. It was really poorly run and had no real rules, so as lifeguards, we could wear what we wanted. I treated it as an opportunity to tan and I wore my bikini regularly. I was also pretty developed, having a C cup at that age.

Well, I was just sitting around and this 40-something hairy guy was under my chair, staring at me. I tried to brush it off, but he just kept staring at me. I was like, can I help you with something? He started to comment on my body, even after I told him I was 15. I only got him to get the heck away by threatening to call the authorities on him. I wish that was the end of the story. 

Two hours later, I was guarding the deep end and this jerk jumped in and pretended to be drowning. I stared at him for a minute, but as the only guard, what else could I do? I threw my tube to him, but of course, he played around and went to the bottom. I was so, so angry. I got an officer to come over, and luckily my older brother was also a guard so he pulled him out of the pool. 

He was kicked out for the rest of the summer.

50. Red, White, And Blue

This is one that worked. On the Fourth of July a few days ago, my friends and I spent the afternoon at the pool of a local college apartment, wearing tacky patriotic shirts from K-Mart. I went full-out, with American flag swim trunks and a tie-dye red, white, and blue shirt with a bald eagle print. It was a great time; we pulled some deck chairs into the shallow end and sat there, drinking and lauding our nation's fine achievements. 

The only problem was, there were three little kids with water guns spraying strangers. Real parents of the year, bringing kids to a college pool party. I struck up a conversation with a cute girl in a nearby deck chair about how obnoxious and terrible the kids were, and we ended up talking for an hour or two, hitting things off really well. 

My friends were ready to leave, so we put our shirts on and packed up the remaining drinks. I said, "Guys, wait." I jumped into the pool, wrestled the water gun from one of the little kids, and sprayed him right in the face. People started cheering, and he may have started crying—who knows, his face was already soaked. I walked out and passed the girl from earlier.

She said, "That was really funny, but you got your shirt wet." I immediately respond, "Don't worry. These colors don't run." I walked away without saying anything else. As I was getting into the car, she came running out and said, "Don't you want my number?" 

Sources: Reddit,


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