Real Life Crushes That Turned Out to Be Totally Cringeworthy

Real Life Crushes That Turned Out to Be Totally Cringeworthy


The course of true love never did run smooth, and we've all experienced a few heartbreaks along the way. Some romances, though, are more embarrassing than others. Here are some true life stories of cringeworthy crushes that are better left in the past.

Fight or Flight


In the 7th grade I was a very awkward child. Kinda chubby, no fashion sense, and my face generally resembled a gorilla. I had already accepted the fact that boys weren't going to like me.

One day I was hanging out with a guy friend, Richard. Richard was a sweet kid and pretty cute and I'd met him through another friend. It was just Richard and me chilling in a hallway when he suddenly asked me to the school dance that was happening on Friday.

I couldn't believe it. A cute guy had just asked me to a dance?! Are you sure this is real life? Say yes, you idiot, say yes!

So of course I did what any reasonable 13 year old girl would do; I screamed and ran away. Richard didn't want to hang out with me again after that and I still feel bad about to this day, a decade later. Story credit: Reddit / red_raconteur

Not the Worst Thing To Find in Someone's Search History


Went to a guy's house to do a project in high school. It involved the Internet and while he sat next to me I tried to navigate to Google.

Unfortunately, the address bar auto-filled and took me to his last Google search… page two of results for my name. Every link had been clicked. We both just sat in silence. Story credit: Reddit / [deleted]

Skin Art


During camp once i overheard of a girl who was into me. I wasn't that much of a fan of her so I didnt follow it up The day after, I come past this girl and notice part of my name written on her hand.. Asked what the deal was.. she lifted her sleeve and my name was written all over her body.

I WAS SO FREAKED OUT didnt know how to react, I just ran away.. I bump into her here and there nowadays.. Its still extremely awkward...(shivers) Story credit: Reddit / asherwiener

Secret Admirer


In high school, this guy who liked me used to leave love notes in my locker. They always had really disturbing pictures or poems in them. Not knowing that it was a friend, I used to bring them to the morning table to be like, "who is leaving these in my locker?!?"

I feel bad about it now because it seems everyone knew it was him, but me. Story credit: Reddit / dedicatedreject




A girl walked up to me and said, "You're my boyfriend now. Accept it, or I'm breaking up with you." Story credit: Reddit / ElectricBlaze



When I was in the 4th grade I remember having the biggest crush on a girl in my PE class. Having thought things through, I decided that I needed her to know my undying love for her. So I wrote her a note to deliver to her in PE.

So finally when we're all sitting in our grid formation on the gym floor I decide the time has come. I get up and start walking to the fountain (she is in between and I planned on just dropping her the note en route).

However, in the 5 seconds between me getting up and when I am to drop the note off I decide that this is too easy - I must give her a challenge.

I then proceed to the water fountain with a new plan. As soon as I get there I plunge the note into the water creating a wet squishy mess that resembles a white lump of goo.

My logic at this point in my life was that the wet paper would create a situation in which she would have to spend some time decoding the note. By making the note harder to read, she would undoubtedly be impressed.

On the way back to my seat, I dropped the white piece of crap off with her. As you can probably guess, she didn't know what in gods name it was. She just stared at it on the gym floor for a second with her mouth open. Before she could say anything I high tailed it back to my seat.

She not once ever spoke to me again. I think it is safe to assume that she did not decode the message. Story credit: Reddit / ghrey_ink

Going Public


I once sent a girl an email, in reply to a mass email from a university course we were taking together, professing my interest in her...

I clicked "reply" not "reply all" so I thought I was safe. I didn't know how "list serves" work. Story credit: Reddit / Trubbles

Plan B


Close friend tells me she has had very strong feelings for me for the past three years. She tells me this a couple days before we graduate college (I didn't feel the same way about her).

According to a mutual friend, her original plan was to romantically profess her love on the day of our graduation in front of all of our family and friends. Story credit: Reddit / solinvictus7

Radio Replay


A couple of years ago I worked the counter at a Chinese restaurant. They were a fairly busy place right beside my house and I would work for a few hours almost everyday after school to get them through the rush.

As a result I had a lot of regulars who I recognized and I behaved in a very friendly, familiar way with many customers. One guy would come in around 9pm once every couple of weeks and was very quiet.

I would give him his food and he would stammer out a thank you and make terrified, jutting-all-over-the-place eye contact during our interaction. This was no problem. He seemed like a normal middle aged man.

One night he picked up his takeout bag and somehow managed to get his finger snagged under a staple and cut himself. He started bleeding pretty profusely and I grabbed some napkins, trying to help him but he kept playing it off and just booked it out of there.

The next day I get to work and a bunch of my customers are telling me they heard about me on the radio. Apparently, this guy was a very popular morning radio DJ and he had been talking about a girl he gets take-out from and is completely in love with for months.

He would mock all of his awkward interactions with me and profess his love and how beautiful he thought I was and I guess that in telling the most recent staple story he revealed that I worked at a Chinese takeout place and a ton of my customers/coworkers put it together.

Everyone was recounting all of these cringey, humiliating things that the guy had done while picking up food from me that I'd barely noticed or remembered. It was so weird. I felt like a tabloid celebrity.

He kept coming in and I never told him that I knew he made a habit of mentioning me on the air but I did try really hard to make sure our interactions went smoothly and to bolster his social confidence a little. Story credit: Reddit / AshleyBanksHitSingle

Instant Commitment


So I met this girl at a bar. Nice girl, cute blonde, typical college type, I exchanged numbers with her thinking we could hang out again. Fast forward to a few days later, when we were just texting back and forth setting up a date:

Her: How's tonight sound for you? Me: Ahh I can't, I'm meeting my friend for drinks because she's leaving town.

Her: Wait, you didn't tell me you were seeing other girls. I thought we had something going on. I'm sorry I can't do this, please stop texting me. I just told her I'm meeting a good friend whom I've known for years and she refuses to listen.

So I thought, great, I dodged a real crazy bullet right there. Then she texts me saying she wants to meet again, and I said no, because she was being a little crazy and making me uncomfortable. Here are some of the best (creepy) texts that she sent next:

No, I won't stop texting you until you explain to me why you won't come out and see me. (I already told her she was being overreactive and making me uncomfortable and I lost interest.)

Do us a favor and stop being a jerk. Why can't you put the past behind and give us a second chance? Forgiveness is a virtue.

Just pretend that never happened and we can be happy together. I'll give you a day to get over it. We don't have to meet immediately. We can text and see how we feel, I am in no rush.

I'm so glad iOS7 has a built-in block feature now. I'm still keeping the texts in case something happens to me in future. Story credit: Reddit / crustation


Meeting the Parents


Freshman year of High School, a girl had a thing for me. She would talk to me in the halls a lot, and stare. Well, one day, as I was getting picked up by my mom, she flung herself onto the hood of my car and professed her love for me.

In front of my mom. Mom hasnt let me live it down yet. In fact, its a topic of conversation when we have guests over. Story credit: Reddit / [deleted]

Feed Her Poetry


I once wrote a love poem about the girl I liked. Apparently, "The complexities of the human brain, unravelled by your long blonde mane" is not a line that attracts women. I don't know if I'm more embarrassed by the rejection or the awful poetry.

So love is nothing...

Love, excrutiatingly painful, why do you steal my heart?
I try to ignore you, but you're always there,
Gnawing away, driving my mind insane,
Filling my body with your delusional dreams, ignoring the obvious truth.

I don’t know why, it just is so, you cloud the brain with doubt.
Love, lust, I do not know you, why do you persist
In this game of yours?
What did I do to deserve this, why must you be so
Cruel that you do not love me yourself.
You took my love but nothing in return, just the void…

A black hole sucks you away from me, fate
Why Be So?
The complexities of the human brain, unravelled by
Your long blonde mane.

Oh one kiss one kiss one kiss I cry….
But nothing in return.
Darkness closes on this dwindling light,
One day it will shine bright

Story credit: Reddit / Schwenkfelder



Met a girl in my chemistry class, we started talking and usually sat next to each other. One day I mention that I'm a little hungry and will probably get lunch after class.

She says she's hungry too and we decide to get lunch together. Normally I'd be excited that a girl even talked to me, but she was way out of my league, so I didn't think she'd even have a morsel of interest in me.

After lunch we go back to our Residence Hall, we lived in the same building. I go to get on the elevator to go up to the 6th floor, and she stops me by placing a hand on my forearm and says "wait, I think I left my sweater in your room" I simply look at her and say "you've never been in my room before"

After this I facepalmed so hard, and I regret it everyday. Now she doesn't even look at me. Story credit: Reddit / pantsofcake



I was 10 or 11 years old and had just gotten a Gameboy and Pokémon red for Christmas. A boy in my class noticed and was superexcited. He watched me play and eventually got Pokémon blue for himself so we could play together.

We bonded a lot over Pokémon and played at every lunch break. Of course I didn't get at the time that he had a crush on me as he was a very shy kid and I was new to this thing of boys liking me.

Eventually we started going home to our own places and play after school. At this time he'd started to warm up to me so he decided it was a good idea to start farting really loudly. I still remember us sitting in one sofa each in my living room and him letting them rip every other minute.

He declared happily how great it was to be home from school because he could fart, and I just sat there wondering what the heck had just happened. Story credit: Reddit / dubbelbasse

Eating Windshield


In high school I have a very diverse group of friends, and usually bounced around in the lunch room. I got to hanging out at a certain table to spend time with a specific girl. For the purposes of this story, her name is not important. At her table though was a guy named Sean.

Sean had a freshman that had a HUUUGE crush on him that lived halfway between our houses. Sean and I started hanging out a lot, and she would always see us going back and forth and get on her bike and try to ride past us and stalk Sean. One day at school Sean flips out on her, and I call him down.

I understand his frustration, but the way he did it was cruel. From then on, she decided I was her new object of affection. She would ride her bike around my neighborhood when she thought I was home, and always drove to Sean's when I went over there.

If I turned into my neighborhood, without fail she would hop on her bike and try to make it to my cul de sac before I got in the house so she could wave to me. Sean loved it. One day, I'm over Sean's house and she comes riding by on her beach cruiser.

After a couple passes, she sees us looking at her, smiling (making jokes at her expense), and so she misinterprets and waves emphatically... BLAM!

She runs headfirst into a parked car and messes her face up. She tries to play it off and smile, but she cut her lips up, knocked out a tooth and chipped one or two others... I put her in my car and drive her home, tears streaming down the blood running down her face...

Blubbering about how much she loves me and how stupid I probably thinks she is. We pull up at her house, and I tell her I don't think she's stupid at all. A look of pure benediction melts into place on her face, and she leans in to try to kiss me, bloody face and all.

I pull back disgusted, and she runs into her house crying and screaming incoherently. I look over, and Sean is on her bike near my car laughing, and he saw the whole exchange.

The girl's dad comes out of the house with a bat, obviously unaware of what transpired and merely reacting to his daughter being jacked up and babbling about the guy(s) outside.

Sean drops the bike and hops in my car, and we speed off. She told her parents we caused her to crash, but Sean's neighbor saw it all and called the cops when she 'left the scene' with me.

It took us some time to get people straight on what really happened bc the rumor mill ran far ahead of the truth, and the neighbor was the only reason we didn't get blamed for assaulting her.

People at school believed what they wanted to. But Sean and I knew what happened, and I still cringe every time I visualise her eating windshield... Story credit: Reddit / Th3DragonR3born



In Year 8, before the time of texting, a boy who liked me gave a girl on my bus a letter for me.

It was a letter confessing his love for me. Written entirely in 50 Cent lyrics.

The closing line being - "I luv ya like a fat kid luv cake, you no my style ill say anything to make ya smile ;)" Story credit: Reddit / 1squashedfrog462


Eye of the Beholder


Back in middle school, this one girl who had a crush on me kept staring at me during class. All the time. Every time I happened to look at her, she'd be smiling back at me.

Then she wrote me a love letter and I was like "Aww...". She was a really sweet girl but the staring honestly made me feel uncomfortable. Story credit: Reddit / Coveiro

A Bit Too Sweet


I've had a few cringe-ish crush moments, but a particularly bad one was a guy I used to work with who was seriously a stage five clinger. He wanted a hug every time we saw each other. Not just at the start of the day, but literally every time we passed each other.

He was a very sweet guy, but just too sweet for me - my bestie and I used to say he was the kind of guy that would want to stroke your face and look into your eyes lovingly when you slept with him.

His hugs started getting too romantic, and one day he caught me in a really bad mood (I had a virus, I shouldn't have even been at work) and I absolutely snapped at him. I felt bad, and we didn't speak for a week, but in the end we made up.

He is with a girl now who is as clingy as he is. They have a baby. Good for them. Story credit: Reddit / DextersLittleHelper

Yeah, Haha


First year of highschool. There's this girl I knew in Elementary, we were pretty good buds back then, but then we didn't see each other for 4 years. We didn't really talk much since highschool started, except for the usual hello-hello.

So one day, around the middle of the semester, she sees me as I am climbing the stairs, going to my classroom. She calls me, I turn around and she says something flirty (I can't remember what exactly, as I tried to erase this memory from my head).

I wasn't really interested in her romantically at the time, so I shrugged it off, said something along the lines of "yeah, haha". Then, out of nowhere, she says "CAN'T YOU SEE I LOVE YOU?", as if she had made it obvious all this time but I failed to notice.

I was too creeped out at this point, so the only thing I did was smile and continued up the stairs, without saying a word (or talking to her for a few months after that). I still cringe to this day. 15 yr old me was pretty stupid. Story credit: Reddit / lookingforusername

Woah, It Worked!


This was a few years ago. I had a huge crush on this chick who worked at Starbucks. But I didn't know her schedule or her car. So, a couple times, I would walk in and ask if she was working. If she wasn't, I would just turn around and walk out. Yeah.... I'm not a creepy weirdo at all.

The wedding was two years ago. Seriously. I'm still cringing at that move, and somehow that didn't scare her off... Story credit: Reddit / explosive_donut

Birthday Nope


High school, 14 years old, had a huge crush on this girl who was in a few of my classes.

One day I was leaving science class and someone behind me says my name. I turn around to see my crush and her friend. Her friend had spoken to me. She continues: "Hey did I tell you it was [crush]'s birthday today?".

I look at her, look at crush (who looks nervous) and I think 3 things: 1) I've never spoken to you before; of course you didn't tell me it's her birthday. 2) Hey it's my birthday in a few days! 3) Ohmigod! Crush is right there looking at me!

I quickly say "No.", turn on my heel and leave. Only realised a couple weeks later she was probably going to invite me to a party or something. Everyone I've told this story to confirms that suspicion. Story credit: Reddit / Kovhert

Third Time's The Charm


Told a girl I liked that I loved her before we even started dating, we were about to, but that sure put a stop to it. I didn't really love her, I just thought that was what couples did.

Sadly this wasn't the first time I made that mistake. However the 3rd girl I said "I love you" to I did at the right time and now we're married so I guess 3rd time's the charm. Story credit: Reddit / Iintendtooffend


Down on One Knee


Was walking with an ex through a park. Bent down on one knee to tie my shoelace and heard her gasp and say "yes". I looked up confused, then both of us looked at each other horrified when we realized what just happened… Story credit: Reddit / marcallanteart

Alive and Kicking


My best friend when I was small was my mother's best friend's son. He was 2 months older than me and we were together all the time for obvious reasons. I adored him in the little brother/best friend sort of way (he was always smaller than me).

We played together all the time and built forts in the woods, went fishing and swimming. We even ganged up on our younger brothers together. In second grade we had the same teacher and he asked me to go behind the bookshelf because he needed to talk to me. He crouched down so I crouched down.

He said, "Okay...will you be girlfriend? Phew! I finally did it." I smiled at him and said, "I can't be your girlfriend, I'm your best friend." He kicked me and walked away. Story credit: Reddit / Sugarbear51

Record Keeping


In grade 9 or 10, I found out a girl in my class had kept a daily log (over the past year and a half) of the colour shirt I wore. Also I found sheets and sheets of paper with my name printed all over it. Story credit: Reddit / ghostfan9

Happy Dance


I was head over heels, ridiculously in love with this amazing blonde. I'm in a store when I get a message from her, and as soon as I that she's the sender, I break out in my silly happy-dance and sing. Thrilled, I open the message. It says "I can seeee you :)".

I turn around, and of course she's right there, with a shocked smirk. Neither ever acknowledged it, but it still gives me the heebie-jeebies when I think about it. Story credit: Reddit / onanym

Frozen in Carbonite


When I was in highschool, I was in Spanish class with a girl who had a crush on me. I loved this class because I had it with a few friends and the teacher was cool and I made a lot of jokes - I was unpopular until my Junior year so this was all new to me.

So, one day, I went to class and was joking around and Spanishing it all up like I typically did. Then this girl who I had talked to but wasn't really friends with had a note passed to me. She sat across the room, so like a dozen people were involved in passing this note to me.

I opened the folded paper and read, "Are you going to see the new Star Wars movie?". I had seen the old ones but wasn't really interested in them that much (I've rewatched them since then and love them).

But at this point I didn't like the movies so I said, "No!", and gave her a look like she was stupid for even asking me such a ridiculous question. Everyone looked at her and apparently knew what was going on. She kinda slumped down in her chair and said, "nevermind," really sheepishly.

It wasn't until after college that I figured out that she was trying to ask me out on a date and I rejected her in front of the entire class. I feel horrible now. I totally would have gone with her, she was pretty cool. Ladies, you have to spoon feed us when you're interested! Story credit: Reddit / ChesterHiggenbothum

Maybe She's Worth It


It was my first year of college. I met a guy in one of my classes and we would write notes to each other mainly about how boring the prof was. I could tell he was interested, but the feeling wasn't mutual.

One day he wrote on my notebook, "Why are you so beautiful?" I wrote back, "Maybe it's Maybelline". Story credit: Reddit / rmaclaw79

Nope Out


My married housemate has a hankering for me (we live with his wife and child). Not my type at all and the fact that he wants to see how I'll react, then if it is bad he will work things out with his wife... is extremely off-putting. Found this out because he posted about it on reddit under a throwaway asking for advice.

He made it sound like married life was a horrid hell and I was the picture of perfection. I had no indication of his feelings before (though Im known to be dense about these things). Bonus points- his wife is kind of into my boyfriend. We both are nope'ing and moving out today. Story credit: Reddit / [deleted]

Tampering With The Evidence


This was at a time when mobile internet hadn't caught on yet but the SMS services were at it's peak and they were cheap in our parts. Me and my then GF exchanged loads of SMSes.

It became kinda evident that our relationship was ending. We formalized it much later but we had already known it was headed that way.

Anyway, she shows up with a note book and asks me to check it out. Turns out, she had hand written down every single text message that I had sent to her. That was a good 250 pages long notebook. It was Full!

I wasn't sure how to react so I jokingly said something along the lines of 'This is...weird, are you going to use this as evidence in some way?' She got mad and tore apart the entire book in my face. I don't know why, it was something about the way she did that got me mad. I got up and left.

We meet again later and turns out she had re-written the whole thing and asked me to keep the revised version. I declined politely this time. She messages me a year later that she tore the revised notebook. Story credit: Reddit / PlsDontBraidMyBeard

I Hate Mondays

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I was really young, like fourth grade, and I thought I was in love with this girl. I had just moved to a new state and didn't know very many people and thought I was in love with my neighbor. We were in the same grade and we had the same teacher and she was in LOVE with Garfield.

So I saved up all my lunch money for a week and I went to the book sale (remember those things in school? Best week EVER.) and bought several Garfield books and some gel pens for good measure. The next day, I walk to the bus stop and pull her aside.

I say, "Will you be my girlfriend?" "N-No!" she stammered. "Wait, before you answer," I slowly unzip my backpack. I start furtively handing her garfield books. At this point, several of our friends had walked over to watch the spectacle. "I don't.." "Wait, there's more," start making it rain gel pens up in this witch.

Eventually she explained she didn't want to date me. I ended up reading the Garfield books, realizing he's a funny cat, and enjoying life. Apparently love in fourth grade doesn't last a lifetime. Still have friends who bring up the story though. Story credit: Reddit / Gladiatormouse

The Wind Beneath My Wings


Not me, but in high school I worked at a Canadian Tire with this guy. I forget his name, but he had a Space Invaders tattoo on his wrist. Anyway, we worked together upstairs (it was a really big store) and used to sneak off to smoke cigarettes (and occasionally other things).

One day, just as we're coming back from smoking a bowl in the side stairwell, a voice comes over the loudspeaker asking for everyone's attention.

It's a young girl, and she asks for everyone's attention because she goes on to publicly declare her eternal and undying love for him, her voice echoing throughout Canadian Tire, and then proceeds to sing Wind Beneath My Wings by Bette Midler over the loudspeaker, dedicated to him.

He just took off and never came back to work. It was pretty hilarious. For me. Not for him. Or for her, I'd think. Poor girl. Story credit: Reddit / StickleyMan

Not Exactly Shakespeare


When I was I high school I found out that someone who had a crush on me was writing poetry about me and submitting it online.

The poetry was full of spelling errors and much of it was about killing me or watching me from afar. I don't know why I was one of the last one to fin about it, I have bad friends. Story credit: Reddit / Ddaddy_Long_Legss

Prom Drama Queen


In my sophomore year of high school, my best friend was stalked by a terrifying senior. She was, I'm fairly certain, completely crazy and she was obsessed with him. She'd spend most of her days lurking the hallways and waiting for him to walk around a corner.

One of the scariest moments was when we were walking out of the lunchroom and she jumped to give him a hug. Because I was his female best friend, I was mostly ignored by her.

She ended up asking him to senior prom and, because he did his best to be polite, ended up going with her. Crazygirl clung onto him all night, and forced her tongue down his throat.

After all of this (he wasn't able to go to after prom with her because of a prior commitment) she flipped out at him for not spending more time with her, which consisted of a lot of creepy tumblr 'ask mores' on her blog. She's currently in college in Utah, and still asks him when he wants to hang out with her.

She has 4 pictures of him above her dorm room bed, and he finally blocked her on facebook a few days ago. Story credit: Reddit / kookyslimty

Struck Out


Middle school, 13, fell in love with a girl named Grace. I had been crushing on her since the beginning of school. (This was March BTW) I was talking to her and ON THE NIGHT OF THE DANCE she says she has a crush on me.

Who knows why I teased her about it instead of telling her my feelings. She just left, not sure if she cried. Guess who didn't slow dance that night. Story credit: Reddit / Saltiner

Trophy Date


A guy I barely knew roped me into going to his school's prom with him and proceeded to introduce me to literally every student, teacher, and hotel staff member at prom.

He was clearly, blatantly not well-liked by his peers and everyone was just like "Um, okay? Hi?" A few times he slipped and would say "This is my gir-…friend." …We weren't dating. Story credit: Reddit / AetherTransmissions



Grade 7, just transferred over to a public middle school in my town. I started riding the bus to school and there was this girl who we'll call "Sam". Sam was weird. Sam really (read: REALLY) liked me. My feelings did not reciprocate.

Sam was a lonely, countryish type girl who was into anime. Every day on the bus she had a new poem she would write me. Really good poetry actually, but it was very uncomfortable in the sense that I didn't like her at all.

One day, I decided to explain to her my lack of feelings the nicest way I could. This did not sit well with Sam at all. Things escalated, she started drawing anime pictures of me. They went from normal pictures of me, to pictures of us at our wedding, to pictures of her killing me with a buck knife.

This freaked me out so I told the school counselor. Who pretty much did nothing. The pictures and poems stopped, but every day I got onto the bus she would be waiting at the first seat and loudly make an animal like hiss at me. In front of everybody. Bad times. Story credit: Reddit / [deleted]

The Long Con


I was in eighth grade and on the bus. A sixth grade girl that I hadn't ever really noticed with messy, short blonde hair hands me a packet of 8 pages stapled together. Each page is literally full, front and back, of 'I love you' over and over again. It was kind of cute but horrifyingly creepy.

Flash forward to early college: I meet a hot blonde 18 year old, I learn her name and realize it's the same girl. I ask if she knows who I am before I say my name, she says: "Of course I do, Blake. I love you."

I leave and have done my best to avoid blondes since. Story credit: Reddit / blakezilla

Not So Secret Admirer


Oh dear…high school. She memorized my timetable, knew what room I lived in, and pretty much always knew where I was (then again, I am a creature of habit) I never had the heart to tell her. Story credit: Reddit / Plexit

She Knew


As luck would have it my crush was on the same bus as me. We lived in a rural area so that meant spending 45 minutes together every afternoon.

One day they got to chatting about crushes and possible future boyfriends. My crush jumps around in her seat (she sat in front of me), and playfully asks "do YOU have a crush?!".

"EGADs", I thought. could this be my chance to profess my love for this beautiful girl? In front of her friends and other snot-nosed peers?

"y-yes, I do." I managed to nervously squeak out. "Who?" she asked inquisitively.

This was the make-or-break moment of my life. Tell her how you feel and live happily ever after. Nope. "Well" my brain went completely blank. "some GUY."

As soon as the words came out of my mouth I regretted them. I knew from this point forward I stood no chance. I was now the "maybe gay guy that professed his love for a dude".

Grade 9 grad she singled me out for a slow dance, though. She asked me and everything. She knew. Story credit: Reddit / noocuelur

A Stalker Defeated


I liked this girl. Good start, right? We'll call her Jenny. So we were in high school, and I knew that she had a thing for me. I had a thing for her too, she's pretty hot, but problem was, her ex bf was my best friend. We'll call him Jimmy. So she used to date Jimmy, and I mean bro code, so no can do.

So I ignore it, but guess what should happen? Jimmy ends up telling me one day that he asked my ex (with whom I was hung up over for roughly 3 years before finally getting over... We'll call her Janice.) on a date. Not being the type of guy to pick fights I gritted my teeth and said 'hey, good for you, man!'.

Well, I was kind of miserable about them, but the side effect was that me and Jenny started talking a lot more. A lot more. Like we'd give each other long, definitely-more-than-friends hugs every time we saw each other, and all the usual high school flirtation strategies.

So Jenny and I were hitting it off pretty well as more-than-friends-but-not-quite-"friendly"-friends-yet, and it was a good time for me, but remember how I said I wasn't the type to pick fights? Well that demeanor comes bundled with the package of "never take initiative for anything, ever".

So as you may guess, I never asked Jenny out. I never did anything besides give her a hug and have our usual conversations. So Christmas break rolls around, and that's all merry, but once school started back up, I noticed Jenny didn't talk to me.

I said hi, she said hi, but no hugs, no conversation, no long meaningful eye contact... I wondered what had happened. Well actually I had figured it out pretty quick, it's what happened to every single girl I got even kinda involved with in HS, I pushed them away because they thought I wasn't interested in them.

Like I said, I never took initiative. So Jenny is platonic status towards me now, and since I never stand up and fix problems, I let this situation fester and get worse, until the point where we never even made eye contact anymore.

Well, that's good and all, but problem was, I still carried my feelings for her. So, with the only form of action I could take being passive, I decide to chance a run-in with her in the hallway.

I scope out her classes (wasn't hard since we had walked to all of each others' classes the semester before), and find a place to intersect our paths. I figured if I did that and she saw me, she would initiate the conversation and be flirty so I wouldn't have to do it.

Sounds realistic, right? Well this carried on for more than just one day. In fact, it carried on for three months. Almost every day I would pass Jenny in the hallway, pretending I didn't notice her, hoping she would say hi. I skipped some days just to not overdo it.

It became so bad that sometimes I actually ended up waiting an hour and a half after school and would make up an excuse to be there for when she got out of her musical rehearsal.

I would follow her tweets on what she was doing and chance a meeting there, I would "accidentally" text her deep and thought-provoking messages that made me sound mysterious. Yes. I was basically stalking this girl, and she knew it.

How did she know it? Because one April day of some year, I was crossing paths with her during one of my chance encounters. It was one of my two paths that I actually had to go way out of my way to see her.

Turns out, Jenny had done her research and found out that I didn't need to be walking anywhere close to where I was, especially not for three months.

Her class was on the top floor of our school, the arts and crafts hallway that only had two active classes that year, one of which was at the very beginning of the school day, and I had no art classes. So why was I there?

We passed each other in the crowded hallway. Just as we got to the point where we would leave each other's peripherals, I took a glance, sure that she wouldn't notice me looking at her.

I noticed that her face was turning towards me. I quickly glanced forward, intent on keeping me calm-and-collected and I-don't-care act. I heard my name.

I halted. Turning around, I saw Jenny glaring right at me. Her snap had attracted attention from the fellow hallway marchers. She had clenched fists, and if the human body were capable of blowing steam out of its ears in anger, she would've done so.

"O-Oh hi, Jenny! I didn't s-" She interrupted me with a voice that, while not screaming, was loud and sharp enough to give off the demeaning tone she was trying to achieve.

"Don't you ever follow me again. Since you know my schedule so well, try avoiding me from now on." She gracefully, yet firmly turned on her heel and marched onwards.

The lanyard and ID I was twirling on my index finger fell to the ground. I was speechless. Bracing the whispers of judgement and the blanket of shame falling down upon me, I gathered my belongings and tried to walk to my next class with whatever shreds of pride I had left.

I promptly failed. Never again did I see Jenny in the hallways. So yeah, idk about whoever reads that, but I cringe every time I remember it. Story credit: Reddit / Sharpam

Dragged Out of the Friendzone


First year of college, me and this girl were pretty good friends. We'd have all these conversations, but I had gone out of my way to jump in the friendzone, so I didn't think twice about it.

Then, near the end of the semester, I started hearing the two of us being mentioned as a couple. Apparently, she assumed we were together and started telling people likewise, for two months.

Then, a week later, I hear how badly I "dumped her." Oh well. Story credit: Reddit / kngegypt7

Tee Public


In middle school I made a shirt with that had "I <3 "her initials"' on the front of it. But I didn't have the balls to flat out wear it, so i wore a hoodie over it and told her on the bus ride to school.

By the end of the day everyone knew about it. Yea, I look back and cringe on that one. Story credit: Reddit / CharliePottsSL92

Clutching Defeat From The Jaws of Success


Early in high school, before I had any confidence, I found out that my best friend's cousin had a crush on me. She was really hot, but I always thought about her as my friend's cousin, so I never realized that I had feelings for her (Probably didn't until she said she did.. men are creatures of opportunity).

Anyway, I was in another state for the summer because my parents are divorced and she hits me up on instant messenger. She talks to me every day for a few days, which was weird, because before this I hadn't had very much contact with her.

A friend of mine tells me about 4 days in that he ran into her and gave her my info so she could contact me, and being the superb wing man he is, wrestled out of her the reason that she wanted to talk to me. She told him that she liked me.

This was ideal, because when I have time to think and no insanely hot girl staring at me, I can be the smoothest Casanova in the world. Over the next month, I had her admit her feelings and I mine, but because I'm so smooth.. I decided to not ask her out until I could do it in person. It was going to be great.

Fast forward a little bit, I'm back in the same state as her, everything is going great. I go over to my best friend's house to meet her. My friend isn't there, and she's babysitting my friend's little brother. Let's keep in mind, I'm a freshman in highschool. Have some pity on me. I see her wearing the cutest outfit.

She smiles warmly when I enter the room and my brain melts. I don't know how to talk to her anymore, so I smile back and say "Hey... *look at my friend's little brother* How are you, James?"

And continue to pretty much ignore her for an hour before awkwardly leaving without saying much more than a sentence to her. She immediately called her friends to let them know what happened, which I can't really blame her for.

I was so embarrassed by it, but apparently she didn't understand my awkwardness and suspected that I had been so smooth over the internet and had lied about my feelings about her, so it was all just a game to her.

I couldn't recover from it, her friends were mad at me for being a jerk and she didn't want to see me ever again. I regretted that for a long time, because after all of that I wasn't able to turn it off again. I really liked her now.

I would see her sometimes, because I played a lot of basketball and I would hang out at my best friend's house because it was close to the courts I played at. I like to think that I didn't go to her house (yes, my best friend was a girl) to see her cousin.. but I think I did sometimes.

It was always awkward and always made me regret being such a baby, so I stopped doing it pretty soon after. I'm not sure what the source of my nervousness was, even to this day. I always suspected that I was awkward because I was afraid of rejection.

That couldn't possibly be in this case.. because I KNEW with certainty that I wouldn't be rejected. She was more into me that I was to her.

I'm happily married now, but I still view this as one of the two events that I regret in my lifetime. The other was much worse, but not really along the lines of this question. Story credit: Reddit / perfectdesign

Horsing Around


I was in a PSAT room with this guy that I knew had liked me for about eight years at that point (we met in our third grade class). I was eating an apple &, in his nervous desperation to talk to me, he decided that a great conversation starter would be "Hey. You look like a horse."

Needless to say I fell head over heels & we've been together for two years now. Story credit: Reddit / [deleted]

Birthday Rejection


When I was 15 or so, there were these two girls in my neighborhood that apparently had a crush on me. I had no idea at the time. On my birthday, they show up and give me a card and wish me happy birthday.

I just said "Thanks!" and went on with my day, not because I was mean or anything, just that I was that oblivious to what was going on. I still cringe over how much of an ass I was and how stupid I was for not understanding the situation.

I probably crushed those two right then and there and never reflected on it until much later in life. If this sounds familiar to you and you lived in Montana around the 90's, I'm so sorry and thank you for your thoughtful gift. Story credit: Reddit / Shirosynth

Cheater Disaster


Back in high school, I really liked this girl but knew she was way out of my league for many reasons and the fact that she had a bf and I'm a lesbian, so I never pursued anything more than a friendship.

So one day, she randomly texted me during our class, she's sitting to my right a few seats down; "Have you ever kissed a girl in the bathroom?"

I look over at her, she smiles, gets up and walks out of class... At this point, there are a millions things running through my mind; like is this really happening? Is this a trick? What is happening!?

So I very calmly walked out of class about 3 minutes after she did. Halfway to the bathroom I stopped, turned around and decided to go back to class. I got very turned off by the fact she would cheat on her bf of 3 years!!!!!

....but weeks went by and I couldn't resist any longer. We secretly dated for awhile. It was great until she broke my heart because she wouldn't break up with her boyfriend!!!!! Story credit: Reddit / Pineapples91

Not Playing Along


So, back when I was a freshman in high school there was this girl named Britany (not her name) had a crush on me. She was sweet and pretty, I just wasn't into her. Anyway, she asked me out for dinner, I said as friends, she reluctantly agreed. We talked about cartoons the whole time. Had fun as her friend.

The next day at lunch, in the cafeteria she comes up to me and asked if she could take a picture of us like a couple so her parents think we are dating. I decline on the grounds that we are just friends and that it's very creepy.

I don't think she heard me because he sits right next to me, points infront of me, I look up, she kisses my cheek, and I see a flash. She set this whole thing up. Side note, back then I would smile all the time, especially when nervous. And I was nervous.

Later that day,after school, while at home the phone rings, it' her mom wanting to talk to my mom about us dating. My asks if I am dating anyone, I tell the truth, hell no. She asks about the picture, I pick up the phone and explain the whole like I'm talking to a child.

She understands, says goodbye, and hangs up. My mother calls the girl crazy and goes to the living room. All this was on Friday. That Monday I didn't see her. Tuesday comes and goes without showing up.

Wednesday she comes up to me in first period (she's not in that class) and says I messed it all up and should have played along. She storms out leaving myself and the entire class stunned and confused.

I haven't seen since then. Part of me feels bad, other parts feel like I doged a crazy missle, and now most parts feel indifferent. Story credit: Reddit / [deleted]

Getting It Off Their Chest


Briefly dated this girl when I was 17, it didn't work out; I broke up with her, her friends egged my car... all the usual teenage fun. She almost immediately starts dating another guy. About two years pass, and I'm just out of a long-term relationship.

She's still dating this same rebound guy, but I can tell she still has feelings for me, so of course I use that as a massive confidence boost and hang out with her all the time even though I'm not interested in dating her again.

One day we're hanging at her place, and our usual flirtation escalates to some play-fighting. Yeah, highway to the danger zone... not wanting to be that guy (even though I was clearly already being a jerk), I hastily leave after we almost kiss, and avoid her for a few weeks.

So, a few weeks later, her boyfriend texts me asking if we can chat. Neither of us are the violent type so I sheepishly agree, ready to apologise profusely and promise to stay away. Instead, he leads the conversation with, "So, obviously you and my girlfriend still have some feelings for each other.

Do you just want to go out so you two can get it off your chest?" I still haven't decided if he's the most whipped guy or the most incredibly confident guy I've ever met.

I later found out that she had packed up his stuff (he was living with her) expecting me to ask her out, but when that never happened, they stayed together. So I'm going to go with whipped. They're married now. Story credit: Reddit / [deleted]

You're Hair


In high school a guy wrote me a poem listing all the parts of me he loved... the problem was, he couldn't differentiate between "your" and "you're" and the entire thing was laid out like: You're lips. You're skin.

You're hair. Really dude? Am I hair? Story credit: Reddit / SeaOttersHoldHands

Beneath the Surface


A horrifying chapter of my life unfolded back in high school when I was kidnapped. I spent a week in a chilling nightmare but managed to escape my captor's clutches. I reported him to the police immediately, but he was never found. Life had to go on, and so I did my best to move forward, but the trauma of the past always lingered.

Fast forward 10 years, my high school crush, the one person I had always admired, invited me over to his house. Elated, I accepted his invitation, unaware of what awaited me. Upon entering his house, I was struck by a wave of chilling familiarity. My heart pounded in my chest as I spotted an old picture. I held it up, my hands shaking, and managed to stutter out, 'Why do you have this?' His response was a chilling smile that turned my blood cold. 'Took you long enough, sweetie.' he smirked. My heart dropped, and a horrifying realization washed over me.