Some people take the subtle and sweet approach, while others just get straight creepy.
Work Release Romeo

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My work started using a program that began hiring ex-cons. One of the guys hired through this program started showing interest in me. I wasn’t attracted to him at all and made it clear to him…repeatedly. Long story short he got fired 3 months later but kept coming around the store “to visit his friends”. I go out to my car to read during lunch like normal and there’s a creepy metal and mesh flower on my windshield. I look around the parking lot to see who could have left it and see no one. I threw it into a grassy area and forget about it. I read through my lunch hour and go inside and no sooner than I clock in I hear a page that I have a phone call. It’s him. All he says is “You look so pretty when you’re reading”. I hung up immediately and told the manager. He kept doing more things that escalated the creepiness. I ended up getting a emergency restraining order against him when I found out he added me as a emergency contact with his parole officer. I didn’t even know him!!! (Source)
The B&B Creeper

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I managed a cafe that was located about an an-hour-something drive from my house. There was this guy who had it really bad for me. He came in a couple of times a day and refused to be served by any of my staff, just me. Anyway, as if that wasn’t bad enough… One day during the winter it got very icy, so I decided to not drive home, but stay in a B&B instead. Safety and sh_t. Don’t ask me how, but he found out and stayed in the same B&B. Was woken up by him banging on my door. When I open he stands there fuming about how I don’t trust him or why else would I lock the door to my room during the night. Now, who doesn’t lock the door in a B&B. Also, well… D’oh. Guess what? He obviously tried the door. What the what? Also, by the time I made it to work the next morning (2 minute walk from the B&B) he had already managed to tell a good portion of the townies we had spend the night together. This guy actually scared the crap out of me. I regularly passed up other people working on the same street to not have to walk to the parking lot alone. (Source)
Sharpie-crazed Stalker

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During camp once I overheard of a girl who was into me. I wasn’t that much of a fan of her so I didn’t 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 didn’t know how to react, I just ran away.. I bump into her here and there nowadays.. It’s still extremely awkward. …(shivers) (Source)
Baby Boomer

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She used to send me baby photos of herself with captions like “you want some of this don’t cha” (Source)
The Obsessed Overlord

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When I was 14, I started hanging out with a kid at school that others called creepy (I think mainly because he wore a trench coat every day). I didn’t think he was creepy, so I befriended him. We chatted online after school for a few weeks, but he started acting more and more obsessive, until one day he told me in a chat that he wanted to come to my house, tie me to my bed and rape me. I freaked out and stopped talking to him immediately. After several weeks of me ignoring him at school, he emailed me a link to his fan fiction page, where he had written a 20+ chapter story about us, in which he was a Wolf Warlock Overlord and I was his helpless human sex slave. At this point I probably should have told my parents, but I hoped it would all go away if I ignored him. Soon after he came to school with a backpack full of weapons and explosives and was expelled. (Source)
Gothic Greg

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Oh boy. Greg. Greg was this weirdo guy at my school who was 2 years ahead of me. Let me paint a picture: short and skinny, with a lazy eye and a huge ass scar on his neck from a trachea procedure, super-duper gothed out (this is like, 2004-2006), black gloves with safety pins everywhere, sometimes wore a Phantom of the Opera mask to school, etc. Last time I saw him on any kind of social media, he was wearing a red silk cape in the profile picture. You get it. He was in my health class. He was weird, but he seemed harmless, and my health class was full of dickheads who’d pick on the kid for no reason, and little baby freshman me thought she needed to be super nice to him to make up for everything. Didn’t think much of it, just, you know, tried not being a dickhead. Well. Come springtime, I walk into the journalism lab and sit down at my computer to find – what’s this? – a NOTE under my mouse. All of my friends are curiously gathered around me, and I read: “If you’re reading this, it means I didn’t have the balls to ask you in person, but… annnnnd thus begins the note where he asks me to prom with him (this is like, MAYBE 10 days before prom, btw). Apparently, he’s been in love with me the whole semester and had even changed around his class schedule to not only be in another class with me, but also SO HE COULD PASS BY ME IN THE HALLWAYS. I tell him no, sorry, I had already planned to have a sleepover at my friend’s house that night (I was 14, okay? I didn’t know any better!) and as far as I’m concerned, that solves it. I don’t hear from him much after that. The next year. No classes with him, barely any contact – until one day, about 10 days before prom, I’m walking out of my journalism class. BOOM, there he is, right in my face. “Hey, do you want to go to prom with me this year?” This time it’s easier. “No thank you. I’m sorry.”
But hey, it was his senior year and he’d be graduating and I’d never have to see him again, right? Great! Oh, he’s joining the Army? Well that’s…nice? Basic starts a month after graduation? Well, I wish him luck. And then, I was free. No Greg. Not even a thought of him. UNTIL – my junior year. I walk into the cafeteria before school one morning and there. he. is. Looking as gothy and weird as ever. He starts walking toward me, I make a dash to the girl’s bathroom, pretending I didn’t see him. My school didn’t really allow visitors, so I was sure that he’d be gone soon.
And then that afternoon I’m sitting at lunch, eating with my little sister and a group of our friends. I had considered eating in the bathroom Mean Girls style just in case, but…no. He walks up with tears in his eyes. Asks to talk to me for a second. Sure. In front of everyone, he tells me he has something for me. Whips out a stack of 30-something letters he’d written me in basic training. Tells me he loves me and that he’s deploying to Afghanistan next week. Wants my address so he can actually send me the letters. He’s openly weeping. I take the letters, write down my address real quick, and go spend the rest of lunch in the bathroom. I shouldn’t have opened those letters. Oh my god. They were…graphic. They were NSFW. They detailed what our children would look like, where we would live, our careers, our retirement together.
They were all like that. And guess what? Guess who DIDN’T deploy to Afghanistan – hell, guess who didn’t even finish basic training? About a month after that incident, he messages me on MySpace, apologizing for being a weirdo creep. I wrote back saying something like “Don’t worry about it.” The next day, when I come home from youth group or wherever I’d been, my mom hand me the phone. “Someone named Greg has been calling for you? He’s called here 25 times in the past 2 hours. You might want to call him back.” And I did. I told him off, asked him not to contact me anymore, etc etc. I was pretty pissed. Last I heard from him was when I googled my own name and found a MySpace note he’d written detailing his intense hatred for me and why I’m a stupid cunt who needs to die, and HOW I need to die, and so on. (Source)
Sometimes You’re the Windshield…

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In high school I had 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 was a freshman, and the girl in question had a HUUUGE crush on him and 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 calm 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… “Hey Guys! She runs headfirst into a parked car and f_cks 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 because 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, just to talk sh_t. But Sean and I knew what happened, and I still cringe every time I visualize her eating windshield… (Source)
Below the Belt

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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 right in the vagina and walked away. (Source)
Toe Jam

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Well, once I got drunk and banged a rather unattractive woman. Much to my chagrin, she got a little clingy. So, some friends and I were out and she showed up, no big deal. We all go back to someone’s place for the after-bar. I pass out on the couch. I wake up in the morning and she is on the recliner near my feet. My foot is under her blanket. She has placed my big toe in her vagina. I pull it out. It is bloody. No idea where my sock or shoe is. I go home in January with one bare foot. (Source)
Taking Notes

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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 sh_t 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 pissed 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 pissed. 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. (Source)
The Jerk

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When I was about 16 a friend/client of my mother’s was at our apartment a lot. He had been acting strange for about a year. I tried to avoid him but sometimes he was unavoidable (eg, one night he came into my room when I was in bed to say goodnight to me). One evening I was in the kitchen and he came to say that he was leaving. I picked up the nearest book (Joy of Cooking) and pretended to be very interested in it. I nodded and said goodbye. He stood there a minute and then kissed me on the mouth, sticking his tongue in. It was really gross. I repeated goodbye and tried to read a recipe. He left and I took off out the fire escape, finding my cat and trying to stop freaking out. I went to the back of the apartment, and he found me there, and asked if I would go for ride with him. I said no, that we didn’t have anything in common, and he was at least 10 years older than me. “But you are so mature, and I am immature” like that was some kind of inducement. Then he told me that it may not seem like a compliment now, but it will later – that when he masturbates, he thinks of me. Funny, it has been 30 years, and it still doesn’t seem like a very good compliment. (Source)
Anime Admirer

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My time to shine. 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, country-ish 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 the f_ck out so I told the school counselor. Who pretty much did nothing. The pictures and poems stopped, but every damn 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. (Source)
Energy Fighter

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Dated an Asian…think we met on Myspace?? (2007 holla) anyway, this kid was completely ridiculous. He wore tripp pants out, he thought he was some shadow warrior who was like 10,000 years old named “Xin” and he and his ‘brother’ (another tripp pants guy, no relation whatsoever except of course his reincarnated brother) used to “fight” with “energy” so they would like, push air at each other and sh_t. So this went on for awhile, I broke his heart after a month of this hilarious stuff, and then he came into my work looking for me….like a 45 minute out of the way drive from his house. I hid –I know, lame– and he then assumed that a demon had overtaken my body and that I was lost in the spirit world. He texted me promising “spirit me” that he would astral project and find me and help put me back in my body. And he warned the demon IN my body to watch its step because he had ‘a lot of very old and powerful friends.’ Few months later I got Facebook curious and he married a fat redheaded wiccan girl. (I was a redhead.) So I guess he found spirit me but had to go for a different body. The demon was just too strong. (Source)
Prom Night Parasite

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It was prom night and my group of friends were at a big party on a lake. There was a girl there who I had a crush on the year before (we went to prom too) but I had moved on at this point. As the night progressed I kind of felt like she was following me around the party but I didn’t want to think much of it because that’s crazy, right? 3 drinks later she is definitely keeping herself within 5 feet of me. She’d follow me to get a new drink, to play a drinking game, ANYTHING. If I noticed her at any point she’d just play it off like it was just such a coincidence that we kept running into each other. Like, it sure was convenient that she followed me outside to go take a piss because girls do that all the time. (I would have taken the hint a long time ago if I was still attracted to her.) Our collaborative group of friends start taking notice of her stalking skills and make it a point to ‘hide’ me from her. I got up quick to leave the room, my friends set a pick for me, and I got out of sight around the corner. I ran outside, around to the back of the house and went upstairs where I had another friend waiting. Then I heard her. “Where’s John?” “Has anyone seen John?” Her cries got louder and louder until she was screaming and crying. No one knew how to handle the situation and she was causing quite the scene so I opted to show myself. As soon as I walked downstairs and into the room she latched onto my leg like a freaking parasite. She had her legs around my ankle and her arms around my thigh. She refused to let go. When I tried to get her off of me she started crying “Why won’t you love me?!” and similar things repeatedly. I don’t remember how but we got her off of me, but I proceeded to drink the night away. My friend had sex with her that night. (Source)
Grammar Challenged

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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? (Source)
Romantic Roomies

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This is currently happening in my life. Girl I met online and really hit it off with came over and stayed the weekend with me after having several previous dates. We agree to start a relationship, because we both like each other. Sunday night comes along, she doesn’t leave.. Monday, she’s at my house after work, I let her stay one more night. Yesterday I ask her to leave because I need space, she tells me she’s in love with me and she never wants to leave, cries uncontrollably because she hates living with her roommate, proposes that she moves in with me immediately. So much nope. (Source)
Spray Can Seduction

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High school, 15 year old male. I somehow manage to be the only Freshman in my foods class. For some reason I figured everyone would see it as a blow-off class, and it would be a nice mix between males and females, but I was very wrong; all girls. I noticed that one particularly heavy girl kept looking at me from the other side of the room. I’m not here to rip on her, but she was not a beauty, and she also struck me as not very popular from her attire, and disposition. If I recall correctly, we were making pumpkin pies, so there was obviously an abundance of whipped cream (in a can) at her disposal. I am getting nervous at this point because she is so ruthlessly staring at me, so I risk one more glance at her. To my horror, this chubby girl has in an attempt to appear sexy and seductive, picked up the can of whipped cream and is filling her mouth with it. This was accompanied of course by the all too familiar “kwwwwsshhhh” sound the can makes. Our eyes are locked as she proceeds to stick her finger in to her full mouth of whipped cream and starts tracing it around her lips. I am a recent college graduate, and I can say that this was the only time I have ever dropped a class in my entire life. (Source)
Dude Looks Like a Lady

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Short story: I’m a lesbian and I was always very open about it, so all my friends know about it. One of my closest friends, a 6 ft. tall, hairy guy, came once over to my house. I opened the door and let him into my apartment – He was wearing a mini skirt, a skin-tight T-shirt and lots of make-up. Before I could even say anything, he burst into tears, told me that he loves me, that he is showing his feminine side just for me and that I would have to be his girlfriend after it was so embarrassing for him to walk like this through the streets. Yeah, um … no. (Source)
Long Lost Beatle

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In the 8th grade, the boy in my class who had been asking me out on a regular basis got up on stage during assembly, proclaimed he was dedicating a song to me, and proceeded to sing Strawberry Fields Forever. Badly. With interpretive dance. (Source)
The Googler

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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. (Source)
Burning Love

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In high school, I started dating a girl a few days before I went to visit family for Christmas vacation. She called me to let me know that she had carved my initials into her ankle with a hot safety pin. (Source)
Funeral Folly

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Had a girl who has, apparently, had a crush on me for fifteen years hit on me… At my wife’s funeral. Not sure how to handle that. (Source)
Don’t Jump

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A girl told me she was going to jump off her roof if I didn’t date her. Her house was only 2 stories so she would’ve only sustained broken legs (and heart; buuuurrrn). I didn’t date her. She didn’t jump. Awesome story. (Source)
Heartsick Hood Ornament

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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. She hasn’t let me live it down yet. In fact, its a topic of conversation when we have guests over. (Source)
Cookie Crush

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In 7th grade I had this girl who was absolutely obsessed with me. Everyday after lunch she would walk over, hand me a bag of cookies, say hi, then leave. I’m talking perfectly undercooked, warm, double chocolate chip circles of heaven. Now, I wasn’t interested in her at all, but I mean c’mon… I wasn’t about to put an end to that. It was delicious for me, but she must’ve spent at least $200 over the course of the school year. (Source)
Unhinged Hero

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A guy I knew in high school and worked with at a restaurant told his best friend that he wanted to wear a mask, kidnap me with a sheet and put me in the trunk of a car. He would then park the car somewhere and fake my rescue. That way he could be my hero. So that still haunts me a little. (Source)
Bumbling Bieber

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I recently received a voice mail from a guy I dated briefly. He broke things off before I went to London for a month because he couldn’t commit. (I came back from London 2 years ago) “Hi you’re back from London now…. and I’m ready to – you told me to call you when I’m serious… and I’m serious now… Dead. Serious. Sooo I’m ready… to be your boyfriend because- If I was your boyfriend, I’d never let you go I can take you places you ain’t never been before Baby take a chance or you’ll never ever ever know I got money in my hands that I’d really like to blow Swag… swag…” If you were wondering the last part of that drunken voice mail was a rapped excerpt from the classic “Boyfriend” by Justin Bieber. (Source)
Courthouse Creeper

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Meet this guy first year at uni. He’s a little awkward, but he’s interesting to talk to. Well, about mid-term he asks me out on a date. I don’t really find him that interesting but agree to go because I’ve never been formally asked on a date before and he seems to be a pleasant enough guy. Picks me up for our date; while on the drive he proceeds to serenade me in hardcore heavy-metal gibberish. Okay. Weird but whatever. He goes to drop me off after and we start talking, when he says he has to confess to me that he’s going through court and could potentially be legally determined to be a sex offender for rape. That was a deal-breaker to say the least. (Source)
Perfect Proposal

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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… (Source)
Why the Long Face?

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I was in a PSAT room with this guy that I new 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. (Source)