Crushes can either be really sweet or well, really, really creepy. These people share the most awkward crush someone has ever had on them.
Boss’s Favorite
“I’ve been working in an insurance agency for about 2.5 months. For about 2 months now my boss has been acting very “affectionate” towards me. By that, I mean she’ll call me a dork in a flirtatious manner, one time she told me that if I stayed late she’d buy me dinner, she’ll slap me playfully when I say something mildly witty, when I show her something on my computer she’ll kinda lean on the table but lean on me also a bit at the same time, and she’s recently started a habit of affectionately punching my arm. It’s making me feel really awkward and I don’t know what to do about it. But it’s okay, as long as the fact that she could be crushing on me means that I have an easier time at work.”
Family Secrets
“My cousin once had a crush on me.. She was 2 years younger and when I was 20, she saw something on a movie where the girl waits on a bed naked and waits for the guy to come in.. So when I was coming home (I live with my grandmother) she came to my grandma and she waited on the bed in only underwear, nothing on the top.. However, my grandmother failed to mention that I was bringing my college girlfriend for the weekend.. As I was unloading my grandmother offered to show the room that my girlfriend was going to sleep in. However, they opened the door to my cousin who screamed profusely.. Awkward..”
A Brutal Love Triangle
“I was part of a very awkward love triangle in grade 6.
I had a crush on a certain girl. So did the kid with Down’s Syndrome.
In June of that year, there was an overnight school trip to a summer camp. Down’s Syndrome kid thought girl and I were dating, so he forged a break-up note from her to me and left it in my bunk.
I was not fooled.”
A Shameful Rejection
“When I was around 14, a girl with a pretty severe physical deformity that resulted in bulging eyes and arms that didn’t really extend, started very obviously hitting on me, in front of all of my friends. I didn’t know what to do; she was a really nice girl but I was just not attracted to her at all. I quickly asked some other girl to be my girlfriend, and let her find out about that. She was upset.
I felt really bad, because due to her deformity I had seen her as a child, and I realized for the first time that she was my age and had the same teenage desires, and how I was just the first of a long line of guys who would reject her because of the way she was, and how it was just so unfair.
I don’t like thinking about this.”
Creepy To 100 Real Fast
“During my time in a uni share house, I lived with a 19 year old guy while I was 29. After knowing me for a mere five days, he asked if he could paint me naked and even though I said no, he proceeded to tell me he was in love with me. I immediately went to get moved to new accommodation, because things got creepy fast. While I was gone he left a suicide note on my door. He disappeared for 24 hours. I was interviewed by the police.”
Get Out Fast
“In my early twenties when my girlfriend’s sister, who was a very well developed 16 year old, goes crushing on me hard. Even got my number out of girlfriend’s phone to text me at all hours.
It was awkward as h—, the gf didn’t listen, and said she was just being playful. The gf shared everything with the sister. So I ended it all when I received a text in the middle of the night from her sister, as I was laying next to the gf shortly after sex with her, who was sleeping over at the gf’s apartment and in the living room that read “I want you to make me c– the way you make my sister.”
Not My Type…
“This girl had a crush on me once, I told her I wasn’t a lesbian and she didn’t think that was a good enough reason.”
Drunken Stupor
“Friend’s mom used to get drunk when we were hanging out there and try and sleep with me.”
Pleading The Fifth
“I’m not sure if it was just a joke or what, but there was a rumor going around back in high school that the female equivalent of a neckbeard had a vibrator named after me that was the centerpiece to a shrine of me. I asked one of her friends about it, and she would neither confirm nor deny. She did, however, confirm that the girl had an obsession-level crush on me.”
Going Down The List
“I was in high school, sitting in art class when this guy walks over. I didn’t particularly like him or not like him. I didn’t know him that well. He stops at my table and casually asks for my phone number. I say “Sure!” and he pulls out a piece of notebook paper filled with phone numbers…all suspiciously the numbers of nearly every girl in our grade. It was too late to say no and I got a phone call from him at least a dozen times a week for a month. The fact that no one ever picked up (save for the first time….boy was that an awkward phone conversation) never stopped him. I just pictured him calling down that list every day.”
Still Waiting
“My best friend came out as gay and then proceeded to tell me how much he liked me. He knew I was straight, but decided it would be appropriate to straddle me whenever I sat down around him. Still waiting for it to stop.”
Way Too Much To Handle
“In eighth grade I was stalked for several months by a girl one year younger than me.
At first it was rather benign, we ate lunch together in our group of friends and hung out a few times after school. She seemed rather interesting if a little odd.
Then it started getting more creepy. She decided to read me some of her short stories which involved me tearing off her dress and raping her. I was called into the principal’s office because she decided to share one of them with her English class.
After that I decided I wanted nothing more to do with her but it just got worse. She started calling my home at all hours of the night and even stood in my front lawn from around midnight until 3 a few times. She just stared at my house. I can’t exaggerate how creepy it was.
She started writing hate mail to all my female friends saying they were c— etc and we got seriously worried she would do something to one girl in particular(this girl wasn’t actually one of my friends, she was just dating a boy with the same first name as me).
It all ended once I went to high school but she did the same thing to several other people before she was expelled. I don’t know what has happened to her since.”
A Secret Love
“My friend’s (at the time) fiancee was a little bit in love with me. That was an awkward period of time…”
Let Her Down Easy
“I had a stalker. Not even kidding, or well… as much as you can call someone a stalker in High School. I always treated my “stalker” with respect (Even though it was weird), she would follow me around school, give me these love letters, draw pictures of us together, make me these home made bracelets and necklaces, call me up at the most random times she even had my private email address. I tried to let her down easily multiple times but she didn’t give up. One time she appeared at my house crying, I had to take her in and stop her from crying. She would occasionally call up crying and I’d have to talk for hours on end to try and calm her down. One day I just had enough, so I told her as directly as possible (while still trying to be nice), “I’m sorry, but I’m not interested okay…?” She disappeared about a month later, moved country, school etc. Two years later she came back, I added her on Facebook and she told me she was sorry, talked to her a while and she seemed to have lost her craziness, she now has a boyfriend.”
How May I Help You?
“I run programming courses for a living for a well known IT college in my country. Part of my agreement with said college is that they can give my phone number to students who have slightly more technical questions than their marketing staff can answer. I get a call from this female potential student one day, and I answer all her questions during the phone conversation. 15 minutes after we hang up I get an SMS asking if I’ve got a LinkedIn account. Fair enough, legit question, I send back a message with my LI address. A few moments pass and I get another message, saying “but you don’t have a picture on your LI profile”. I answered saying I keep my pictures on FB. I instantly get an FB friend request from her (FB address is the same as my LI address). I approve, going the extra mile to get this girl to sign up for the course. The following days I get bombarded with personal FB messages about life, likes, dislikes and such – every day, non stop. I answer less and less frequently, up to a point where I just stop answering at all. A couple of days later, she calls me up again. I figured she wants to talk about the course because otherwise calling me would be pretty damn inappropriate.
The call went something like this: “Yes Jessica, what can I do for you?” “Well, I just thought it’d be easier to talk on the phone rather than on FB” – No s—, I’ve stopped replying to your messages on FB. The phone convo takes a sexual turn super fast, when she asks: “So can I come over?” “No.” “Will you come over here then?” “No.” “Then how will you measure my breast cup size with your hands?”
And that is by far the most awkward crush I’ve had on me.”
Teacher’s Pet
“When I was a sophomore in high school (about 14-15) my chemistry teacher had a really big crush on me, combined with a severe foot fetish. He would polish my boots and offered a foot massage once, but I was too weirded out by that time to accept. I was involved in the school play at the time and he would come in during our rehearsals and loom in the doorway. When he found out I was transferring out of his class (because I couldn’t handle being around him,) he found me in the drama room and confronted me, asking “Why? I just want to know why!” repeatedly until I asked him to leave, at which point he went to the lunch room to sob.
A very uncomfortable crush.”
Lying Through My Teeth
“Not me but my brother had a really unattractive girl after him through high school, I was like 11 and would always answer the phone. I made up increasingly ridiculous excuses and tales of where he was, partying, doing cocaine, heading to a major drug deal, on vacation in Japan, training to be an assassin, it was fun at first but it got annoying pretty fast. He still doesn’t know how she got our number.”
Avoiding A Mess
“I was getting over a stint in the hospital and dropped a lot of weight and muscle mass during the stay. I needed to monitor my health and diet carefully so I was signed up for a program for personal fitness training and meal planning. It helped immensely and I ended up feeling better than ever down the road. However, my PT halfway through became a bit too observant with my progress.
He’d make breathless observations about my legs and hips, then stomach. I thought it might have been crossing a line of some sort when he starting becoming more “detail oriented” in measurements. He told me the truth one day that he felt like I was his project and that he became seriously fond of where I was going physically. I really could have ended his job right then and there and save myself some dignity, but like the raunchy fool I am it just turned me on. I didn’t indulge in it however, but backed out of the program quietly before I got myself into a mess.”
As Far As It Gets
“My boss proposed to me – twice – back when I was living in Japan. I quit the second time.”
