You’re Not The Only Awkward One: 50 Singles Reveal The Most Embarrassing Way They Chased A Crush

1. I have this bad habit of sending Snapchats to the wrong people, and everyone knows this about me. So I’ll sometimes purposely send a wrong Snapchat to someone if I want their attention. Like I’ll get dressed up and send a Snapchat like, “Is this cute for a lunch date?” to the guy I like in order to make him jealous and when he replies I’ll say something like, “Omg that was for my other friend sorry!” It’s so cringey.

2. Early college years. She mentioned off hand that she was reading the Hunger Games. So naturally I read the entire trilogy and then tried to bring it up in conversation. She wasn’t into me and that certainly did not help.

3. I started smoking. That mistake lasted 15 years after 14 year old me moved on from that crush.

4. I’m not proud of it but … I used to work IT for a company and had a huge crush on a woman that worked in one of those group cubicle open office designs, so I purposely sabotaged the computers around her so that they’d call me to come up to fix things.

5. Purposely avoided talking to her. Still know her now, still kind of have feelings for her now, still rarely talk to her.

6. Post dumb IG stories just to see if she viewed.

7. I wore this gorgeous floor-length lace dress to his World Cup party. Everyone else was wearing sports jerseys, and he was there… with his girlfriend, who I didn’t know existed.

8. I liked a boy in the seventh grade. Every day I would buy a Gatorade and pretend I couldn’t open it and ask him to. One day I did open and panicked. I tried to close it again as tight as I could and give it to him to open it for me. He called out on how easy it was to open and looked like it had already been opened. I wanted to climb under the bleachers.

9. Pretended that I didn’t give a shit about them or that I was madly attracted to them. Played it “cool.”

Guess how many times it worked? None. Still doing it at 21.

10. I’m running a 5k tomorrow for no other reason than she is and I’m going to have a heart attack…

11. I was awkward in high school around girls and when I finally got a job I tried everything I could to meet or interact with them. Ended up working at a video store and met a very good looking girl checking out a movie. I pulled up her number from the system and called her after I was sure she was home and asked her out. As soon as I started the conversation I knew I had crossed a line but I tried to keep going.

It’s been years now but I still feel like a creep for doing that.

12. Became a fan of Aerosmith because he used to wear an Aerosmith tee shirt all the time. This was around the time “Get a Grip” came out, so like mid nineties. To this day I change the radio station when Aerosmith comes on.

13. Threw my hair at them. I had really long, bushy hair, and I would get close as I dared and throw it at them so it’d hit them. I think because of all the shampoo commercials where the guy was rubbing the hair of the girl I thought guys liked hair.

14. My crush was a kid who lived down the block from my house.

I stole his dog from his yard and then went to his front door to return it and get to talk to him.

He said he saw me take him out of the yard. I avoided him after that.

15. Once I was was 14 I “accidentally” sent a picture of me in a super fancy dress to my crush because I wanted him to ask me to the dance.

16. Back in my 20s I had the hots for a girl who worked the register at a book store I frequented.

For a few weeks in a row I bought more books, magazines and newspapers than I usually would.

I finally got the courage to ask her out, while paying for a purchase, while a few people were waiting behind me in line.

She said “thanks, but no thanks”.

That was the hardest walk away from a register I ever had.

17. Died my hair black. Already had the long on top high and tight going on, this just added to the bullshit.

18. Like their instagram photos from years ago and re-like them every day.

19. Leaving flowers on her car before she knew my name…

20. Freshman year of college I only knew my crush’s first name. Should I ask somebody what her last name is? Nah, I’ll just spend an entire weekend going through the entire student directory looking for the “Ashley” that lived in my dorm. … Didn’t find her.

21. Tried to start a fight with a dude she was more interested in.

22. Wrote a poem and put it into the school newspaper as filler for some white space we didn’t have ads or copy for. Swore up and down to my crush that it wasn’t about her. It was totally about her.

23. Being a typical weird teenage girl super into wicca in high school I decided the best course of action was to make my crush a maaaaaagic charm that would make him fall in love with me. I made a pouch out of half a book sock, filled it with spices and wax drippings and tied it together with dirty old shoelaces of mine. I gave it to him and said it was a lucky charm to help him get good grades. A month later he fucked my best friend.

24. I messaged him multiple times on Facebook going “Hi. Oops, wrong person!” Each time he was polite about it, but I’m sure he caught on. I look back and want to smack my younger self in the face for that.

25. Freshman year of college- crawled into his bed (top bunk) while he was sleeping.

26. High school. I brought a mirror to school so I could stare at the guy on the down-low, except he immediately noticed and pointed it out to his buddies sitting next to him. Then at break time he told me to stop staring at him, and subsequently avoided me like the plague.

Felt bad, man.

27. The 17-YO sad and awkward me basically fell straight into the friendzone. I did too many cringy things to list, but here are a few instances:

I thought if I made my self indispensable to him, he’d eventually fall for me. So, I basically journaled all of his coursework, for the entire term, on the day before submission.

Later that year, he got drunk and called me. Somewhere in the drunken rambling he casually said “love ya”. You’d not make a deal of that right? Wrong. I called him the next day to remind him he said this, and that’s not all. I then followed it up with.. I love you, too.

YEP. So, an awkward conversation later I went on to avoid him for the next year or so.

28. I looked up where she lived and casually talked about the name of her street. When she said she lived on that street, I acted surprised and was like “Wow that’s really weird haha.”

She knew.

29. I watched 4 seasons of a shitty show she liked.

30. I was pretending to read my now-boyfriend’s palm while we were at a party together (we were pretty drunk). He asked me what one of the lines that I’d skipped meant and I was like, think fast, and said, “Oh… this one means you’re really into the guy to your right.” I was trying to be smooth but was drunk af and forgot I was sitting to his left. Thankfully, there was no competition on the right side, and bless him, he thought it was funny.

Somehow, he’s been putting up with this kind of shit to this date.

31. I had a huge crush on this girl in my health class in high school. I so badly wanted to hit on her but I couldn’t find the courage to do it. One day, I concocted this brilliant plan to finally tell her how attractive she was without coming off weird. During class, I whispered to her, “Hey, my friends are betting me four dollars I won’t tell you how hot you are out loud. I’ll give you half the money if you let me do it.” She gives me a bit of a weird look but agrees. After class, as we’re walking out, I get her attention, and audibly tell her, “Wow, you’re lookin’ so hot today.” Audible enough to give off the impression “my friends” were watching this cringeworthy exchange take place. She awkwardly thanks me, I slip her two dollars, and we part ways. As you may have correctly guessed, no one had bet me to call her hot…and I had just paid a girl two dollars to compliment her out loud. Cringe.

32. In high school I tried to deep throat a burrito in front of my crush. Idk, 14 year old me thought that would be sexy or something? Cue me choking horribly for about 5 minutes straight while trying not to vomit, tears streaming nonstop down my cheeks, and half of a spit up bean burrito from Taco Bell all down the front of my clothes.

Freshman year was a tough one.

33. In an effort to get him to notice me (Junior year of high school) I baked over 200 different Christmas cookies and brought them to school the day before Christmas break started and walked around handing them out to anyone who wanted them all day. He wasn’t in the class that we shared. Found him at lunch and offered him some cookies. He didn’t want any.

At least I was very popular at school for that day, albeit weird.

34. I guess it’s not as bad as the rest, but my cringiest story actually worked, so…

Anyway, first day of orientation week at university, my friend tells me that there’s this guy I have to meet. She just met him because they live on the same floor in residence. She’s convinced we’ll be fast friends. So finally, we all make plans to go watch the school rugby team play one afternoon. I’m sitting there with a few other friends, and my friend comes around the corner with this guy I’m supposed to meet, and my immediate reaction is “Oh my god, I would hit that.” But being an awkward little fucker, I’m so bad at the getting-to-know you small talk that I so badly want to make with him, and I’m sitting in silence wracking my brain for an excuse to talk to him.

And that’s when I decide to ask him if he knew the rules to rugby. I laughed and said I wasn’t sure what was going on in the game, and would he be willing to explain it to me? My friend is giving me this “wtf” look, because I played rugby all through high school so I definitely knew the rules. But I couldn’t think of any other excuse to have an extended conversation with him, and I desperately wanted to. So I sat there like an idiot, pretending not to understand the sport I’d played for 5 years, just to have an excuse to chat.

Anyway, we’ve been together 11 years and just celebrated our 3rd wedding anniversary.

Also yes, I did eventually admit to him that I completely lied about the rugby thing.

35. In sixth grade, I called her, got her voicemail to her cell, and held my phone up to a speaker that was playing something.

You’re Beautiful by James Blunt.

The entire song.

It was… not subtle.

36. In high school, I learned tuba just to impress a girl cause she said she likes tubas.

Turns out she only said that cause she was currently dating a tubist.

37. IM conversation died down and couldn’t think of something to say so I spammed keys on the keyboard, hit enter, and said my cat ran across the keyboard. Oof.

38. Oh god I made a fake Facebook account to post on my wall and talk to him so it looked like I had made friends. I hate middle school me.

39. Leaned over in English class every day and copied his handwriting until ours matched. I had this theory that if our handwriting looked the same he would fall in love with me, but he turned out to be mean, and I wound up with pretty handwriting.

40. I would yell a lot and be extremely loud when around them. It didn’t work.

41. Back when I was in middle school I had a crush and this girl. I was into writing at the time so I put her in a fantasy story i wrote, where she was a warrior. She hated it and told everybody, and showed them the copy I gave her. This did not help my bullying. I still die from thinking about the cringe.

42. In elementary, I went to school with a couple dudes that were very gymnastically inclined. They would do a double backflip off the swings instead of just one. They would do flips off the monkey bars, standing back flips, wall flips, you name it.

The girls loved them, they would sit and be an audience for these guys every lunch almost.

I got jealous. I practiced on my trampoline for a few days, tried some hand springs (which I got pretty good at, forwards not backwards)

Then the next time they were showing off, I joined them. Boom guy #1 comes running through; hand spring, cartwheel, back flip, back flip. Guy #2 comes bolting behind him; cartwheel into ariel, into backflip.

Here I come, cartwheel, into back hand spring…. oh wait, I dont know how to do one backwards, land on my neck, wind myself, start crying.

43. I was 15 and I had a crush on this boy for two years. One day a friend of mine told me that he was about to ask me out. He came up to me, said hello and while anxiety took the best of me I wanted to look cool so I said: “Hm, do I actually know you? Are you new in school?” He instantly turned around and left. We had been classmates since elementary school…

44. Thirteen years old, I learned my crush had taken ballroom dancing lessons. Delighted to have something to talk to him about, I proceeded to harass him all of homecoming with what I probably thought was good-natured ribbing. Looking back, I was being an asshole and straight up making fun of him. Poor guy took it like a champ, but fucking hell I had no idea how to be social.

45. In 12th grade I had a huge crush on this guy in one of my classes. I knew his favorite book and movie was Fight Club, so I Googled everything about it (along with watching the movie). On Valentine’s Day, I sent him a card that said I want to have your abortion and gave him my phone number.

46. We had a foreign exchange student my Freshman year of High school.

She was French and absolutely gorgeous, so naturally, all of us boys were smitten with her. She was in choir and sang really well, so I figured since I was a musician as well, that was my “in” with her.

So, I busted my ass and learned a love song from a very popular French Opera. It took me a really long time to memorize and I thought it would be a bold gesture. So, I sang it to her flawlessly and asked her how she liked it, thinking that taking the effort to learn a love song in her language would be a great gesture.

Well.. That day, I found out that she was Swedish, not French. I’m fucking stupid.

47. Told her on AIM I had a crush on someone. When she asked “who?” I waited a bit then typed” you” and signed off dramatically.

We did not get married.

48. Called crush’s phone every 60 seconds for an hour (no answer, repeat). I figured she’d pick up once she got home and I wanted to talk to her ASAP. Unfortunately, she was on the phone with someone else the entire time, getting the “you have another call” notifications about incoming calls, just wasn’t responding to them. After about the 60th time she picked up and screamed WHAT!?!?!?!?! and I tried to worm out of it like it wasn’t me that had just called her over and over and over. She didn’t buy it of course. This one still keeps me up at night 30 years later.

49. I used to poledance on a lamppost outside a boys house when I was 13.

50. I asked her out by parking outside her house and writing it on the windows of my car in car chalk. She sent the dog outside and said “You should leave. My dog is outside he’s pretty mean.”