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We humans are quite funny creatures at times, and often find ourselves in awkward situations. Especially when it comes to relationships! Sadly for us, those memories that make us cringe will haunt us for the rest of our lives, but there's actually a way to survive - just laugh it out!

So, get your popcorn ready and let's share the worst fails you made in your first relationships!

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#1

The first time I kissed a guy I was 18 years old... Up until then my only exposure to kissing was from sex scenes in shows/movies. So when we started making out (in public... In the SUB at our Uni), I made moaning noises because I thought that's what you were supposed to do! God, I hate myself. I can't even look at him anymore... I just see idiot me moaning like an asshole Mmmm Mmmm mmm uhhh mmm whyyyyyyy?

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    #2

    Started kissing in a Target parking lot. She got on top of me and took her shirt off only to realize that the family in the car in front of us was watching

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    BunnyBlubber
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    #3

    Thought it would start like in the movies. She kissed me, pushed her onto the bed. Tried to take off her pants then her mom walks in.

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    Tayeb Smith
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    #4

    **FRESHMAN YEAR IN HIGHSCHOOL**My girlfriends birthday was coming up and I wanted to get her the perfect present. So, I asked my older sister to help. We go to the mall and I wanted to get her this gem-encrusted necklace but my sister told me that was too predictable. She said, "if I wanted to keep this girl, I had to be unique and appeal to her feminine side". So she leads me to the sex shop where she picks out this ridiculous looking thing called a rabbit. She said, "if I get her that it would make me seem confident and that she would think about me every time she used it". Both of those things sounded great to me so I bought it, I wrapped it discretely and I couldn't wait to give it to her. I made sure I caught her at her locker and I gave her the present. I told her not to open it here and to open it later. Hoping that she would just put it in her locker and open it when she got home. Lunchtime comes around and we are in the cafeteria. When I meet her at our table she is surrounded by her friends with a table full of cards and gifts and my terribly wrapped dildo was right smack in the middle. Before I could say anything, she grabs it, announces that "this one is from my boo" and opens it. Everyone just froze and of course, they then chime in with their "Oh my gosh's" and "what a freak?" " what kind of girl do you think she is?". Then she turns it on and puts it in the middle of the table vibrating and spinning and of course attracting more people. I was so embarrassed, I couldn't move. Needless to say, she didn't appreciate the gift as much as my sister said she would. We broke up not too long after that. I really hope she kept the toy and thinks about me when she uses it.

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    Alan Turns 9
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    Daniel Mallory
    Daniel Mallory
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    6 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    i actually laughed at the end also i think i heard this one before

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    #5

    My first girlfriend in high school, first time making out...on a balcony during a party. I thought in order to make a woman feel good, you had to squeeze the living hell out of her nipples. NO idea where I got that. Hurt so much she fell down and yelled at me.

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    Kurtz Frausun
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    #6

    In my first make out session I had no clue what to do, so I bit his tongue. Hard. He left shortly after.

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    Hazelnut
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    Barbara
    Barbara
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    6 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    Love hurts, but most times not like this! Hope you didn't 'Mike Tysoned' his tongue?

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    #7

    In my first relationship, I was on the playground after school with my boyfriend (we’re not together anymore).he was reaching over to kiss me, and I leaned back toget away from him and I fell off of the platform we were on. EMBARRASING!

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    Kawaii Panda
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    #8

    I leaned in to kiss my first bf. I missed and ended up with my lips in his nose. He laughed and kept me anyway. Still together to this day.

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    IWishIWasBob
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    #9

    When i was kissing with a girl i was with for about 4 months ....
    She sat on me and after a while of her wiggiling i got a boner.
    Awkward when you are 16 and she feels it....
    (We broke up 1 week later

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    Pull King
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    Lucida
    Lucida
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    6 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    Seriously, what's to be ashamed of? If I was sitting on a 16 year old boy, wiggling and kissing, and he would NOT get a boner, I would feel insulted.

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    #10

    16 - 17 years old : Being too exclusive, wanting to be just the two uf us all the time, thereby refusing to "share him" with his friends and not socializing enough. Also, thinking sex was the best thing I could do to show him my love, resulting in a relationship where all we did was sex. Needless to say, he got bored of it after a while and I had the worst heartache of my life because I was genuinely in love and just too stupid to open up to his world and his friends...

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    Linouchka 99
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    catmarshall57 avatar
    BusLady
    BusLady
    Community Member
    6 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    Maybe you took the relationship more seriously than he did. Sounds like you were hurting more from the breakup.

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    #11

    literally couldn't kiss properly, when i tried i hit my nose because i was moving too fast

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    Aidan Edwards
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    #12

    Late bloomer here.
    After we broke up, we still shared the same circle of friends. Ended up staying at the same hotel for an event. To make an embarrassing night short: Got drunk and thought it would be a good idea to knock on his door in the middle of the night. Very loudly. For about 15 minutes.
    After that I staggered back to my own room, cried under the shower, almost drowned myself because the alcohol made me drowsy (it was a nice hotel with a giant shower big enough to comfortably crouch in) and woke up the next morning with an epic headache and missing memories of the night before. Sadly, the cringy ones were still crystal clear.
    Best part? Met him and the others at breakfast. Pretended not to remember anything. It felt like the meal would never end.

    My silver lining: I never got this drunk again and the next time we met, he was extremely rude to some other girl so I got reminded of why breaking up with him wasn't entirely a sad thing.

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    Arietis
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    #13

    In college (yes, I was a late bloomer) I flew across Texas to visit my older brother. Brother introduces me to his friend, George. George asks me out on a date. We had a few beers and then went to the county fair, and I rode the "Zipper" for the first time. Got off, and threw up on George's shoes. About a month later George DRIVES eight hours to visit me at college. I was sick with tonsillitis, but he had driven all that way. He picks me up to go to a movie. I'm running a fever, and threw up in his car. Never made the movie. Never saw him again.

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    K. Guyton
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    #14

    When I tried to seduce him but I failed. I found out he's a gay.

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    maxee
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    #15

    well where to start aha well i was in a relationship with a boy called keenan and i was in year 5 at school my mum made us a picnic to have in the garden all was going well when i caught a glimpse of a pik axe in the garden i lifted it up thinking i could show off and didnt relise he was behind me and he got a pik axe in the knee and had to go to hospital then asked me to marry him WTF!!!

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    shannan cottrell
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    Anne Lanham
    Anne Lanham
    Community Member
    6 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    I used to be an adventurer like you, then I got a pick axe in the knee!

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    #16

    The Cringiest Thing I’ve Ever Done Is Nothing.
    *forever alone*
    *Insert Seinfeld Theme*

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    hyprstorm
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    Allayna
    Allayna
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    6 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    It's okay, me too, and I'm already in High School ( ,_.)

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    #17

    losing my virginity at 15 and having his brother walk in on us.

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    Minnie-me
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    Gayle Bynum Cardosa
    Gayle Bynum Cardosa
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    6 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    So far that wins as the cringiest and not in a good or funny way. Just sad.

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    #18

    When I was 12 I decided to ask this guy out. He said no, AAAAAAANNNNNNNDDDDDDDDDDd he told his mom that he found out I liked him. His mom said ¨I could have told you that at the start of 2nd grade. (Yes. I liked him for that long) Later that summer we were both volunteering at VBS together. He was in a group with my best friend. on the last day of VBS, he asked me out. Later that night he hugs me... his mom saw it. (she was standing at the window) Later that month he had surgery. I spammed his phone and blah blah blah. We were hanging out one day and my brother was fascinated with the scar on his chin (he had oral surgery... like me :)) so my brother touched it and asked if it hurt. he said no. then my little brother Kicked his face. and asked if that hurt. we broke up the next day

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    MADELINE ELIZABETH
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    #19

    My first boy friend and i 'got married' on our fist date and he dressed as the doctor from Doctor Who
    but it was cute and funny since we were little

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    Pasca Mouse
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    #20

    Well apparently its not sexy when to make your move in a "moving car" which leads to car crash!

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    Nini Meow
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    Barbara
    Barbara
    Community Member
    6 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    This honestly is the 'plot' of a commercial I've seen on TV :D

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    #21

    Once i was like,7, i had a relationship with a boy named Paul. I came to him and SPRAYED HIS FRICKIN FACE WITH WATER! And that is, my dear friends ,the story of how I , ended up being an introvert.

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    penguin sock
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    Ben Smith
    Ben Smith
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    6 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    You don't have relationships when you're 7. You have friends and you were goofing off, big deal.

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    #22

    So i was madly in love with this guy, (he liked me too) and all je did was trying to set me up with his friend/brother who was into me. So eventualy his friend gave up and he was starting to show interest in me. I was so nervous and worried coz i didn't know how to kiss, and i through he was experienced. I came up to idea to make a deal whit that friend of his. I was to kiss him (which he really wanted) to practice making out and he was supposed to keep that secret. We kissed, turns out i wasnt that bad. Later , i ended up with that guy i liked and almoust broke up coz his friend couldn't keep a secret. I did it all so i didnt embarrass my self i coz i thought i was wayyyyy out of his league.
    So that is the story of my first bf, but we are still together, its been 5 years ago.

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    Niko chan
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    #23

    I leaned in to kiss my first bf. I missed and ended up with my lips in his nose. He laughed and kept me anyway. Still together to this day.

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    IWishIWasBob
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    #24

    I bought a new pair of jeans for the first date and we were watching a movie when he asked "New jeans?" I said "No, why do you ask?"...so he reached over and pulled a long clear plastic size tape off the leg that I missed when getting ready. Busted!

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    Sphinx905
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    Shruti Naik
    Shruti Naik
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    6 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    This is sweet and innocent. Its ok! don't have to be embarrassed about it! In a few years, you'll laugh about it!

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    #25

    My first girlfriend is a long distance relationship and when we met im trying to do an effort. Its too hot in that day so i borrow her umbrella (she was holding) to cover her in a sunny day. We slightly debate because she want to hold it by herself but i win and when i trying to open it. I do my best to open it even my face express how hard im trying to open it. And when my girlfriend notice me acting weird. Its too late. I open the umbrella. It is a umbrella that you need to click to open it (it wasn't that trend at the time.) I ruined the umbrella and she gave me "i told you so" face at the same time

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    Charlyn02
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    #26

    Not me, but a friend. Almost went all the way during a sleepover- parents walked in. Oh God... He came to school the next day and proclaimed he would never have sex until he was 16.

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    Elizabeth Schuyler
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    #27

    When we started to date, I was having braces at that time. I was coming to meet his parents and he picked me up with his friends and immediately took us into restaurant so I could get something to eat. However, I was very shy about eating on public and in front of him (braces) and didn't really get the part that we were there because of me, so we spent there 30 mins until I said I don't want anything and they were all like "so why the f* are we here?!". And, well, I didn't meet his friends again.

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    Suzi
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    #28

    In the third grade I had a boyfriend that was born on the same day as me but 11 hours older. So I was ready to go to second base (holding hands) and worked up the courage. My friend (bp name Pet lover ❤️) told him to do it and he held my hand and freaked out running away to the playground smiling. We broke up in the beginning of fourth grade...

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    Furious_Lover
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    #29

    I met him at the library when i was 12. We hit it off and after a week he took me home to meet his mom. I freaked out when i saw his posters and kissed them. i never kissed him.

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    Emily Eve
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    #30

    Oh lord.. You're making me remember this again. Ok so this was when i was in 5th grade (the grade where you turn 11 years old) , and i was the (wannabe) "popular" kid.. I had to date people to keep my popularity up because there was other people that kept bringing down my rank. So i asked random guys out and one of them said yes.. That took my popularity level way high up because he wasn't the best looking guy. After 2 days a dumped him. Man i was a stupid child.

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    nosoul
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    weatherwitch101 avatar
    weatherwitch
    weatherwitch
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    6 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    I find this one so disturbing. Dating at 11 AND it's a popularity contest that affects your rank?! At 11? Dating is about having fun, getting to know someone, enjoying life it's not a contest 😒

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    #31

    This wasn't exactly a relationship but it's still the most humiliating moment of my life and probably Is for him too. I was friends with some dude in a club in high school, already in a relationship myself. He had a three year girlfriend and I was really under the impression we were 'bros' (I'm a girl, not a dude, but I think women can be Bros). He invited me over to his house to work on a project, told me his family was home (they were. Mainly his older sister and a sibling). I was 17 and disgustingly immature so I brought a bottle of whiskey. Wanted to be cool and all that. Long story short I drank half the bottle (never drank before in my life), and he drank one sip. Ended up doing questionable things he asked me to do, don't recall a lot. Not proud of it. The weird part is his sister freaked out on him HARD afterwards. Made us go to the mall and get me pizza after I could stand up straight. He's still with his gf as far as I know. My reputation went to zero and I moved out of state. still hate myself for it. I did tell my bf at the time and we broke it off, mutually. Most horrible thing I've done to a guy. I didn't deserve him.

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    Okiedokie
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    Kahlo Smith
    Kahlo Smith
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    6 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    That creep took advantage of you. I'm sure it was hard for your bf too, but that wasn't something horrible you did to him, it was something horrible that guy did to you-- and I'm sorry you had to go through it. I'm glad that his sister tried to defend you, good for her, and good for you for being able to make a new start-- but you shouldn't hate yourself for something you did not have control over.

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    #32

    My first boyfriend and I are good friends to this day, but our relationship (which lasted about a month over the summer of sixth grade) was a joke.

    Probably the cringiest thing I did was break up with him after a month because some kid at camp had a crush on me and I decided I wasn't into my boyfriend anymore, mainly because it was summer and I wasn't spending as much time with him. The kid and I never got together, it just made me rethink my commitment.

    Ah, the folly of young love! Today, I'm in a happy long-term relationship, and he's openly gay, so I'm glad it didn't work out.

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    Kahlo <3
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    #33

    Not really relationships but so cringe. First, I liked one boy in middle school but never even talked to him... Instead I kept what I called “the Devin Diary,” a detailed account of anything I saw him doing or heard about him that day. I wrote fan fiction and poetry about him too.
    Another one, first time my feelings were returned by a boy, I made an online account dedicated solely to shipping us. So embarrassing when I look back on it, but he was okay with it and it’s still up

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    Chancery
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    #34

    Not having a first relationship....

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    #35

    "I love you" - first boyfriend
    "uh.... you too" - me

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    Courtney Graham
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    #36

    I dated a guy when I was 14 for about 2 months. We texted all evening most days, but in person we were super awkward around each other. He was always more focused on his best friend, and wouldn't go beyond hugging and hand holding with me. We went on a field trip and got into a fight because I felt like he didn't care, and he gave his phone to his friend to fight for him! Then the next day (it was an overnight trip) of course everyone knew about it, and his girl friend (she was kind of a pretentious b*tch) basically forced us to ait down and talk about it (neither of us wanted to be there). It was super awkward, and she mediated the whole thing. It ended with a very awkward hug and me running off to my friends almost in tears. We broke up about 2-3 weeks after that. He's currently dating a crazy chick who got so jealous of our later friendship that she virtually wouldn't let me be near him, insisting that I was in love with him (not even close). That girl unfortunately ended our friendship.

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    Kyra Lindsey
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    #37

    I let my boyfriend mentally abuse me because when he was at my place I was safe from my sexually abusive dad. I was 15. I now regret not leaving him and moving to my mom.

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    Gnomenn
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    #38

    During my first relationship, some creepy guy told everyone I was his girlfriend. I just played along. I pretended to love him. The creep believed it...until he caught me kissing my real boyfriend...

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    user
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    #39

    I was freaking out because I was 15 and hadn't been kissed yet so I decided to ask my best friend to make out with me and it was the worst decision ever. He agreed, took me to the basement of the school, and I kissed him FULL TOUNGE and it was so gross. Like so gross. He's gay now.

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    Katie Linder
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    #40

    The Cringiest Thing I’ve Ever Done Is Nothing.
    *forever alone*
    *Insert Seinfeld Theme*

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    hyprstorm
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    #41

    Well my first relationship is my only relationship :) So blessed that my first boyfriend ended up being "the one". We're married now. Anyways, when we were about a year into our relationship, we went on a short trip together and stayed at a bed and breakfast. I made it clear from day one that we were gonna stay virgins until marriage (yes, kind of out of the norm, but I'm old-school like that). Well things got pretty heated up one night on the trip. He then asked me if I wanted to have actual sex. I said "no, no!" like I was all surprised and upset. We stopped fooling around for the night and went to sleep and it was very awkward. Kinda my fault for leading him on that night. I told him from day one we were gonna wait until marriage, but he thought I changed my mind. Yeesh it was awkward. Lol but everything worked out for us and I knew it would.

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    Bored Office Girl
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    #42

    i told him i liked him...
    via an email to the address he rarely checks
    we're still dating tho nearly a year later

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    trinity davis
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    #43

    I was 16 and my boyfriend and I were making out pretty heavy on my bed and I had my shirt and bra off ( no sex) but my older brother walks in as my boyfriend is busy with that, and the look on his face was horror. I was mortified, my boyfriend froze and my brother just shut the door, nothing was said and it lasted only maybe 5 sec. It's a memory I will unfortunately always remember.😣

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    Jennifer Walker
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    #44

    I am best friends with the guy I like so when he was dating someone
    I looked mad but I wasn’t so he asked do you hate me Then he was like never mind I don’t care if you do anymore because I’m not desperate.So I said for friends he said no for a girlfriend cause I actually liked you.Then the day after Valentine’s Day he broke up with his girlfriend.Fast forward to today we are closer than ever he almost my nose when we were playing a game,when it’s wet we fell and we were soaking wet.Okay he made a joke and told me it was about me then he was like just kidding I love you grill.Meanwhile the math teacher was behind us the whole time after he was pretending to motorboat himself.So we all cringed

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    Mc’scuse me
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    Stef Bollen
    Stef Bollen
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    6 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

    The math teacher tried to motorboat himself? :D I don't really understand what happened in the last 5 lines

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    #45

    When I was 12 I decided to ask this guy out. He said no, AAAAAAANNNNNNNDDDDDDDDDDd he told his mom that he found out I liked him. His mom said ¨I could have told you that at the start of 2nd grade. (Yes. I liked him for that long) Later that summer we were both volunteering at VBS together. He was in a group with my best friend. on the last day of VBS, he asked me out. Later that night he hugs me... his mom saw it. (she was standing at the window) Later that month he had surgery. I spammed his phone and blah blah blah. We were hanging out one day and my brother was fascinated with the scar on his chin (he had oral surgery... like me :)) so my brother touched it and asked if it hurt. he said no. then my little brother Kicked his face. and asked if that hurt. we broke up the next day

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    MADELINE ELIZABETH
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    #46

    Enduring blowjobs where he used his teeth to gnaw at my dick because his jaw was wired tight.

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    Final score:
    -4points
    Trevor Stripling
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