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!

#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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    #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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    #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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    #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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    #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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    Barbara
    Community Member
    7 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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    #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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    #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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    Lucida
    Community Member
    7 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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    BusLady
    Community Member
    7 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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    #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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    #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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    #14

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

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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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    Anne Lanham
    Community Member
    7 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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    #17

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

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    Gayle Bynum Cardosa
    Community Member
    7 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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    #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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    #20

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

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    Barbara
    Community Member
    7 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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