What has been your most awkward moment in life?

Got creeped on today, so it made me wonder about your experiences.

What has been your most awkward moment in life?


3|2
28|22

Most Helpful Guy

  • My first ever time asking out the girl I had a major crush on ended up with me shouting "can I have your number?" across the school square in front of dozens of people and seeing her continuing to walk away. Everybody saw that rejection/me being socially retarded. Awkward!

    1|1
    0|0
    • Awwww, Dylan. You're so sweet, hah. Her loss.

    • Show All
    • You're welcome. 😊

    • Oh that's cool, incidents like these built up confidence, like if you can ask for a girl's number in front of hundreds of people and get rejected, you can easily ask out a girl in private

Most Helpful Girl

  • Not realizing that my boyfriend and I had broken up... lol. The worst part, I had just watched the Parks and Rec episode with Ann and Chris. Talk about awkward and you have it right there.

    2|0
    0|0
    • Awww, man, hah. That's rough. I'm sorry to hear that.

    • Show All
    • Thanks for MH! :)

What Guys Said 21

  • I'm thinking of back in middle school.

    I had a small crush on a girl. It was more like interested rather than full out crush. It was April fools day, but I didn't really register with that date in my head.

    I got to school and walked in. As I'm walking to homeroom, this girl I'm interested in says quickly to a friend of hers "OMG it's April fools day! *runs to first person she sees- me* Haha Randall I love you!" *runs back to her friends*" I was super super awkward in middle school and blushed a ton but poker-faced and continued my day.

    Later on, this girl was telling her friends what she did for April fools day. I overheard so I blushed a little (I was super awkward like I said). Someone saw and said "Hey look! He's blushing!" Then someone else yelled, "he must be crushing on her since he is blushing!" The whole class laughed and made their little jokes. She kind of was like "omg I'm totally not interested in that guy." The teacher smiled, let out a bit of a chuckle and watched it go on. I'm sitting there SUPER awkward. I reach down in my desk to act like I'm getting books since I can't deal with the gaze of everyone.

    I was only mildly interested in her, and tbh I would have blushed at anyone doing a joke like that at me. I was awkward like that.

    So yeah... I got pranked by mild crush, made fun of by the entire class, and then rejected by the mild crush. All because I blush easily 😑
    People teased me about it for quite some days after that.

    1|0
    0|0
    • You're so cute, Randall. 😁 Middle school sucks big time, though.

    • Show All
    • Mwahahaha. I'll keep that in mind.

    • 😱😱😱

  • meh I feel like there's been way too many to pick a favourite overall, I'll just tell you my favourite recent one. Was at a lesbian club party (long story) and I was dancing with my friends. They had glowsticks and I had placed one on the button of my shirt over my chest and swung it around like it was boobs for laughs... I was pretty drunk, no judging please. Then this super butchy 60 something lady came up to me, said "that's not where it goes", took it off, and placed it on the zipper of my pants, yes she felt "it". I basically got molested by a 60 something year old butchy lesbo, fun times.

    1|0
    0|0
    • Lmao, really? You sure she wasn't bi?

    • pretty sure, she wasn't, way too butchy to be bi. The funny thing is the very next day my friends and I went to this other club and as I was walking back from the bathroom someone grabbed my ass and I don't meant a small pinch, I mean got real deep in there and a real handful. At first I was like fucking "x" thinking it was my guy friend fucking around with me, when I turned around to my surprise it was a really drunk girl and she was fairly hot. She then screamed "wooooooo" (yes she was a wooo girl), grabbed my face and tried to pull me in for a makeout session. I grabbed her by the shoulders and was like "no, no, no, I have a girlfriend, no". She then said "wooooooooo!! I don't care, come here" and tried to pull my face in again for a kiss (she smudged my glasses, so annoying). So I asked her who she came with. She said with her friends. I asked her where they were and she replied with somewhere over there (while pointing), so I told her she should go find them hahahaha 😂😂😂😂.

    • Lmfao, "woo girls." Love that term.

  • Ran to the store to go pick up a couple of things...10 mins...11 tops... it began to rain on my way back, just for me come back and see that my parking spot which is in front of my apartment had been taken... we have assigned parking spaces :( . I had to go park in the guest area which is across the parking lot... and walk back... in the rain

    1|0
    0|0
    • Ohhh, I hate when someone takes my assigned space.

    • Show All
    • I've done the waiting around, too, on multiple occasions. 😒

    • hated having to go check like every few mins to see if they had moved. i was cooking too and i hate being interrupted when i do that.

  • Creeped on how?

    Well I've had a few I think but the one that first comes to mind is my dad walking into my bedroom once without knocking or anything while I was about to masturbate lol. I hadn't started to do it but I was naked. He made it even worse by not leaving right away either! I don't know if he enjoyed making me uncomfortable or what?

    1|1
    0|0
    • Two guys basically had a full blown conversation about my looks and getting younger women right in front of me.

      Hah, he got some sick pleasure from making you feel awkward, for sure.

  • When I was in 7th grade I went rollerskating with my girlfriend and a bunch of people. I was wearing cordoroy pants and while skating I became aroused and had a raging boner. Everyone noticed of course including the chaperone "who just happened to be my girlfriend's father". Fortunately he was totally cool about it and quickly escorted me off the floor and said hey let's go get a drink. So yeah how completely embarrassing!

    1|0
    0|0
  • Probably fucking up my 2 year long college grades, failing the family, myself and looking stupid in front of my friends... who now I don't even consider my friends anymore.

    In the end however, why should I care. Life is for enjoyment, doing what you want and for happiness.

    2|0
    0|0
  • 2|0
    0|0
  • Awkward? nothing really, others are the ones who make it awkward. Natural selection should have gotten rid of those people long ago

    1|0
    0|0
  • When I was 12 years old, a group of 18 year old women approached me at a park, and told me I was hot. They continued to stalk me around the park and I overheard one of those women say that she wanted to get naughty with me. I got to where my parents were and they stopped stalking me.

    1|0
    0|0
  • Hard to say but one of them was when I was at a party in college and saw the last three girls I hooked up at the time with talking to each other and standing a few feet away from me.

    1|0
    0|0
  • getting drunk, waking up to a girl, having sex for a record short time of 30 seconds , then throwing up again lol.

    1|0
    0|0
  • My life as a whole

    1|0
    0|0
  • A psychotic girl followed me after school... she still sends me friend requests after all these years

    1|0
    0|0
    • What is your story?

    • Show All
    • Ahh, the creepy messages do show up, too. Always entertaining.

    • haha I always wonder what they are like

  • When I was little I was at the playground and I spotted these group of girls, I went over to them and I must have said something insanely inappropriate, they beat me up.

    1|0
    0|0
  • you got creeped on today? doing it everyday you just don't notice lmao

    1|0
    0|0
  • Sister walked in on me and my ex right after we finished having sex
    Saw her frome waist up naked in my bed and she saw me standing there in all my glory
    "Awkward" is just the tip of the iceberg lol it was terrible

    1|0
    0|0
  • three stages of my life.

    1. Birth
    2. the most awkward moment
    3. death

    1|0
    0|0
  • What happened?

    1|0
    0|0
    • Two dudes being weird and having a conversation about me like I wasn't there basically.

    • Lol! Yaah, that can be very creepy.. glad your ok tho!

      Did i mention you that you are very pretty and i read all your opinions? Im like a good hearted stalker :) haha

      Most embarrasing for me? Mm damn i think it goes back to elementary school.. had to recite some poem and i forgot everything! Was a nightmare

    • Yeah, I'm fine. It was just awkward. Hah, thank you very much.

      Ah, yes, I did terrible in front of an audience as well.

  • Well almost everytime I try talking to hot chick and get nervous af

    1|0
    0|0
  • being in a mixed shower with older people

    1|0
    0|0
  • Being seen homeless. And having used old TracFones while everyone else had smartphones, lol.

    0|0
    0|0
    • At least you had a way to communicate in case of an emergency, but that is tough, for sure.

What Girls Said 27

  • Well we've all heard about the guy who wanted to put me in his pleasure prison who thought I had a swan neck and dove skin. Oh and a ripe body like a plum.

    *cough*

    2|0
    0|0
  • Too many to count. The time the guy walked up to me and said "You're so exotic and gorgeous" And proceeded to give me compliments and guess my ethnicity. Then after a good minute or two and him asking my name and stuff I say "I have a boyfriend" and his whole face drops and he's like "Oh I didn't" and basically runs away!

    It was so awkward.

    1|0
    0|0
  • I'd expect a thousand guys creep on you and you wouldn't even know they did Moolady! 😳 haha

    Something awkward happened when I was getting a sugar cane drink on Friday. The European guy was flirty. He looked at me up and down and said "you're quite tall o. O how tall are you?" I said "5'8" he then looked at my shoes and looked at me and said "oh nice" *winks*

    Freaking awkward as! I wanted to hide

    1|0
    0|0
    • I just liked your shoes :'(

    • Show All
    • Thank you, Moolady. <3 Always there for me! Hah.

    • Of course my love ❤️

  • I can't think of any at this moment!

    1|0
    0|0
  • We were talking about our boss's son and how lazy and hope less we think he is. When our boss peeked into the break room and asked to speak to the teacher who taught hin regularly and who was in the middle of a sentence when she came. God it felt like being sent to the p

    1|0
    0|0
  • Probably when I was walking down the hall at work. I was about to pass a guy I work with. Another guy called my name. I turned and flung my arm. Then I accidentally hit the guy in the crotch. He went down and grabbed his nuts. He was really good about it. But after that I got the nickname BB... ballbuster.

    1|0
    0|0
  • My entire life has been an awkward moment but I guess most recently was when creepy door guy at work asked for my number, lol.

    1|0
    0|0
  • My life is an awkward moment lol. One of many I can recall is when I was sitting in class talking to one of my crush's friends, who was sitting across from me. My crush came and walked over & they started playing fighting, then my crush got hit in the groin super hard and it hurt him because he held onto it in pain and just made eye contact with me for a long period of time and yeah I hated that

    1|1
    0|0
  • I know a guy from school who convinced me to discuss a tv show we are both into. I assumed we would do it over text, turns out he wanted me to go to his house and discuss it with him. Alone. I ended that relationship quickly.

    1|1
    0|0
  • When I was 16 some older guy tried hitting on me. In front of his young son too. Yuck :/ Not to mention my family was like 3 feet away.

    Then there was this time when some guy tried getting my number. Nothing wrong with that. But right before he approached me I overheard him telling his friend he recently got out on parole. Yeah...

    1|0
    0|0
  • Telling my crush I liked him, him saying
    "OMG you're so pretty but...*insert reasons* so no"

    2|0
    0|0
  • My life is full of awkward moments. But I hate when it's silent in the class and you forget to put your phone on silent and it rings and the whole class looks at you.😓😳

    1|0
    0|0
  • My life has been a series of awkward moments lol

    2|0
    0|0
  • So there I was, balls deep in a leprechauns ass... he tried to give me a reach around like I'm some kind of faggot. Totally fucked up the moment 🙄🙄🙄

    1|0
    0|0
  • Every waking moment of mine is pretty awkward. :-( its kinda sad...

    But i dont let that drag me down

    1|0
    0|0
  • Mine are too dark to be posted on GAG & something I prefer to forget.

    1|0
    0|0
  • There have been too many.

    1|0
    0|0
  • I'm just an awkward mess, let's be real.

    1|0
    0|0
  • I was changing dress in bathroom, i forgot to lock the door and my cousin entered the bath room

    1|0
    0|0
  • My life is one awkward moment

    1|0
    0|0
  • A few years ago I was wondering if you could see my pubes from the back of my body. So I took a picture of my butt and sure enough you could see the hairy bush that was between my legs. I forgot to delete the photo and then went to the Apple Store that summer. Long story short, the photo was seen by both my mom & a 50 year old man. I'd never been more humiliated in my life.

    2|0
    0|0
  • So far, nothing has been more awkward in my life than this.

    Seven years ago, I was an awkward, chubby girl who had a crush on a chubby guy. We both were made fun of for our weight, but what impressed me was that "hamburger" and all the names that they came up for him never seemed to affect him, and he would actually treat me like a person.
    We happened to be in the same gym class. One day, I was chosen to be team captain. And guess who I chose to be on my team first? Yup, you guessed it... the guy that I just so happened to have a crush on.
    Everyone burst into laughter. People were saying shit like, "Ooh, she likes him!" And then one of his close buddies put me on the spot. He said, "Do you actually like him, though?"
    Because I was so embarrassed and felt like my chances were over, I said no. And then I made him cry. I never felt so bad...

    That was in 7th grade. Seven years later, I go to one of friend's parties, and his little sister is there. (She's like, 15, and I'm now 18.) I'm super pregnant and just broke up with his father. She starts asking about crushes and love. This, was the most awkward talk ever, cause as I was talking to her, I was thinking, "oh man, she's gonna say all of this shit to him... ugh. Not again."

    My 7th grade crush refused to talk to me, even to this day. But hey, I don't blame him...

    1|0
    0|0
  • I had a panic attack in the middle of sex last night. So embarrassing.

    1|0
    0|0
  • My crush finding out I was crying

    1|0
    0|0
  • I went to the local grocery store to buy tampons, etc and this guy I went to school with who has and not being mean mental issues he was bagging the groceries at the store, he very firmly and aggressively smashed them all while staring at me said my name you look good today. My skin kept off my body in shock and horror. He stalked me at work for years, I did hair and even had to run him off several times by law enforcement. Yea he came up to me about 4 months ago in the same store. I wasn't happy. He said you're looking good, yea thanks but he's got mental problems so I can't be mean and tell him to go pound salt so I try my best to run the other direction if I see him

    1|0
    0|0
    • Oh, no... the stalkers are real.

    • Show All
    • That's good! I hope he eventually stops contacting you all together.

    • Yea me too, while I was pregnant with my toddler we went to the local Mexican restaurant and there he was! He looked at my husband and the look of pure anger was on his face. My husband laughed thought it was funny but I didn't. I was really pregnantly huge at the time. Scary for sure.

  • My most awkward moment and the first that came to mind was in high school. We were in building 2 which was the arts building and my crush and I were walking together to his class. We made it to the double doors and being the gentlemen that he is he had the door open for me. We were arguing back and forth about who should go in first he kept saying ladies first, joking about girls and chivalry these days, nice guys can't be nice anymore and things along those lines lol. In the end he grabbed me lol and pulled me into the door with him and we both kinda stumbled into each others arms. Kinda locked into each others eyes his hands really near my butt and then things got awkward. Lol I blushed and we continued walking to class I was smiling like an idiot the whole day.

    1|0
    0|0
    • Such an adorably awkward moment, though!

    • Show All
    • na she was really embarrassed because of it. Her freinds were even teasing her about getting what she deserved because of accepting. the guys also teased me about things going that way because I was acted in a gentlemanly way. We did talk we just never got together.

    • @Dim_121 oh well I can relate I never got together with my crush either 😔

  • When I stared some guy down for absolutely no reason. Still baffles me why I did that

    1|0
    0|0
Loading...