People Are Sharing The Humiliating Yet Hilarious Moments They Tried To Impress Someone And Failed Miserably, And The Secondhand Embarrassment Is Toooo Real
Reddit user u/Klutzy-Hippo402 posed the question: "What is the most embarrassing thing you've ever said to someone you were trying to impress?" The thread quickly filled with hundreds of hilarious stories of people admitting the stupidest things they've said and done to try and look cool. Here are some of the most hysterical:
1."In sixth grade, I took my first-ever girlfriend to the movies. I wanted to hold her hand, but I was terrified and wasn’t sure what to do. I started giving her a sales pitch on how awesome my hands were. 'They’re really good at holding stuff, like boxes…or jugs.' I was truly thinking of milk jugs (god knows why), but accidentally suggested I could just hold her boobs. It’s been more than 20 years, and I still think of it regularly."
2."I was on an airplane years ago with my girlfriend and her parents. My girlfriend couldn't get a seat next to me, so she sat directly behind me. During the flight, I thought I would surprise her, so I reached my hand back onto her knee. Slowly, I kept extending it up her thigh until I heard giggling. I looked behind through the seats and saw that my hand was on the leg of the guy next to her. He saw my face and said, 'I just wanted to see how far you'd go.' Of course, my girlfriend was in on it and started laughing along with the rest of the row. I was so embarrassed."
3."My university boyfriend invited me to meet his friends at a house party. His friends were known to be quite judgmental and historically not nice to their friends’ girlfriends. I was so nervous in the car on the way over, so my boyfriend kept telling me to just try and spend some time with a guy called Johan (the nicest one of the bunch). As we pulled up, one of the friends came out to the car and my boyfriend said, 'That’s Johan. Talk to him.' I got out, extended my hand, and said, 'Hi, I’m Johan.' There was no way to recover from that."
4."When I was first dating my now-wife, I set fire to the restaurant and some random guy at the table next to me put it out. I bought him a drink to say thanks and spilled it on his date. I wanted to die."
5."One day, I went to my boss's chamber and saw his arm in a cast. I wanted to say something sympathetic and score some brownie points, but what I said was, 'Sir, your arm is broken.' He looked at me and said, 'I know.'"
6."My crush in high school worked at an ice cream store. When she asked what toppings I wanted, I said, 'I’ll have Reese’s penises, please.' The whole store laughed."
7."I went to Warped Tour, and they had a contest where you submitted a photo and the winner got to meet one of the bands. I took a sick shot with my Blackberry, submitted it in its low-resolution glory, and won somehow. Honestly, I had no idea who the band was, but I met them, got a signed poster, and shook all their hands. Then, I said, 'You guys were awesome. Great show.' The singer said, 'Well, we haven’t played yet, so…'"
8."I said, 'Your eyes are like mushrooms. She laughed so hard that we dated for seven years."
9."I did once (truthfully) tell a girl from Austria that I didn't know what the capital of Austria was, which wouldn't be too embarrassing, except that I was wearing a T-shirt that said 'Vienna Rocks' on it at the time. She thought I was joking."
10."I kissed a girl for the first time when I was 13, and something prompted me to say, 'Average.' She loathed me for the rest of the academic year. Cut to six years later: I matched with her on Bumble. We met, we had sex, and she looked me dead in the eye and said, 'Average.' She is my best friend now."
11."I told a musician I like that I liked a specific song. It was not his song."
12."While on a date, I said I was presbyterian when asked if I ate fish. He looked confused. I meant to say pescatarian."
13."I was trying to make a good impression on my ex's god-sister (they were very close), and in my anxious state, said, 'I used to have butt hair,' rather than, 'I used to have butt-length hair.' Yeah, that didn't earn me much favor."
14."She said she was going to the botanical garden over the weekend, so I told her about the time when I was 3 and got kicked out for eating the plants there."
15."When my dad was a kid, he tried to impress an older lady. She had asked him what he was studying, and he confidently told her he was studying Latin. She seemed really impressed by this, so she asked him to speak a bit of Latin to her. He knew one word, and created a bunch of other words around it that sounded Latin-ish. She frowned and told him it was a bad thing to lie. Her job? Latin teacher."
16."I once attempted to impress someone with my extensive knowledge of ancient civilizations, but accidentally referred to the Aztecs as the 'Avocados.'"
17."I was laying it onto this beautiful lady at an outdoor concert. I was all smooth and suave, talking like I was a big shot and like I knew all the right people there. So, I thought it'd be a good idea to drop the name of this semi-famous lead singer from a local band I supposedly knew. You know, I wanted to show her I was connected and all that. But, the problem was, I screwed up the name entirely. Turns out the person was a relative of hers. She started asking questions. Her eyes got wide, and she started laughing so hard, I thought she was gonna pee herself. I felt like my face was on fire. I knew I couldn't salvage the situation, so I just laughed it off too and admitted I had no idea what I was talking about. We ended up talking for a bit, and we actually had a good time. Learned my lesson, though. Never try to inflate your reputation with nonsense. It can backfire real quick."
18."One time, I sat outside at a hipster coffee shop in Santa Cruz and pretended like I was composing music. I wrote random notes on a page and I would periodically look up with a strained look while waving my pencil like a tortured conductor, pages strewn across the table. Thank god nobody approached me that could actually read music. I can't read music."
19."I was trying to impress a girl among a group of girls and a spittle from my mouth hit her in the eye. Needless to say, I left quietly, leaving behind a hullabaloo."
20."Met a girl and went to dinner at a cafe. During the conversation, a bet arose, and I said that I could eat everything on the menu of the establishment. Half an hour later, I destroyed the toilet, and she successfully escaped. But, I won the bet."
21."I was walking to the garage to get my car. I was wearing a very tight skirt just above the knee. I came across this guy, and we flirted. On my way to the car, there was a little step down, and I didn’t see it. I placed my foot exactly on it, so I needed to make a big step to correct it and pick up my balance. I couldn’t with my tight skirt, so instead I did a couple of small steps and fell to the ground. SHAME!!!!!! Now I can laugh about it, but I must have looked really stupid."
22."I tumbled down a flight of stairs when trying to 'parkour' my way to a group of cute girls in ninth grade."
23.Finally: "I was around 15 and going through the receiving line at my cousin's wedding. This was my first 'grown up' wedding and I wanted to act it. As I hugged my cousin, I blurted out, 'I'm so excited to be here! The last wedding I was at was your first one!' That has echoed in my head for 30 years. This was my cousin's second wedding, the groom's first."
Have you ever said or done something super embarrassing while trying to impress someone? Tell us in the comments!
Note: Submissions have been edited for length and/or clarity.
