So, when a Reddit user asked, 'What is the most embarrassing thing you've ever said to someone you were trying to impress?' people were ready to share.
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 which said 'Vienna Rocks' on it at the time. She thought I was joking. - Ok-Fudge8848
Was wrestling with a friend and we fell on and broke a Foosball table. My crush walked in the room and I said with a stupid smile, “I did that sh^%t.” She left without a word. - BurghFinsFan
Crush in HS worked at an ice cream store. When she asked for toppings I said “I’ll have Reese’s penises please.' The store laughed. - WhaleyWino235
I manscaped for you (in front of my whole HS Spanish class) - BalinAmmitai
'..so you study here ?' I said this when she was in front of her classroom. - phibii
I was getting to know a girl once. She said “I’m a librarian.' I said “I’m a Capricorn.' - Radiants_Table
Trying to lie about my age.
Her: 'You're too young, how old are you?'
Me: 'I..eh um..I'm like 20 or 21 I am.'
As the Sentence left my mouth I realised how ridiculous I had just sounded. - Sonnyboy1990
I once attempted to impress someone with my extensive knowledge of ancient civilizations, but accidentally referred to the Aztecs as the 'Avocados.' - Creative-Ad5487
I can do a Kickflip, then proceed to elegantly snap my ankle - Mrlightyboy
Was on an airplane years ago with my girlfriend and her parents. My girlfriend couldn't get a seat next to me and sat directly behind me. During the flight I thought I would surprise her and reached me hand back onto her knee. Slowly I kept extending it up her thigh until I heard giggling.
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. Was so embarrassed - Ladon1949
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 “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. -inexistences
Your eyes are like Mushroom. She laughed so hard that we dated for 7 years. - rcorum
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 which said 'Vienna Rocks' on it at the time. She thought I was joking. - Ok-Fudge8848
I told a musician I like that I liked a specific song. It was not his song. - Naca-7
Went to Warped Tour, they had a contest to submit a photo and the winner got to meet one of the bands. Took a sick shot with my blackberry, submitted it in its low resolution glory and won somehow.
Honestly had no idea who the band was, but I met them, got a signed poster, shook all their hands. Then I said “you guys were awesome, great show.' Singer said “well, we haven’t played yet so…” - PancakesandScotch
While on a semi date, said I was presbyterian when asked if I ate fish. He looked confused. I meant to say pescatarian. - Sea-Inside2677
I didn't say anything. When I get nervous, I tend to burp a tiny bit uncontrollably. I burped in my manager's face. - throwitawaybongybong
'If you had brains in your cheeks, you'd be smarter.' It was a compliment, in my head - Smegma_Surfer
I once called my potential interest “sturdy” and he was so offended. I tried walked it back by talking up how strong he was and how I could run full speed into him and he would budge. We’ve been together for almost 7 years now - he’s used to my stupid compliments and just smiles and pats my head in reassurance. - Awkwardpanda75
I was around 15, 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. - LGBecca