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>when I was like 8, I had pretty crooked teeth. my English class used to have a penpal programme and I was assigned this extremely cute girl from Washington. one day she sent me a pic of her and asked for one of me, naturally my crooked teeth showed up noticeably so I wrote they were Halloween fake teeth
>when I was like 13, I had a crush on this Romanian girl, we were friends and all and everyone knew I liked her a lot (herself included). one summer night me, all my friends and here were hanging around and everyone was saying "just tell her" aloud, and she kept asking "saying what?". after a while I brought her to a secluded place, told her I liked her and she said "I have to think about it". I haven't received a reply to this day. this was 15 years ago
>4 years ago me and my gf went in Naples, we met and started chatting with this group of old ladies while waiting at the pizzeria. after dinner me and my gf were walking back to our hotel, when we casually found the ladies again and they offered us a ride. we accepted and when we reached our destination, I wanted to offer them some money for their kindness, but I just said "[gf name], can you give me my wallet?" aloud. I immediately realized how rude that sounded (I should've just told them "may I offer you something for your kindness/may I repay you for your disturb/whatever"). they kinda laughed it off but you could really tell they had second hand embarassement
these are the three cringiest moments in my life
there's another one, but it's nothing major
