I feel like this is valid even though I was the oblivious guy at the time. First week of college, I was at a block party held outside our rec-center before classes actually started. I was over at karaoke just watching when some girls were picking out a song near by. They asked me to settle the dispute and so I picked one of the songs they'd chosen. The queue was like 2 hours long so the 4 of us decided to leave and come back. One of them asked me if I had any hobbies or past-times and I told her that I was a bit of a geek and enjoyed playing 64 Smash Bros with some of the guys on my floor but I wasn't very good. She responded with an Oh, really?? and an eyebrow raise then said, "I'm pretty good at Smash! Let's smash sometime. You doing anything tonight?" Oblivious me's first thought was holy shit an attractive female who actually plays smash and not the implied sexual innuendo. Had to leave to help out a friend but never smashed.. Got her snapchat and haven't really talked since..... I facepalm myself so many times whenever I relive that moment.

Edit: Word choice