I "went out" with a guy in high school - meaning he asked and I said yes on Friday, avoided all communication for the weekend, and then quickly ended it on Monday. I was shy and scared and awkward and chubby, but this kid was also...odd. Think like southern hick but living in the northeast US in a relatively affluent neighborhood. It was just...uncomfortable all over and I was not into him. Lots of other girls felt ick about him.
Well it was a cringey memory until my senior year of high school (he was in my grade) when my sister became a freshman. The kid was in our friend group so he got invited to hang out a bit and he ended up asking her out too. She strung him along much longer, applying the same tactic as me - avoidance and ignoring. And yet he insisted that they were still dating even after more than a month of zero contact. It was just all over so cringey.
Anywho, it's all been a distant cringe (especially since my dad loved to nag us that we both had the same first boyfriend and he was a weirdo), but recently it's turned hilarious. Come to find out that he had asked out several of our girl friends throughout high school as well, all ended similarly of him not catching the glaring hints that these girls wanted nothing to do with him, and having a rebound time of about .2 seconds. Well, he began messaging us all on facebook, telling us all the same thing, about how we "ruined other girls" for him.
I could almost give him the benefit of the doubt as a desperate kid if he didn't think us girls would talk to each other, but he sent the same messages to my sister and I. We live in the same house. We're sisters. How would he not think we'd talk???
Anywho, now I look back and laugh but inside my whole body cringes that I "dated" him in high school terms, didn't warn my sister, and actually continued to hang out with and indulge him for several years thinking that maybe he was just awkward and needed a friend and somebody to push him in the correct direction. Nope, apparently after being clear that I wasn't interested, he still "jokes" about how eventually I'll dump my boyfriend of several years and come back to him. Just cringing thinking about how long I have him the benefit of the doubt :S