Most Awkward dating moments

What is your most akward moment while on a date? Let the cringe begin!

One time, this one girl took me antiquing. And it sounded pretty cool, so I was all in, because I love history and stuff. The first few places were pretty much a snore fest, but this last place? As soon as I stepped through the door, this strange pervasive energy washed over me, and left me frozen in my tracks. While I was trying to figure out what it was, I noticed the owner's dog who came out to greet me. I of course was all excited because it was a doggo, and I love animals, so I stuck my hand out in the universal greeting. Careful not to move too swiftly to startle it. But the dog froze, glanced up at me, then barked twice and whimpered as it ran off. The owner or the shop appeared dumbfounded. I was perplexed as well. Animals usually love me. "Why, he's never done that before!" She said, and my date looked kind of freaked out by this as well. Like 'Oh crap, what if I went out with a serial killer.' I of course tried to laugh it off and crack a joke, but there was still that awkward tension in the air. Then I finally honed in on the energy I was feeling and found a mirror where I noticed a lady in 1960s attire standing just to my left, where of course in the physical world, no one stood. I tried pointing it out nonchalantly (Cause this kind of stuff is fairly normal to me) but the antique owner didn't see it. Thankfully my date did! Because she shrieked and ran out to the car. I apologized for the awkwardness, then left to chase after her and hopefully calm her down. This is why I don't date people who identify as skeptics. Sooner or later, this kind of shit happens, and they never know how to handle it. Remember. Agnosticism is much more healthy of a mindset than either blind belief or skepticism. Leave the mysteries to due process. XD

My entire college dating history was cringe. There was one guy I met up with who said I looked nothing like my pics. (I wasn't wearing makeup.) The thing is, neither did he. He sent a pic of a guy with longer hair and piercings but showed up looking like he had been busting cattle on the range (aka like my dad.) We laughed it off a bit then I said he wasn't my type and too bad my friend didn't go to the same school because she might be into him. He asked for her number and I was like "haha, bye". Then there was another guy who I had a pity date with because I thought he needed some encouragement. During the date he proceeded to tell me how much he enjoyed sex with pregnant women, which in highschool and college the thought of pregnancy revolted me. Pity solved. Also who TF does that on a first date? These are a couple examples. This was when online dating just started and everyone had a fever. You weren't too selective and you met as many people as possible looking for "the one". Ultimately I stopped online dating in the middle of college. I started redirecting my effort to meet friends rather than dates. Was far better off. Plus one of them turned out to be dating material so we saw each other until he left for grad school, maybe a semester and a half. After, I just focused on graduating. Had enough crazies dates to last a lifetime. I thought I had an open mind but now I see I just had no concept of standards.

Oh here's another jewel for shits and giggles. I had dated a guy who had just moved back from Florida. Apparently he got mixed into some swingers groups while he was down there. Not only did he swing, but he also some how started seeing Mary Poppins from Disney World who also happened to be a swinger. So if you went to Disney World in the 00s and had interaction with Mary Poppins, I've seen her in several compromising positions (literally on the positions).

@sanfi

Heres another. So being down in Athens, Oh and living in Lancaster for so many years, I get used to just going to places on foot. Probably the only time I've ever met someone offline from this site was when I went to a japanese style arcade in Columbus which was really cool. Think like how an anime con sets up its gaming room, that was the vibe and set up of this place. But we eventually got hungry and decided to walk to a nearby Donotos on high street in Columbus. This was before Covid, so it wasn't as bad as it is now, but Columbus at the time had a rather high homeless epidemic, and they love to hang out on High Street. (I should have known this, I worked night shift security at Ohayocon, they enter all the time.) So along our way, we were accosted by two panhandlers. I didn't have a problem with him because I knew where he was coming from, but my date at the time was kind of sheltered, from Carroll Ohio. So she was understandably pretty nervous. Still, the dude was asking for food, not money, so we bought him some fries. The second dude was pretty cool. Just a student who was failed by the system and thrown on the street. But he knew a lot about etymology and stuff, so we started to talk. He didn't ask me for anything more other than to listen to his story, because he didn't really have anyone to talk to about his problems. So I stayed a bit ad listened. But we were hungry, so we moved on. Then there was this third guy. Not homeless, just on drugs and trying to remember where his home was. So I stopped to see if he was alright, what he was tripping on, and perhaps bring him in with us to keep him from wandering into traffic. He understood the state he was in, but had no way to figure out or remember how to get back to his brother's place. So for the most part, he was lucid, but he would always just look off into the nothingness and just zone out. We decided to buy him some wings to help digest what was in his system, but halfway through waiting for the order, he suddenly stood up and was like "I might know a way!" Then sprinted out and down the ally beside the building. Leaving the two of us just like '... Maybe we should wait for him to come back for his wings.' Well, after waiting an hour and never seeing him again, we decided just to head back to the arcade. I've only been on like five dates in my life, and from what I could remember, most of them were pretty normal and didn't go anywhere. This one did strike me as one of the more awkward ones, but it was less of a "Date" and more of a casual meet up, so perhaps it should have posted it somewhere else.