Your Worst Dating Stories

[Larry Schuler]

Worst dating experience was pretty mild.

Met on OKCupid. Got physical a few dates in. Next day, she said she didn’t think she wanted to keep seeing me. I was pretty OK with it/not upset at all/understood. She immediately changed her mind and wanted to double down commit to me and I was already checked out after being let off the hook. She cried and sent me emails and texts, some saying I’m awesome, some saying I’m mean. I knew someone who knew her and asked them to check on her. After that, I never heard from the woman or the mutual acquaintance ever again. And I was ok with it. #twentyfiveyearsold #oknotbeing25anymore

[Ky Fried Redleg]

I've waited. it seems like, all my life , to hear a Larry Schuler dating story. More, please...

[mash3024]

Connected with a girl on Yahoo Personals. Briefly chatted and decided to go on a dinner date. We were seated in a small booth and she decided to sit on the same side as me. Then we had an annoying waiter that fed into the "cute couple" schtick from the get go and she ate it up. I remembered when I first saw her she had an abnormally large purse, not sure why that stuck out but it did. Fast forward, the reason for the big purse was because she brought an entire family photo album and started going thru it at the dinner table. Then with no prior conversation about this topic she hit me with the "oh, and here's me and my dad" photo with her sitting on his headstone. Easily the most awkward first date I've ever been on. Promptly cancelled the Yahoo Personals profile after that one.

[Roy Tucker]

Ok, I’ll tell this story.

Worked with this woman for a few months and we seemed to get along so I asked her out. She said I thought you’d never ask (I was recently divorced and was reluctant to get back in the game). She we made a date.

Went over to her house to pick her up. She wasn’t quite ready so she invited me in. Went into the kitchen and there was a guy there. I thought hmmm but it was Yellow Springs and that kind of thing was common there so I didn’t think any more of it.

Took the girl out and we had a good time. Asked about the guy and she said he’s just a housemate and no romance there. We had some drinks (lots of drinks) and she invited me back to her house. Got back to her house, things warmed up rapidly, and she said let’s go to the bedroom to which I was quite amenable.

Went in the bedroom and roommate guy was there sleeping. I was like uhhhhh wtf. She said it’s cool, he’s cool, and he might join in. I went uhhhhh again and said I’m not quite into such things. So I headed out the door, she tried to get me to stay, and I said ahhh no.

If it had been a female roommate I might have stayed. But I’m decidedly hetero (or whatever the term is now) and it just didn’t appeal to me. We stayed friends and she and roommate guy eventually got married so I don’t quite know what the story was that night.

[Larry Schuler]

Connected with a girl on Yahoo Personals. Briefly chatted and decided to go on a dinner date. We were seated in a small booth and she decided to sit on the same side as me. Then we had an annoying waiter that fed into the "cute couple" schtick from the get go and she ate it up. I remembered when I first saw her she had an abnormally large purse, not sure why that stuck out but it did. Fast forward, the reason for the big purse was because she brought an entire family photo album and started going thru it at the dinner table. Then with no prior conversation about this topic she hit me with the "oh, and here's me and my dad" photo with her sitting on his headstone. Easily the most awkward first date I've ever been on. Promptly cancelled the Yahoo Personals profile after that one.

I feel bad for that lady. That reads as both very lonely and very naive and imagining people (rightfully) being taken aback or (less rightfully) making fun of her gives me fourth-hand sadness. Always kinda triggering for me when I see/read about adults who do things that can be viewed as very child-like or naive. Reminds me that there is a part of us that is still a kid/longing for that kind of naive outlook on the world around us. Anyway, what a bizarre date.

[Ky Fried Redleg]

Ok, I’ll tell this story.

Worked with this woman for a few months and we seemed to get along so I asked her out. She said I thought you’d never ask (I was recently divorced and was reluctant to get back in the game). She we made a date.

Went over to her house to pick her up. She wasn’t quite ready so she invited me in. Went into the kitchen and there was a guy there. I thought hmmm but it was Yellow Springs and that kind of thing was common there so I didn’t think any more of it.

Took the girl out and we had a good time. Asked about the guy and she said he’s just a housemate and no romance there. We had some drinks (lots of drinks) and she invited me back to her house. Got back to her house, things warmed up rapidly, and she said let’s go to the bedroom to which I was quite amenable.

Went in the bedroom and roommate guy was there sleeping. I was like uhhhhh wtf. She said it’s cool, he’s cool, and he might join in. I went uhhhhh again and said I’m not quite into such things. So I headed out the door, she tried to get me to stay, and I said ahhh no.

If it had been a female roommate I might have stayed. But I’m decidedly hetero (or whatever the term is now) and it just didn’t appeal to me. We stayed friends and she and roommate guy eventually got married so I don’t quite know what the story was that night.

She wanted a Menage a tROYs