Story Sent in by Steve:
I had become acquainted with Maryann online. She was adorable, and could've passed for a young Rita Hayworth. She was also very bright, having earned two master's degrees. To say that I was excited about scoring a date with her was an understatement.
I took her out for coffee on a warm spring night. She was in a pair of dark jeans and a floral blouse, and she looked great. We had a good chat together, and I asked her if she wanted to take a walk.
While strolling through town and through a park, I couldn't help but notice that her pants were practically falling down. I thought that it would be the polite thing to inform her (before they fell down even further) and I said, "You might want to pull your pants up."
She gasped, her eyes widened, her face went blood red, and she yanked her pants up far higher than was necessary. "Oh my God," she said, "You weren't supposed to see that."
I said, "It's not a big deal. It's not like I'm offended. I just thought you'd probably want to know."
"You weren't supposed to see that. Oh my God. Oh my God. You weren't supposed to see that."
I joked, "See what? I didn't see anything, although I probably would have if I had waited another minute."
She stopped walking and readjusted herself so that her pants were riding stupidly high, way above her stomach.
I laughed a bit and said, "That can't be comfortable."
She asked, "Are they not high enough?" and then pulled them up even further, which I hadn't thought possible.
I said, "Maryann, I don't think you're really helping matters. They've been fine for most of the evening. Just keep them regular and be conscious of them and I'm sure you'll be fine."
She kept her fingers curled tightly around the waist of her jeans and walked around like that for the rest of the night. She cringed a couple of times as if in some sort of pain, but I tried my best to not indulge her performance with "Are you okay?" or "Why are you doing that?"
At the end of our walk, I finally turned to her to say, "Are you trying to prove some sort of point?"
In answer, she stuffed her arms down her jeans. Now they weren't going anywhere. I said, "Okay, then. I'm probably going to go. Have a good night."
"I'd hug you," she said, "But my arms are kind of down my pants."
"Don't worry about it."
Neither of us contacted the other after that. I hope she bought a belt.
Story Sent in by Steve: