Saturday’s Memoirs: Adventures in Bad Online Dates — What Kind of Underwear?

  • Posted on: April 9th, 2011 by

By J.R. Reed aka Sexandthesingledad

I don’t remember which dating website I met her on. I don’t remember her name and I remember very few things about her. I do remember what she was, or rather wasn’t, wearing when we met for our one and only date. I do remember when I was talking with my friends I referred to her as The Disney Chick. That much I’m sure of.

We traded a few e-mails, talked on the phone once and decided we wanted to go out, but she was unsure when she could. That first Saturday afternoon, she called to ask if we could meet for a couple of drinks around 7. She wanted to meet at Downtown Disney since it was halfway between her place and mine and because it was a Saturday night it would probably be pretty happening. I quickly agreed.

The Disney Chick beat me there, and she looked pretty good. We hugged hello and decided to walk around a bit before we got a drink. We picked Uva Bar because it was outside and we could enjoy the nice weather, talk and laugh at tourists.
I’m not sure why it’s so much fun to laugh at Disney tourists, but it is. I don’t remember what she ordered but I do remember it was hard liquor on the rocks. This chick was definitely not a wine sipper. I liked that.

About 30 or 45 minutes into the conversation we ordered another round–probably our third. Maybe the fourth. We were having fun. She and I were sitting at the bar and it was a bit crowded, so we were pretty close to each other. I know that our legs were touching and that on a couple of occasions she had leaned over to grab something off the bar and her rack brushed up against me—on purpose I’m pretty sure. As I recall, she had a nice set. Not overly impressive, but nice nonetheless. For the record, I wasn’t complaining about them brushing up against me.

When the bartender delivered the aforementioned drinks, she took a sip, looked at me and asked me what kind of underwear I was wearing. I gazed at her, took a long, slow drink of my Jack and Coke and said, “Boxer briefs. Why? What are you wearing?”
“I’m not wearing any,” she replied. I looked at her for a moment and said “bullshit.” She then proceeded to stand up, push herself against me, unbutton the button on her jeans and grab my hand and move it down the side of her leg. “Holy crap,” I thought. She isn’t wearing any.

She slowly moved my hand back up (she still had her chest pressed against me) and quietly asked if I was sure that I was wearing boxer briefs. “Pretty sure,” I told her, with a gleam in my eye. She stared at me with a mischievous look and whispered, “Let me check.” And with that she stuck her hand down the back of my jeans and grabbed my ass.

I think it’s safe to say that the flirting was on! We kissed a few times, had a couple more drinks and she asked me where I was parked. I told her that I had a pretty good spot and she said, “I guess we can go to my car. I purposely parked way in the back.” I got the bartenders attention and paid the check. She grabbed my hand as we left the bar, passing all the families with screaming kids as we headed towards the parking lot.

We got about halfway through the lot and she started fumbling through her purse. After a couple moments I asked if she was having a hard time finding her keys. “Nope,” she replied. “The keys are right here. I’m looking for a condom.”

  • Jennyhellrung

    Ack – you can’t stop there. What happened? I’m sure you didn’t go through with it. . . .

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About Jennifer

Jennifer Kelton

Jennifer Kelton CEO / founder LLC is a Los Angeles native and a pioneer in the worldwide dating industry, investigating the game of love while providing encouragement and support since 2007, starting with the acclaimed dating book Don’t Use My Sweater like a Towel. An accomplished CEO, visionary and entrepreneur, Kelton’s work in the […]

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