Is That What I've Been Doing Wrong?

Story Sent in by Ruth:

Jerry was a friend of my older sister who eventually ended up spending more and more time with me. He was friendly and very kind to me, but I wasn't sure why he'd want to hang out as often as he did. This was during a time when I was in a bit of an antisocial phase, and in retrospect, I'm sure I came off as callous a lot of the time. Nevertheless, Jerry didn't seem to mind, and we hung out at least twice a week for the better part of four months. He'd come over, we'd take a walk, watch a movie, and so on. Nothing beyond that.

We had never been out to dinner together before (although we had ordered in a bunch) and one day he came over and asked me if I wanted to go out to dinner with him. I liked the idea, and told him so.

But then, he said, "Would you mind wearing your underwear outside your clothes for the date?"

WHAT!? I didn't know what to respond to, first! I said, "First of all, it's a date? Second of all, nooooo..."

He said, with a straight face, "Have you ever been on a date, before? That's what people do."

For the record I had been on a date before (okay, two), but despite my relative inexperience, something here really didn't sound right.

I said, "I think we can go out, but just as friends. And seriously? No one's wearing their underwear outside their clothes."

He replied, "But that's what people do on dates. Hang on. Be right back." He ducked out of my room and hurried into the bathroom. When he returned, he had his boxer shorts on over his jeans.

I shut my eyes, pretend-screamed, and laughed. "Oh my God! Put it back on the right way."

"It's your turn, now."

"I'm not doing that! Go get dressed!"

He said, "Then I'm through wasting my time with you," and he left the house with his boxers still outside his pants!

I saw him a few times after that, when I went to parties with my sister, but he barely acknowledged my existence.


  1. Well, it's much easier to get a girl to drop her panties, if they are on the OUTSIDE of her pants...

  2. How much does anyone wanna bet that Jerry is the kinda dude who describes himself as a Nice Guy™ and is totally confused as to why women won't date him?

    "All the women I try to woo with my panties-on-the-outside scheme turn me down! Women only love douche bags!! Wahhh!!!"

  3. There should be a law requiring people to read bad date stories before they are allowed to enter the dating pool.

  4. So my question is: Was this guy's real name Doug and did he fight crime in the guise of Quail Man?

  5. OP saw him twice per week for four months, socialized with him in the bedroom and was surprised when he called dinner out a 'date?'

    1. What are you talking about? Did I miss something?

    2. Socialized in the bedroom? Where was that in the story?

      She was surprised he called dinner a "date" because they had hung out as friends for four months, so she probably assumed that going out to dinner was another "hanging out as friends" thing.

    3. Yes. Surprise is usually what happens when something comes out of nowhere. He should have opened with it being a date since all they've done so far is hang out as friends.

  6. "He ducked out of my room and hurried into the bathroom. When he returned, he had his boxer shorts on over his jeans."

    Safe to assume they were socializing in her bedroom.


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