Winner and Dessert

Story Submitted by Reuben:

Deborah and I met at a dessert place for our first date.  She was an engineer, and also very attractive – a tall blonde with a great smile.  She seemed very excited to meet me, and I felt the same way.

When we did meet in person, though, the truth came out.  "Down to brass tacks," she said before we had even ordered, "I'm not interested in you for me.  I have a little sister, Margaret, who just got over being a lesbian and I'd like to set her up.  Someone like you would be perfect."

The statement was so loaded, it's a wonder that her back didn't buckle under the weight of it.  I said, "I was under the impression that you were interested in me."

She said, "I know, and I'm sorry.  You're not my type.  You're probably my ex-lesbian sister's type, though."  She pulled out a picture of a girl who looked like Deborah's exact opposite: short, squat, overweight, and with short, dark hair.

I had to ask, "Who's this?"

"My sister.  She said that she wants to try dating guys now and I'm helping her."

I asked, "Why me?"

She said, "You two have a lot of the same interests.  Plus, you seem like a really good guy.  You could probably teach her a lot."

I studied the picture, then handed it back to Deborah.  "Sorry," I said, "I don't think so.  I don't feel comfortable with this set-up."

Deborah said, "Why not?  She's great."

I replied, "Because I spent the past two-and-a-half weeks thinking that you were attracted to me.  That's not suddenly weird or awkward to you?"

She said, "No, but it seems to be for you.  I'm used to guys being attracted to me.  I picked you out because you seem nice, and also a little desperate.  I'm trying to help both you and my sister, here.  A little gratitude would be nice."

I said, "Is your sister also a manipulative, disrespectful little brat like you?"

Deborah smiled, rolled up the photo of Margaret, placed it in her purse, and said, "Then never mind."  Then, to my surprise, she said, "Let me order you a dessert.  My treat."

We both ordered dessert, made very awkward small talk, she paid for both of us, and she even hugged me goodbye.  I have no idea what went through her head, but I'm probably better off not knowing.


  1. I'll never understand..

    ・The rest of the date was silent after that
    ・Dinner was awkward afterwards
    ・We watched the rest of the concert in silence (after she tried to nick my wallet)
    ・We didn't talk much after his/her *insert outlandish, ridiculous, stupid behaviour*
    ・We carried on hiking after my date had said "Let's switch partners for the rest of the hike and meet in the parking lot"
    ・I tried to salvage what remained of the date after being disrespected/yelled at/demeaned/etc

    Basically I stayed when I could've left and similar variations.

  2. Probably because leaving in the middle of a restaurant meal or concert is extremely awkward and most people are really reluctant to do so even if their partner is being a jerk.

  3. I agree with Sawyer. My love life improved so much after I learned to simply say "Sorry but this is a dealbreaker, goodbye."

  4. Dudes, perhaps you missed this little tidbit:

    Deborah smiled, rolled up the photo of Margaret, placed it in her purse, and said, "Then never mind." Then, to my surprise, she said, "Let me order you a dessert. My treat."

    Why be an ass at this?

    Yes it was rude and deceptive, but why jump up and make a scene? He had already asserted himself in this story perfectly.

    Enjoy the free dessert and leave without being an ass about it.

    ... That said... I do get bad vibes about family trying to convince a lesbian that she's not really a lesbian.

  5. She offered to pay for dessert after he called her a manipulative, disrespectful brat. He had to make his point and feelings known before she felt bad enough about leading him on to offer compensation.

  6. Sucks, but hey, free dessert. Nothing wrong with that.

  7. Wait. Why was she rolling up the photo? Was it on a piece of paper that was rollable? Most pics are small or on harder paper or if they have been printed on regular paper, they would be folded, not rolled. I don't know. That part seems strange.


Note: Only a member of this blog may post a comment.

Content Policy

A Bad Case of the Dates reserves the right to publish or not publish any submitted content at any time, and by submitting content to A Bad Case of the Dates, you retain original copyright, but are granting us the right to post, edit, and/or republish your content forever and in any media throughout the universe. If Zeta Reticulans come down from their home planet to harvest bad dating stories, you could become an intergalactic megastar. Go you!

A Bad Case of the Dates is not responsible for user comments. We also reserve the right to delete any comments at any time and for any reason. We're hoping to not have to, though.

Aching to reach us? abadcaseofthedates at gmail dot com.