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Posted: February 3, 2014

Contest: Win $50 to Caiola’s! Tell us your Best Worst Date Story

Written by: Staff Reports

Congrats to Jennifer Roche!

Jennifer’s worst date story won us over with its…grossness. Her date is one most of us wouldn’t wish on our worst enemy. That said, it was a tough choice. There were a bunch of excellent (and horrifying and hilarious) stories, so thank you for sharing them with us.

Jennifer’s story

“Everything started out fine, but ended terribly. We had arranged to have a casual evening together, you know: movies, wine, talking. When he arrived we poured some wine and started talking at my kitchen table. As he was holding my hand and everything was going well when I began to notice that he was sweating, not just it’s a little bit hot in here sweating, sweating to the point where he had a not so sexy sweat mustache and beads rolling down the sides of his face. I asked if he was alright or if he was too warm. His response was that the wine was getting to him a little bit (two sips in I might add) and that he wasn’t feeling that well. Suddenly he gets up, proceeds to take off his sweater and start pacing my apartment. Starting to become concerned, I ask if everything is okay or if there is anything that I can do. He replies no.

“After about two minutes of this constant pacing, he blurts well I guess I should get it over with then, walks in to the bathroom of my tiny studio apartment and proceeds to vomit for a solid 15 minutes. I can hear everything, and I mean everything. I just sat awkwardly at the table, questioning my effect on men and finishing my glass of wine. While pouring myself another glass he emerged from my bathroom looking still as sweaty, but a little less haggard. I politely give him an easy out by telling him I know it sucks to be sick anywhere, especially somewhere unfamiliar, and that I understand if he wants to go home. “Do you want me to leave?” he replied accusingly. Taken aback by his harsh response, I proceeded to offer him a glass of water and ask him if he is feeling any better. He said that he still feels ill, but would like to watch a movie (our original plan, pre vom-bombs).

“A few minutes in, he gets up for round two of bathroom vomit. At this point I am disgusted and the only thing in the world I want is for this man to leave my apartment and bleach the shit out of my bathroom. Yet, without fail he sits back down to start the movie up once again, snuggling me even closer in the process. As he gets close, I notice little flecks of now dried vomit on his shirt and pants, trying not to vomit myself; I casually reposition so as to avoid contact with the human bile. Finally the end of the movie came at 10pm, and not a moment too soon. He starts making moves as if he wants to start making out, which I countered with a forced yawn and a tale of much needed sleep. He promptly jumped up off the couch and essentially ran out of my apartment, stating that he understood if I never wanted to see him again. Hopefully I never will. ”


$50 gift card to Caiola’s, Portland
“Regulars frequent this West End bistro for its superb wine list, good cocktails and unbeatable food.” – so says Press Herald Bar Guide writer Claire Jeffers. Read more: Cool and cozy Caiola’s a popular West End destination

NOTE: Winner will need to pick up the gift card at inside One City Center, Portland, during regular business hours.

How to enter

Easy: Simply post your best worst date story in the comments section below. Maybe it’s that time your date stole your car and spent an overnight at county. Maybe your friends set you up with someone who liked to eat hair (yours, as it turned out). Maybe your date was fantastic, but you both ended up locked in a movie theater overnight, surviving on Sno Caps until rescue arrived the next morning. Whatever the date tragedy, you can tell us. Your story will help you heal. Also: You could win $50 to Caiola’s! You can leave out the telling details (we’re not here to embarrass someone else, even if the nitwit ditched you in the middle of dinner for someone else, and the waiter had to ask you to leave because your sobbing was disturbing the other diners).

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