Can You Beat These Two Horrible Date Stories?

Ive decided to give you a depository where you can vent your bad date stories. So let me get the ball rolling. Here are two terrible ones from the dating files from two of my friends: Margaret You all remember my d...

I've decided to give you a depository where you can vent your bad date stories. So let me get the ball rolling. Here are two terrible ones from the dating files from two of my friends:


You all remember my dear Southern friend Margaret (the one who went out with the guy with the hairy back). She is one of my greatest sources for terrible date stories. One of her most harrowing dates occurred at her Debutante (opens in new tab) Dinner. Yes, you read that correctly.

Margaret's Debutante Dinner was a gala event. Even her 87-year-old grandmother made it, something that impressed the entire family. Her on-and-off boyfriend at the time, Jake, "invited himself" to be her date, promising that he'd behave—despite his history of reckless behavior on dates.

Jake's promise evaporated faster than a gasoline puddle in the sun. After dinner, Margaret went to her hotel room to change into her ball gown. In the meantime, Jake decided to "tailgate" the ceremony. He found Margaret's friends in a hotel room and proceeded to down an entire bottle of Goldschlager (opens in new tab). Wasted, he headed back to the ballroom and accosted Margaret's grandmother. Margaret found him muttering about fishing and pried him away from her grandmother. After returning to their hotel room, he promptly got bored and left, informing Margaret that he was going to "look for drugs". He then walked up and down the halls of the most luxurious hotel in Richmond, VA—the Jefferson (think the Overlook hotel in Stephen King's The Shining)—asking guests in every room if they knew where he could score some Ritalin.

Lighting, Hall, Interior design, Ceiling, Light fixture, Function hall, Lobby, Interior design, Column, Decoration,

(Image credit: Archives)

Upon his return to the hotel room, his drug run coming up empty, he propositioned Margaret and her female cousin for a threesome. After Margaret turned down his romantic request for an incestual threesome, he passed out drunk. Sadly, Margaret continued to be his on-and-off again girlfriend. The other day she announced: "ah don't think we ev-uh had sobe-uh (sober) sex in three years of bein' togeth-uh".


Veronica met Bill at a hockey game. Keeping in line with cliché, Bill bought Veronica a drink from a few rows back. After Veronica was told "compliments of the gentleman in Row 15", the two exchanged details.

Bill reached out via a series of hastily written emails that looked like the work of a mad man.

"we shuld get together some tme soon. maybe ew should gte a drink or smothing?"

There were so many things wrong here. This guy didn't even have the courtesy to check his email over for general clarity and spelling. This sat poorly with me because I intensely check over my emails, edit, cut, copy, paste and have two girlfriends check for "general creepiness" until the training wheels are off and I can write them on my own.

Unfortunately for Bill, he had no helpers. Veronica, after ignoring my advice not to go with him due to the fact that she cringed every time she got an email from him, agreed to meet for drinks after work at the rooftop bar of the Gansevoort Hotel.

Swimming pool, Dusk, Fluid, Evening, Reflection, Real eazstate, Horizon, Composite material, Bridge, Resort,

(Image credit: Archives)

Even though Veronica had said she was coming alone, Bill decided it was appropriate to bring two friends with him. He also decided to get drunk before she even got there. Bill also thought it was a good idea to be extremely aggressive. After lighting his cigarette in the bar with a candle holder (no smoking allowed in NYC bars), he started to make it known that he wanted some action. The over-aggressiveness culminated in groping to the point where Bill had a hold of Veronica's bra in the back and pulled it until it snapped (the old move popularized during 8th grade recess). She ran into the bathroom and called some friends to find out where they were and frantically left the bar to meet them.

A week later, Bill made the situation twice as sad and awkward when he emailed her:

"hey haven't headr from you in a while. was it sumething i sed?"

Amazing how guys like this never think they did anything wrong with a girl, while I'm always thinking I did something wrong no matter what.

So there are some examples of awful dates. Can you top these? Do any of you feel that you are just magnets for horrible dating experiences? And have you ever stopped seeing a guy because he is a total jerk when drunk, even though he's fine when sober?