Your Awful Story Olympics, Vol. 2

It’s been a month since our last edition of the Awful Story Olympics, so how about we pop open the computer mailbag and see what falls out?

Awards for the craziest emails I’ve received in the last thirty days…

The Bronze:

I have an embarrassing story for you. Well I guess it’s embarrassing. I went out with this guy who was a few years older than me, probably like 40. I’m 28. Anyway, we hung out for a drink and it was pretty fun, then he asked if we wanted to go back to my place and smoke some “grass.” He seemed harmless enough, and I’m always open to free pot, so I said sure. Well, we got back to my place and sat down and he said, “ok, let’s smoke!” and waited for me to take it out! He didn’t have any pot?!! I told him I didn’t either and usually when you invite someone to smoke you have some with you. He just laughed and said “sorry!” – Shayna (Brooklyn, NY)

Aaaaand that’s when you got murdered. You invited a guy 12 years older than you back to your apartment on a first date?! And the worst thing that happened was he didn’t have any weed? That’s not an embarrassing story, that’s a miraculous success. You’re insane. Don’t do that again, Shayna. Ever. Any part of it. I don’t have enough readers to be losing any to homicide.

The Silver:

An email I received from reader Gary H., in Toronto, Canada. (That’s right, we’ve gone international, bitches! Sort of!)

Michael Scott giveth, and Michael Scott taketh away.

I had a girl [I met online] come over and cuddle with me for a night, and it turned into some hanky panky. She slept over. I guess I should have noticed a red flag, but she let me see her naked so I let it slip. She brought over “The Office” which shows she had a great sense of humor so I figured there wasn’t anything to worry about. So she ended up leaving a blanket at my place, The Office and some other things and I figured she was looking to date. Which is great, because I am too. I’m not looking to get married, or anything super serious unless it turns into that, regardless all signs pointed to an exclusive relationship with benefits and I was thrilled to say the least. I texted her on the third day of our sleep overs, dinners and intimate adventures, and I asked if we were exclusive. And she said “No. I have to get to know you better.” Well you already know my penis, so I assume you and I know each other pretty well. I may not know your deepest darkest secrets, but I had already met her parents (we spent a ton of time together within the three days).

I was so confused. I don’t get it.

I love this email. There’s clearly such a tangled web here, I can’t wait to get an equally perplexed message from a girl asking to know why this guy she met in Toronto totally went overboard when she happened to leave an Office DVD at his place. She’ll say “I mean, I only knew his penis, what’s the big deal?”, and I’ll have no idea who to side with. Parents were met in three days?! What exactly is an “exclusive relationship with benefits?” Don’t most exclusive relationships come with benefits? Unless, wait, are we talking about actual health benefits? I’m so confused. Silver medal!

The Gold:


I wanted to share this lil’ beauty with you. It’s just so terrible on so many levels! It was especially painful to read as a grammar freak…

Ever been to an ‘Owl Party’?

Don't look at me. I've got no fucking idea what an owl party is either.

Do you like sweets? I do, and I think it runs in the family. I had been faithful to my diet and working out for a steady length of time. But alas i have relapsed. 7/8 of a medium pizza and cake and ice cream and I still baked cc cookies at 1 in the mourning. What a splurge. However I did take control myself and only had one. Something about these cookies was off (maybe they were to dry). They lacked that O’ so rewarding gooey center. These were more like a dollar store knock off brand gone bad. Well, of to and extra long gym session. How many calories in a pizza pie?

P.S. Would u like some totally awesome chocolate chip cookies? their fresh. -K.N., (Nashville, TN)

You know what, K? That would be painful to anyone, grammar freak or otherwise. I think he actually got more things wrong than right.

Oh, and here’s a tip fellahs, if you’re considering listing everything you ate in a hysterical night of crazed binge eating to someone you’ve just met online and are hoping to see naked…don’t. Just don’t. It, well, it makes you seem crazy. Even if you’re in amazing shape, eating pizza and ice cream and cake and cookies all in a row seems like the sort of thing John Hinckley would’ve done before trying to shoot Ronald Reagan. You might as well tell them you’re really into Catcher in the Rye. And just for the record, 7/8 of a pizza doesn’t count as “sweets.”

And come on, what the hell is an owl party?

Get in on the fun. Send me your dating disaster or horrendous email here.

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3 Responses to Your Awful Story Olympics, Vol. 2

  1. Jen says:

    Worst part of gold medal story: he offered her cookies that he had already admitted were sub-par. RUN GIRL!

  2. Denise says:

    I need to date more interesting people.

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