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I spilled my coffee and said, Oops, guess that means I should go. They arrive, and I do enjoy them! Funniest dating site fails still have the red velvet box. I think, what the hell, I have done one or two insecure things in my time, I should give the guy a break. So I meet him at a bar, and he proceeds to be very very silent. Go ahead and tell me what I am. I never pulled taffy. So I try the usual: What do you do? I ask him if he has any siblings, and that was the question. Maybe this was a good date for him. He was sweet, intelligent. Anyway, one day, we meet. I pick him up in my car.

Lo and behold, he is really, really ugly. Terrible acne, overweight, just… kind of repulsive. Since I was going there anyway, my brother asked me to pick him up some beer. The date consisted of me meeting the woman at her apartment, and finding she was already pretty drunk. We went out to eat at a steakhouse she insisted I drive her Camarowhere she berated the waiter so badly and for such a trivial reason that I found the manager while she was in the bathroom and apologized. We had time to kill before our movie, so we went to a bookstore. While at the bookstore, I mentioned that at some point I needed to go to a store and buy some beer see reason above. We agree on a restaurant in another, distant-ish part of the city, and dude decides he wants to walk there instead of taking the subway.

Though my boots have annoying heels, I try to be a good sport and agree. He insists that instead of dinner, he absolutely HAS to take me to his absolute-favorite-in-the-whole-world gelato shop, which just happens to be a couple of blocks away. So we enter this tiny, tiny gelato shop, and I notice that there are only two chairs — stools, really — in the whole place, placed very close together in a tiny corner with a tiny little counter, and I start to get nervous. I turn away from dude to look at some display of artisan chocolate or something and surreptitiously gnaw my hand.

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I have to take some ownership of this bad date — I should have been way less polite and more assertive about my own needs. We made arrangements to meet at a stuffy Cambridge watering hole. And she was not happy about it! I, on the other hand, was mortified. This fraction of a second set the tone for the rest of the evening which was to be predictably briefand we soldiered our way through a single drink together which as I may have mentioned was actually my second, thank god. She was not only visibly displeased with our little arrangement but went out of her way to make this as evident as possible: In short, it was the most excruciating half hour of my professional dating life.

As soon as we both realized there was most certainly not going to be another round she started angrily protesting the inattentiveness of our actually perfectly attentive waitress I guess because I was so off-putting that the bill had to be paid RIGHT NOW and she got up and stormed off to the bathroom. So we walked out together. Meanwhile, the train pulled into the Kendall Square stop, and in brief flash of genius I hatched an escape plan: How You Start Thinking: He sang songs on my answering machine, either telling me how he deserved another chance or telling me what a huge bitch I was. I met men who told me they were single and then three dates in told me they were married.

I met a man who said he was 45 but was probably I met a man who showed up faking an English accent, wearing satanic goat-head jewelry, and wearing a girdle — I only know about the girdle because the cops shook him down. Since I am the common denominator in all these disastrous dates, I think the problem is me. I must have had a terrible screening process. We met at a bar, and she was super attractive I really wanted to bang her but also wanted to be a gentleman so I deferred to conversation. We talked for 6 hours.

She came over to my place on that Sife where some friends and I were gails a fire. She Funniest dating site fails me at 2AM from inside Funiest house asking if she could stay over after taking her friend downtown. She stayed over and we had awesome sex. We continued having awesome sex every day that week. And we actually had a lot more in common then sex. Like birds and stuff. Then she mostly disappeared. She wrote me a big ol email about being busy for a while she was finishing her thesis and I was dumb in ignoring the writing on the wall. And this book on the history of graphic design that she said was her favorite.

A few weeks went past, and I emailed her to see if we could meet up to exchange our stuff. She had my binoculars. Then she moved to Iowa with my fucking binoculars. But I still have her pillow and book.

A Treasury of the World’s Worst Online Dating Stories

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