The Breakup

The photographer showed one of her works to her lover and asked what he thought the people portrayed in it were like. She quietly walked out a few moments after he—feeling flustered and taken off guard—replied, “I don’t think photographs can tell you anything.”

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Rating: 4.5/10 (8 votes cast)

Bad Move

On their first and only date, he tried to compliment her, “I wish I’d met you twenty-five years ago, because, you know, you’re pretty now and all; but you probably could’ve stopped traffic then.”

She narrowed her eyes and cocked her head to the side as if examining him and then replied, “I can’t tell about you—were you ever attractive?”

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Rating: 9.3/10 (19 votes cast)

Pride and Prejudice

Before boarding the train to a beach town, I once laughed heartily at a guy with oversized glasses and over-gelled hair. Weirdly, on the evening train back into town, he attempted a Back Street Boys’ medley in broken English and somehow won me over to the idea of sharing a gelato.

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The Right Fit

She dated around for years, and there were guys she probably would’ve married if things had gone differently, if they had stuck around long enough to ask. It wasn’t until Boyfriend #63 that she realized what a mistake and a misery that would have been and what she would have missed out on by settling.

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Rating: 7.0/10 (5 votes cast)

False Modesty

He had an intense fear of appearing conceited and took great pains to make light of his accomplishments or to avoid discussing them altogether. At first, she confused this with modesty and found the trait endearing; but eventually, she recognized it as the height of arrogance: he must believe himself to be a living miracle, given the amount of time and energy he expended in convincing people it was not so and worrying that his presence in the room might make them feel small.

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The disease he contracted was not life-threatening, but it scared him enough that he turned his routine upside down and dramatically altered his diet. In the end, that brief scare and the changes it prompted added ten years to his life.

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He worried about her sister and pleaded with her a million times to end the affair until he finally realized that it filled some void, some need that she had. He knew she wouldn’t stop until it appeared to her that this no longer satisfied that need.

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Rating: 7.7/10 (9 votes cast)