Jessica is a writer, Brian a publicist. Jessica's got her shit together, Brian crashes on friends' couches in Brooklyn and channels all his earnings toward paying off his two DUIs. And yeah, living in New York is so bad it is possible in certain situations at certain points in life to find those traits actually endearing, especially if you tend to spend an inordinate amount of time with publicists. And so Jessica found herself in a semi-whirlwind six-day relationship with Brian during which she also found herself, surprise surprise, paying for everything. Which, in itself, would not be so bad. But Brian had an entitlement about him — I know! ENTITLEMENT, such a rarity in the males these days!! — that got tiresome; it was almost as if he found himself so interesting (of course he did!) that his company made it all worthwhile, and she started to sense he was kind of immature, and he began to sense her sensing that, and so the two made another date; Brian's treat this time. (This is sort of like the time this one friend of mine had to pay for the Valentine's Day dinner to which her boyfriend of six months invited her, just saying.) Anyway, they went to a cheap cafe, and the bill came. "I only have $40 in cash, can you cover the tip?" Brian asked. Jessica only had a credit card, so she agreed to pay it and take the cash. "Wow, some date!" she remarked. "But I'm broke!" he replied, and she rolled her eyes and took his money, only to find, in the cab ride home, that he'd only given her $18. "Oops!" he said when she called, "Here's the other twenty in my wallet! Silly me!" And then sent this beauty.

Dearest Jessica,

You have totally turned my insides inside-out. For once in a long time, I felt I had met someone I could connect to. Now, I want to throw up. I smell your stupid lip gloss on my lips as I'm writing this, and I am disgusted with myself for having it on my mouth.


20 dollars? I would've gotten right back on the subway and given it to you if I knew you were going to be so cordially fucked about it. Obviously, this is a sign of other things to come, and I'm glad I got out before I started thinking you were amazing, or something.

You're actually average. And rude. And I feel totally abused, after only a week of knowing you. I feel bad for other guys you might do this to in the future. I'm sickened by the kiss you blew to me the night we had that wonderful date and we parted ways. I'm SICKENED by it.

Sorry I couldn't please you. Thanks for being so understanding. Or not.

You can go back to your hockey player now. I hope he treats you terribly, and I hope you have many sleepless nights of running mascara and tear-stained pillow cases to look forward to.


Thanks for giving me the smallest chance. Now you can take that chance and go screw yourself with it.