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Beau woes: Boyfriends who just don’t cut it

‘58 Bad Boyfriend Stories’ that make a girl want to stay single

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Feb. 21: TODAY’s Hoda Kotb and Billy Bush talk to Barbara Davilman and Liz Dubelman about their book of bad dating stories, “What Was I Thinking?”

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updated 11:52 a.m. ET Feb. 12, 2009

Ranging from hilarious to pathetic, the true tales of "What Was I Thinking? 58 Bad Boyfriend Stories" all describe the moment when logic, common sense and simple self-respect triumph over the need to be loved. Basically, the moment when a woman finally realizes, "It's over." An excerpt.

"Junk in the Trunk" by Amy Wruble
I knew it wasn’t going to work out with Phil about halfway through our first date. Bobby, eager to pair off his single friends, had invited both of us to dinner in SoHo without much thought to our compatibility. Phil was short and slender, with small, pointy, feminine features, like a ferret in drag. I wasn’t going to let his looks thwart the possibility of romantic connection. It was January and I’d just made a resolution to be less superficial in the New Year. All my life, I’d been a single white female seeking an intellectual male supermodel. (Have you met my husband, Dr. Matthew McConaughey, M.D., Ph.D.?) This was a lot like trying to date the Loch Ness Monster. I was ready to admit that the species was just a myth.

Along the way, I’d dated a string of sexy scarecrows, still waiting for The Wizard to grant them a brain. There was the chiseled musician who can best be described as half-lingual. His rock band should have been called Malapropism. He once ordered the “cheese fondude.” There are only so many times you can shut somebody up with kisses, especially in a restaurant. Then came the adorable pot dealer whose remedial math skills almost got him beat up when he shortchanged a client by confusing a pound with two half ounces. A high school drop-out, he lacked book knowledge. (His Achilles’ heel was not knowing where his Achilles’ heel was.) Dating these cute dopes had left me with nothing but pretty photographs, huge credit card bills, and an STD scare. But Phil, my blind date, came from a nice family, went to a good school and had a big-boy job in finance, so I was going to look right past that girlish rodent face into his beautiful (I hoped) soul.

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The restaurant was small and unpopular. We ordered drinks and appetizers and got to know each other a bit, with Bobby playing host. “Phil, you and Amy have something in common. You’re both from Connecticut.” Me: “Really, what part?” Him: “Westport.” Me: “I’m from Stamford.” Him: “Oh.” So maybe we didn’t have a cosmic connection, but I was still cheerily optimistic that Phil had something charming or special about him waiting to be revealed.

At some point I got up to pee, locating the tiny, drafty bathroom across the way. There I was, jeans down around my ankles in the stall, when I heard voices, loud and clear, like they were next to me. It was Bobby asking Phil, “So what do you think of Amy?” Through some trick of the acoustics, the sound of their conversation had traveled up into the ceiling rafters and down into the bathroom as easily as water through pipes. “She’s a nice girl … ” Phil began. I stopped peeing so I could hear even better. This was a rare opportunity, the realization of that fantasy where I’m invisible and can hear what everyone’s saying about me. “But you know,” Phil continued, “she’s got a lot of junk in the trunk.” I was stunned. If this had been a reality show, one of those record-scratching sound effects would have really captured the moment.

For anyone not familiar, “junk in the trunk” is a derogatory reference to the size of a woman’s behind. So let me set the record straight about my ass, before it sues me for slander. My ass is one of the least objectionable parts of my body. It’s round, it’s firm, it has pizzazz. And ever since J-Lo and Beyonce embraced bootyliciousness, it’s even trendy. If my ass had a job, it would be entertaining the troops in the USO. If my ass had a name, it would be Lola. My trunk has spunk. Now, had Phil directed his critique elsewhere, say, my training bra boobs or the premenstrual volcano on my chin, I might have stayed locked in the bathroom all night, tearful and humiliated. But his critique wasn’t so much hurtful as ironic. Here I was, renouncing my superficiality, pledging to embrace inner beauty, and the ferret face thinks I’ve got a big butt.

I returned to the table, wondering how and when to expose my secret knowledge. (You didn’t think I was going to let this one slide, did you?) The opportunity presented when the waitress asked if we wanted dessert. Phil turned to me: “Do you want to split something?” I paused, looked deeply into his eyes, and told him, “I don’t think so. I want to be careful not to put too much … junk in my trunk.” Something flickered in his face. Phil didn’t acknowledge my comment, but I knew he’d heard me. I wondered if he thought I was psychic, or just had supersonic ears. I wondered if he felt guilty or was simply relieved to know our brief relationship had come to an end. (Insert record-scratching sound here again.)

In that moment I reevaluated my New Year’s resolution. Maybe it’s okay to be a little superficial. When I’m genuinely attracted to a man, I’m flirtier, warmer, and a better date, making him more likely to appreciate my total package instead of appraising my parts. Maybe I just need to balance physical attraction with some deeper qualities like kindness and being good at Scrabble. Months later, I heard Phil turned gay. Okay, that’s not strictly true, but it’s what I like to tell myself, and Lola.